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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-09-22 18:34:15 UTC

HMDB ID

HMDB0000855

Secondary Accession Numbers

HMDB00855

Metabolite Identification

Common Name

Nicotinamide riboside

Description

Nicotinamide riboside is involved in nicotinate and nicotinamide metabolism. Nicotinamide riboside was originally identified as a nutrient in milk. It is a useful compound for the elevation of NAD+ levels in humans. Nicotinamide riboside has recently been discovered to be an NAD(+) precursor that is converted into nicotinamide mononucleotide by specific nicotinamide riboside kinases, Nrk1 and Nrk2. It has been shown that exogenous nicotinamide riboside promotes Sir2-dependent repression of recombination, improves gene silencing, and extends the lifespan of certain animal models without calorie restriction (PMID: 17482543 ). Supplementation in mammalian cells and mouse tissues increases NAD(+) levels and activates SIRT1 and SIRT3, culminating in enhanced oxidative metabolism and protection against high-fat diet-induced metabolic abnormalities (PMID: 22682224 ). Recent data suggest that nicotinamide riboside may be the only vitamin precursor that supports neuronal NAD+ synthesis (PMID: 18429699 ). Nicotinamide riboside kinase has an essential role in the phosphorylation of nicotinamide riboside and the cancer drug tiazofurin (PMID: 15137942 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000855
     RDKit          3D
Nicotinamide riboside
 33 34  0  0  0  0  0  0  0  0999 V2000
   -5.3008   -0.5595   -0.0748 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9507   -0.9690   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687   -2.1002   -0.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105   -0.0501    0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450    1.1554    0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592    2.0265    1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219    1.6407    1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    0.4474    0.5408 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.7997    0.1162    0.4427 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5204    0.9145   -0.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7687    0.2943   -0.4129 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6540    0.7735   -1.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    2.1347   -1.4028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5400   -1.1841   -0.4392 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1814   -1.7577    0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -1.2644   -0.1306 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7482   -2.2785    0.7465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674   -0.3599    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6060    0.2862   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9988   -1.0552    0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2958    1.4419    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320    2.9892    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904    2.3556    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3311    0.1445    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607    0.6163    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512    0.2907   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3034    0.4575   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8356    2.3433   -0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970   -1.6770   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091   -1.3881    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5452   -1.3669   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198   -3.0975    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3106   -1.3205   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  8 18  2  0
 18  4  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  1
 11 25  1  1
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  6
 15 30  1  0
 16 31  1  6
 17 32  1  0
 18 33  1  0
M  CHG  1   8   1
M  END

  Mrv1652309042000132D          

 18 19  0  0  1  0            999 V2000
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6674   -2.1349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -2.1349    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125   -2.9195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4125   -2.9195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4521   -1.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -3.5870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -3.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -4.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  1  1  0  0  0  0
  4  3  2  0  0  0  0
  7  4  1  1  0  0  0
  4  5  1  0  0  0  0
  6  2  1  0  0  0  0
  5  6  2  0  0  0  0
  6 17  1  0  0  0  0
  7  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  6  0  0  0
 10 14  1  1  0  0  0
 10 11  1  0  0  0  0
 11 13  1  6  0  0  0
 14 15  1  0  0  0  0
 17 16  2  0  0  0  0
 17 18  1  0  0  0  0
M  CHG  1   4   1
M  END
> <DATABASE_ID>
HMDB0000855

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1-4,7-9,11,14-16H,5H2,(H-,12,17)/p+1/t7-,8-,9-,11-/m1/s1

> <INCHI_KEY>
JLEBZPBDRKPWTD-TURQNECASA-O

> <FORMULA>
C11H15N2O5

> <MOLECULAR_WEIGHT>
255.2472

> <EXACT_MASS>
255.0980966

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
24.829741468645594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium

> <ALOGPS_LOGP>
-2.27

> <JCHEM_LOGP>
-6.120781883805078

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.990744651010578

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.390918005504384

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6264200820796249

> <JCHEM_POLAR_SURFACE_AREA>
116.89

> <JCHEM_REFRACTIVITY>
60.83450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000855
     RDKit          3D
Nicotinamide riboside
 33 34  0  0  0  0  0  0  0  0999 V2000
   -5.3008   -0.5595   -0.0748 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9507   -0.9690   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687   -2.1002   -0.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105   -0.0501    0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450    1.1554    0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592    2.0265    1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219    1.6407    1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    0.4474    0.5408 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.7997    0.1162    0.4427 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5204    0.9145   -0.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7687    0.2943   -0.4129 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6540    0.7735   -1.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    2.1347   -1.4028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5400   -1.1841   -0.4392 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1814   -1.7577    0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -1.2644   -0.1306 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7482   -2.2785    0.7465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674   -0.3599    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6060    0.2862   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9988   -1.0552    0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2958    1.4419    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320    2.9892    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904    2.3556    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3311    0.1445    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607    0.6163    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512    0.2907   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3034    0.4575   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8356    2.3433   -0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970   -1.6770   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091   -1.3881    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5452   -1.3669   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198   -3.0975    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3106   -1.3205   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  8 18  2  0
 18  4  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  1
 11 25  1  1
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  6
 15 30  1  0
 16 31  1  6
 17 32  1  0
 18 33  1  0
M  CHG  1   8   1
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+1
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.246  -3.985   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.246  -3.985   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770  -5.450   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.770  -5.450   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.711  -3.509   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.675  -6.696   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.675  -6.696   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.049  -8.103   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.001   0.770   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    4                                                       
CONECT    4    3    7    5                                                  
CONECT    5    4    6                                                       
CONECT    6    2    5   17                                                  
CONECT    7    4    9    8                                                  
CONECT    8    7   10                                                       
CONECT    9    7   11   12                                                  
CONECT   10    8   14   11                                                  
CONECT   11    9   10   13                                                  
CONECT   12    9                                                            
CONECT   13   11                                                            
CONECT   14   10   15                                                       
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17    6   16   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0000855
HETATM    1  N1  UNL     1      -5.301  -0.559  -0.075  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.951  -0.969  -0.210  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.669  -2.100  -0.703  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.910  -0.050   0.236  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.245   1.155   0.761  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.259   2.026   1.184  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.922   1.641   1.060  1.00  0.00           C  
HETATM    8  N2  UNL     1      -0.583   0.447   0.541  1.00  0.00           N1+
HETATM    9  C6  UNL     1       0.800   0.116   0.443  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.520   0.915  -0.429  1.00  0.00           O  
HETATM   11  C7  UNL     1       2.769   0.294  -0.413  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.654   0.774  -1.536  1.00  0.00           C  
HETATM   13  O3  UNL     1       3.837   2.135  -1.403  1.00  0.00           O  
HETATM   14  C9  UNL     1       2.540  -1.184  -0.439  1.00  0.00           C  
HETATM   15  O4  UNL     1       3.181  -1.758   0.673  1.00  0.00           O  
HETATM   16  C10 UNL     1       1.039  -1.264  -0.131  1.00  0.00           C  
HETATM   17  O5  UNL     1       0.748  -2.278   0.747  1.00  0.00           O  
HETATM   18  C11 UNL     1      -1.567  -0.360   0.146  1.00  0.00           C  
HETATM   19  H1  UNL     1      -5.606   0.286  -0.592  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.999  -1.055   0.510  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.296   1.442   0.851  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.532   2.989   1.603  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.190   2.356   1.404  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.331   0.145   1.419  1.00  0.00           H  
HETATM   25  H7  UNL     1       3.261   0.616   0.539  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.651   0.291  -1.377  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.303   0.458  -2.527  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.836   2.343  -0.443  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.797  -1.677  -1.378  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.109  -1.388   0.767  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.545  -1.367  -1.117  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.420  -3.098   0.345  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.311  -1.320  -0.272  1.00  0.00           H  
CONECT    1    2   19   20
CONECT    2    3    3    4
CONECT    4    5    5   18
CONECT    5    6   21
CONECT    6    7    7   22
CONECT    7    8   23
CONECT    8    9   18   18
CONECT    9   10   16   24
CONECT   10   11
CONECT   11   12   14   25
CONECT   12   13   26   27
CONECT   13   28
CONECT   14   15   16   29
CONECT   15   30
CONECT   16   17   31
CONECT   17   32
CONECT   18   33
END

HMDB0000855
     RDKit          3D
Nicotinamide riboside
 33 34  0  0  0  0  0  0  0  0999 V2000
   -5.3008   -0.5595   -0.0748 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9507   -0.9690   -0.2096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6687   -2.1002   -0.7035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105   -0.0501    0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2450    1.1554    0.7610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592    2.0265    1.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9219    1.6407    1.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5833    0.4474    0.5408 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.7997    0.1162    0.4427 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5204    0.9145   -0.4286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7687    0.2943   -0.4129 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6540    0.7735   -1.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8368    2.1347   -1.4028 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5400   -1.1841   -0.4392 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1814   -1.7577    0.6725 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0387   -1.2644   -0.1306 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7482   -2.2785    0.7465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5674   -0.3599    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6060    0.2862   -0.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9988   -1.0552    0.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2958    1.4419    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5320    2.9892    1.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904    2.3556    1.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3311    0.1445    1.4193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2607    0.6163    0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512    0.2907   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3034    0.4575   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8356    2.3433   -0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7970   -1.6770   -1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091   -1.3881    0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5452   -1.3669   -1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198   -3.0975    0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3106   -1.3205   -0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  8 18  2  0
 18  4  1  0
 16  9  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  9 24  1  1
 11 25  1  1
 12 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  6
 15 30  1  0
 16 31  1  6
 17 32  1  0
 18 33  1  0
M  CHG  1   8   1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(beta-D-Ribofuranosyl)nicotinamide	ChEBI
beta-Nicotinamide D-riboside	ChEBI
Nicotinamide ribonucleoside	ChEBI
Nicotinamide ribose	ChEBI
Nicotinamide-beta-riboside	ChEBI
N-Ribosylnicotinamide	Kegg
1-(b-D-Ribofuranosyl)nicotinamide	Generator
1-(Β-D-ribofuranosyl)nicotinamide	Generator
b-Nicotinamide D-riboside	Generator
Β-nicotinamide D-riboside	Generator
Nicotinamide-b-riboside	Generator
Nicotinamide-β-riboside	Generator
1-b-D-Ribosyl-3-pyridinecarboxamide	HMDB
1-beta-D-Ribosyl-3-pyridinecarboxamide	HMDB
1-beta-delta-Ribosyl-3-pyridinecarboxamide	HMDB
3-(Aminocarbonyl)-1-beta-D-ribofuranosyl-pyridinium	HMDB
3-(Aminocarbonyl)-1-beta-delta-ribofuranosyl-pyridinium	HMDB
Ribosylnicotinamide	HMDB
SRT-647	HMDB
SRT 647	HMDB

Chemical Formula

C₁₁H₁₅N₂O₅

Average Molecular Weight

255.2472

Monoisotopic Molecular Weight

255.0980966

IUPAC Name

3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium

Traditional Name

3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1lambda5-pyridin-1-ylium

CAS Registry Number

1341-23-7

SMILES

NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C11H14N2O5/c12-10(17)6-2-1-3-13(4-6)11-9(16)8(15)7(5-14)18-11/h1-4,7-9,11,14-16H,5H2,(H-,12,17)/p+1/t7-,8-,9-,11-/m1/s1

InChI Key

JLEBZPBDRKPWTD-TURQNECASA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

Alternative Parents

Substituents

N-glycosyl compound
Pentose monosaccharide
Nicotinamide
Pyridine carboxylic acid or derivatives
Monosaccharide
Pyridine
Pyridinium
Vinylogous amide
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Carboxamide group
Primary carboxylic acid amide
Organoheterocyclic compound
Oxacycle
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Organic oxide
Organonitrogen compound
Organopnictogen compound
Alcohol
Organic nitrogen compound
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

N-glycosylnicotinamide (CHEBI:15927 )
pyridine nucleoside (CHEBI:15927 )

Ontology

Not Available

Placenta (HMDB: HMDB0000855)

Excreta

Biofluid or Excreta

Urine (PMID: 21389975)
Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0000855)

Source

Exogenous

Exogenous (HMDB: HMDB0000855)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Vegetable

Cabbage

Onion-family vegetable

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)

Cereal and cereal product

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0000855)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Nicotinate and Nicotinamide Metabolism (HMDB: HMDB0000855)
Nicotinate and Nicotinamide Metabolism (PathBank: SMP0121074)
NAD Salvage (PathBank: SMP0121298)
NAD Metabolism (PathBank: SMP0002338)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.45 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-6.1	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.39	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.83 m³·mol⁻¹	ChemAxon
Polarizability	24.83 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	158.671	31661259
DarkChem	[M-H]-	155.658	31661259
AllCCS	[M+H]+	156.031	32859911
AllCCS	[M-H]-	156.859	32859911
DeepCCS	[M+H]+	154.42	30932474
DeepCCS	[M-H]-	152.024	30932474
DeepCCS	[M-2H]-	186.768	30932474
DeepCCS	[M+Na]+	161.098	30932474
AllCCS	[M+H]+	156.0	32859911
AllCCS	[M+H-H2O]+	152.4	32859911
AllCCS	[M+NH4]+	159.4	32859911
AllCCS	[M+Na]+	160.3	32859911
AllCCS	[M-H]-	156.9	32859911
AllCCS	[M+Na-2H]-	156.5	32859911
AllCCS	[M+HCOO]-	156.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nicotinamide riboside	NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	3315.8	Standard polar	33892256
Nicotinamide riboside	NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2239.9	Standard non polar	33892256
Nicotinamide riboside	NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O	2591.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nicotinamide riboside,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O	2527.6	Semi standard non polar	33892256
Nicotinamide riboside,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	2508.7	Semi standard non polar	33892256
Nicotinamide riboside,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	2503.6	Semi standard non polar	33892256
Nicotinamide riboside,1TMS,isomer #4	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=C1	2510.7	Semi standard non polar	33892256
Nicotinamide riboside,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2525.8	Semi standard non polar	33892256
Nicotinamide riboside,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2512.8	Semi standard non polar	33892256
Nicotinamide riboside,2TMS,isomer #3	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O)=C1	2544.9	Semi standard non polar	33892256
Nicotinamide riboside,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C	2500.3	Semi standard non polar	33892256
Nicotinamide riboside,2TMS,isomer #5	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	2541.1	Semi standard non polar	33892256
Nicotinamide riboside,2TMS,isomer #6	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	2543.3	Semi standard non polar	33892256
Nicotinamide riboside,2TMS,isomer #7	C[Si](C)(C)N(C(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=C1)[Si](C)(C)C	2533.8	Semi standard non polar	33892256
Nicotinamide riboside,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2497.5	Semi standard non polar	33892256
Nicotinamide riboside,3TMS,isomer #2	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C)=C1	2551.2	Semi standard non polar	33892256
Nicotinamide riboside,3TMS,isomer #3	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O)=C1	2538.7	Semi standard non polar	33892256
Nicotinamide riboside,3TMS,isomer #4	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O	2542.5	Semi standard non polar	33892256
Nicotinamide riboside,3TMS,isomer #5	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	2540.8	Semi standard non polar	33892256
Nicotinamide riboside,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O	2519.8	Semi standard non polar	33892256
Nicotinamide riboside,3TMS,isomer #7	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C1	2528.5	Semi standard non polar	33892256
Nicotinamide riboside,4TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	2570.0	Semi standard non polar	33892256
Nicotinamide riboside,4TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	2604.8	Standard non polar	33892256
Nicotinamide riboside,4TMS,isomer #1	C[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=C1	2657.7	Standard polar	33892256
Nicotinamide riboside,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2556.6	Semi standard non polar	33892256
Nicotinamide riboside,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2623.4	Standard non polar	33892256
Nicotinamide riboside,4TMS,isomer #2	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2759.9	Standard polar	33892256
Nicotinamide riboside,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2547.1	Semi standard non polar	33892256
Nicotinamide riboside,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2614.2	Standard non polar	33892256
Nicotinamide riboside,4TMS,isomer #3	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2719.5	Standard polar	33892256
Nicotinamide riboside,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	2537.6	Semi standard non polar	33892256
Nicotinamide riboside,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	2611.6	Standard non polar	33892256
Nicotinamide riboside,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@@H]1O[Si](C)(C)C	2700.3	Standard polar	33892256
Nicotinamide riboside,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2582.7	Semi standard non polar	33892256
Nicotinamide riboside,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2648.5	Standard non polar	33892256
Nicotinamide riboside,5TMS,isomer #1	C[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2584.4	Standard polar	33892256
Nicotinamide riboside,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O	2772.2	Semi standard non polar	33892256
Nicotinamide riboside,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O	2758.2	Semi standard non polar	33892256
Nicotinamide riboside,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1[N+]1=CC=CC(C(N)=O)=C1	2740.9	Semi standard non polar	33892256
Nicotinamide riboside,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=C1	2774.5	Semi standard non polar	33892256
Nicotinamide riboside,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3001.7	Semi standard non polar	33892256
Nicotinamide riboside,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2996.9	Semi standard non polar	33892256
Nicotinamide riboside,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)=C1	3016.7	Semi standard non polar	33892256
Nicotinamide riboside,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	2976.4	Semi standard non polar	33892256
Nicotinamide riboside,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	3021.4	Semi standard non polar	33892256
Nicotinamide riboside,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3006.3	Semi standard non polar	33892256
Nicotinamide riboside,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=C1)[Si](C)(C)C(C)(C)C	3035.4	Semi standard non polar	33892256
Nicotinamide riboside,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(N)=O)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3211.0	Semi standard non polar	33892256
Nicotinamide riboside,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3252.7	Semi standard non polar	33892256
Nicotinamide riboside,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)=C1	3257.2	Semi standard non polar	33892256
Nicotinamide riboside,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O	3249.6	Semi standard non polar	33892256
Nicotinamide riboside,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3222.4	Semi standard non polar	33892256
Nicotinamide riboside,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O	3258.9	Semi standard non polar	33892256
Nicotinamide riboside,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1[N+]1=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3248.9	Semi standard non polar	33892256
Nicotinamide riboside,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3431.0	Semi standard non polar	33892256
Nicotinamide riboside,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3360.8	Standard non polar	33892256
Nicotinamide riboside,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C1=CC=C[N+]([C@@H]2O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)=C1	3098.5	Standard polar	33892256
Nicotinamide riboside,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3449.5	Semi standard non polar	33892256
Nicotinamide riboside,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3380.4	Standard non polar	33892256
Nicotinamide riboside,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3107.3	Standard polar	33892256
Nicotinamide riboside,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3450.9	Semi standard non polar	33892256
Nicotinamide riboside,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3368.7	Standard non polar	33892256
Nicotinamide riboside,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3075.7	Standard polar	33892256
Nicotinamide riboside,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3423.1	Semi standard non polar	33892256
Nicotinamide riboside,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3358.4	Standard non polar	33892256
Nicotinamide riboside,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3062.2	Standard polar	33892256
Nicotinamide riboside,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3587.2	Semi standard non polar	33892256
Nicotinamide riboside,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3532.1	Standard non polar	33892256
Nicotinamide riboside,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1O[C@@H]([N+]2=CC=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3065.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (Non-derivatized) - 70eV, Positive	splash10-070f-9530000000-71d9e02ee640bb800185	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (3 TMS) - 70eV, Positive	splash10-0a6r-9825400000-99de0fc632f408e32a12	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nicotinamide riboside GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 0V, positive-QTOF	splash10-0a4i-0190000000-51bf764225f08b566d36	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 1V, positive-QTOF	splash10-0a4i-0290000000-ffbe280293f874204044	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 2V, positive-QTOF	splash10-05fr-0970000000-1714e669425e34d3754a	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 3V, positive-QTOF	splash10-00di-0920000000-77ef12950b3152d752c8	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 5V, positive-QTOF	splash10-00di-0900000000-b14d15851532222ba74a	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 6V, positive-QTOF	splash10-00di-0900000000-277d95be8f0485eb3ce5	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 7V, positive-QTOF	splash10-00di-0900000000-354c1f3978635e5109bb	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 8V, positive-QTOF	splash10-00di-0900000000-ea5e376f71c6414964bc	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 10V, positive-QTOF	splash10-00di-0900000000-6b289ae1c5f53e92f774	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 11V, positive-QTOF	splash10-00di-1900000000-6ad92fa16e2cca17f959	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 12V, positive-QTOF	splash10-00di-1900000000-cee8757ed6b406ccf044	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 15V, positive-QTOF	splash10-00di-2900000000-78f21d967892a0d9ab85	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 19V, positive-QTOF	splash10-00di-3900000000-cd1f66bfc8ded7bd098e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 22V, positive-QTOF	splash10-00e9-8900000000-5a6bc8100043575c6a58	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 28V, positive-QTOF	splash10-00ai-9200000000-aedd3c5bf179b666a6ae	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 33V, positive-QTOF	splash10-003r-9000000000-22053c801abdfaf5f562	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside Orbitrap 41V, positive-QTOF	splash10-0fai-9000000000-b6b4b7e819e08c863a9a	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside n/a 17V, positive-QTOF	splash10-00di-0900000000-3364e345334aa7f5a742	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nicotinamide riboside n/a 17V, positive-QTOF	splash10-004i-9000000000-3bf262f96423e85a1756	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide riboside 10V, Positive-QTOF	splash10-0a4i-0090000000-e25d1beb47cb1fe9e4cb	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide riboside 20V, Positive-QTOF	splash10-002b-3090000000-03687e9ef697eda1d6c8	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide riboside 40V, Positive-QTOF	splash10-052g-9300000000-2755bde4df843d2227f2	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide riboside 10V, Negative-QTOF	splash10-0udi-0090000000-809be1146b2a2c8d96a7	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide riboside 20V, Negative-QTOF	splash10-0udi-1390000000-2fc72cf0619f182e044f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nicotinamide riboside 40V, Negative-QTOF	splash10-0k96-9300000000-4d5b96b192f3484b1b8a	2015-09-15	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Nicotinate and nicotinamide metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Autosomal dominant polycystic kidney disease (ADPKD)	21389975	details

Associated Disorders and Diseases

Disease References

Autosomal dominant polycystic kidney disease
Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]

Associated OMIM IDs

601313 (Autosomal dominant polycystic kidney disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022281

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Nicotinamide riboside

METLIN ID

5818

PubChem Compound

439924

PDB ID

Not Available

ChEBI ID

15927

Food Biomarker Ontology

Not Available

VMH ID

RNAM

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Franchetti, Palmarisa; Pasqualini, Michela; Petrelli, Riccardo; Ricciutelli, Massimo; Vita, Patrizia; Cappellacci, Loredana. Stereoselective synthesis of nicotinamide b-riboside and nucleoside analogs. Bioorganic & Medicinal Chemistry Letters (2004), 14(18), 4655-4658 Yang, T, Chan NY, Sauve AA. Syntheses of nicotinamide riboside and deriviatives.. J. Med Chem. 50:6458-61 (2007)..

Material Safety Data Sheet (MSDS)

Not Available

General References

Bieganowski P, Brenner C: Discoveries of nicotinamide riboside as a nutrient and conserved NRK genes establish a Preiss-Handler independent route to NAD+ in fungi and humans. Cell. 2004 May 14;117(4):495-502. [PubMed:15137942 ]
Wall KA, Klis M, Kornet J, Coyle D, Ame JC, Jacobson MK, Slama JT: Inhibition of the intrinsic NAD+ glycohydrolase activity of CD38 by carbocyclic NAD analogues. Biochem J. 1998 Nov 1;335 ( Pt 3):631-6. [PubMed:9794804 ]
Pankiewicz KW, Watanabe KA, Lesiak-Watanabe K, Goldstein BM, Jayaram HN: The chemistry of nicotinamide adenine dinucleotide (NAD) analogues containing C-nucleosides related to nicotinamide riboside. Curr Med Chem. 2002 Apr;9(7):733-41. [PubMed:11966436 ]
Magni G, Amici A, Emanuelli M, Orsomando G, Raffaelli N, Ruggieri S: Enzymology of NAD+ homeostasis in man. Cell Mol Life Sci. 2004 Jan;61(1):19-34. [PubMed:14704851 ]
Schalk-Hihi C, Zhang YZ, Markham GD: The conformation of NADH bound to inosine 5'-monophosphate dehydrogenase determined by transferred nuclear Overhauser effect spectroscopy. Biochemistry. 1998 May 19;37(20):7608-16. [PubMed:9585576 ]
Bogan KL, Brenner C: Nicotinic acid, nicotinamide, and nicotinamide riboside: a molecular evaluation of NAD+ precursor vitamins in human nutrition. Annu Rev Nutr. 2008;28:115-30. doi: 10.1146/annurev.nutr.28.061807.155443. [PubMed:18429699 ]
Belenky P, Racette FG, Bogan KL, McClure JM, Smith JS, Brenner C: Nicotinamide riboside promotes Sir2 silencing and extends lifespan via Nrk and Urh1/Pnp1/Meu1 pathways to NAD+. Cell. 2007 May 4;129(3):473-84. [PubMed:17482543 ]
Canto C, Houtkooper RH, Pirinen E, Youn DY, Oosterveer MH, Cen Y, Fernandez-Marcos PJ, Yamamoto H, Andreux PA, Cettour-Rose P, Gademann K, Rinsch C, Schoonjans K, Sauve AA, Auwerx J: The NAD(+) precursor nicotinamide riboside enhances oxidative metabolism and protects against high-fat diet-induced obesity. Cell Metab. 2012 Jun 6;15(6):838-47. doi: 10.1016/j.cmet.2012.04.022. [PubMed:22682224 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 5'-nucleotidase

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes extracellular nucleotides into membrane permeable nucleosides.
Gene Name:: NT5E
Uniprot ID:: P21589
Molecular weight:: 57948.125

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

2. Cytosolic 5'-nucleotidase 1B

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides. Helps to regulate adenosine levels (By similarity).
Gene Name:: NT5C1B
Uniprot ID:: Q96P26
Molecular weight:: 68803.055

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

3. Cytosolic 5'-nucleotidase 1A

General function:: Involved in nucleotide binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides and has a broad substrate specificity. Helps to regulate adenosine levels in heart during ischemia and hypoxia.
Gene Name:: NT5C1A
Uniprot ID:: Q9BXI3
Molecular weight:: 41020.145

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

4. 5'(3')-deoxyribonucleotidase, cytosolic type

General function:: Involved in metal ion binding
Specific function:: Dephosphorylates the 5' and 2'(3')-phosphates of deoxyribonucleotides, with a preference for dUMP and dTMP, intermediate activity towards dGMP, and low activity towards dCMP and dAMP.
Gene Name:: NT5C
Uniprot ID:: Q8TCD5
Molecular weight:: Not Available

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

5. 5'(3')-deoxyribonucleotidase, mitochondrial

General function:: Involved in phosphatase activity
Specific function:: Dephosphorylates specifically the 5' and 2'(3')-phosphates of uracil and thymine deoxyribonucleotides, and so protects mitochondrial DNA replication from excess dTTP. Has only marginal activity towards dIMP and dGMP.
Gene Name:: NT5M
Uniprot ID:: Q9NPB1
Molecular weight:: Not Available

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

6. Ribosyldihydronicotinamide dehydrogenase [quinone]

General function:: Involved in electron carrier activity
Specific function:: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:: NQO2
Uniprot ID:: P16083
Molecular weight:: 25918.4

Enzyme Details

7. Cytosolic 5'-nucleotidase 3

General function:: Involved in magnesium ion binding
Specific function:: Can act both as nucleotidase and as phosphotransferase.
Gene Name:: NT5C3
Uniprot ID:: Q9H0P0
Molecular weight:: 33914.91

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

8. Cytosolic purine 5'-nucleotidase

General function:: Involved in 5'-nucleotidase activity
Specific function:: May have a critical role in the maintenance of a constant composition of intracellular purine/pyrimidine nucleotides in cooperation with other nucleotidases. Preferentially hydrolyzes inosine 5'-monophosphate (IMP) and other purine nucleotides.
Gene Name:: NT5C2
Uniprot ID:: P49902
Molecular weight:: 64969.2

Reactions

Nicotinamide ribotide + Water → Nicotinamide riboside + Phosphate	details

Enzyme Details

9. Purine nucleoside phosphorylase

General function:: Involved in purine-nucleoside phosphorylase activity
Specific function:: The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:: PNP
Uniprot ID:: P00491
Molecular weight:: 32117.69

Reactions

Nicotinamide riboside + Phosphate → Niacinamide + Ribose 1-phosphate	details

Enzyme Details

10. Nicotinamide riboside kinase 1

General function:: Involved in ATP binding
Specific function:: Catalyzes the phosphorylation of nicotinamide riboside (NR) and nicotinic acid riboside (NaR) to form nicotinamide mononucleotide (NMN) and nicotinic acid mononucleotide (NaMN). The enzyme also phosphorylates the antitumor drugs tiazofurin and 3-deazaguanosine.
Gene Name:: NMRK1
Uniprot ID:: Q9NWW6
Molecular weight:: 20152.76

Reactions

Adenosine triphosphate + Nicotinamide riboside → ADP + Nicotinamide ribotide	details

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Nicotinamide riboside (HMDB0000855)

MOL for HMDB0000855 (Nicotinamide riboside)

3D MOL for HMDB0000855 (Nicotinamide riboside)

3D SDF for HMDB0000855 (Nicotinamide riboside)

3D-SDF for HMDB0000855 (Nicotinamide riboside)

PDB for HMDB0000855 (Nicotinamide riboside)

3D PDB for HMDB0000855 (Nicotinamide riboside)

SMILES for HMDB0000855 (Nicotinamide riboside)

INCHI for HMDB0000855 (Nicotinamide riboside)

Structure for HMDB0000855 (Nicotinamide riboside)

3D Structure for HMDB0000855 (Nicotinamide riboside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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