Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-21 06:25:53 UTC

Update Date

2022-03-07 03:17:54 UTC

HMDB ID

HMDB0062447

Secondary Accession Numbers

HMDB62447

Metabolite Identification

Common Name

anhydroretinol

Description

anhydroretinol, also known as anhydrovitamin a, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. anhydroretinol is possibly neutral.

Structure

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

HMDB0062447
     RDKit          3D
anhydroretinol
 48 48  0  0  0  0  0  0  0  0999 V2000
    7.9313   -0.6861    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7029   -0.7928    1.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5595   -0.4206    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7768    0.1110   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3129   -0.5561    0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1960   -0.1724   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9455   -0.2822    0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    0.1043   -0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0370    0.6273   -1.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -0.0046   -0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5631    0.3667   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129    0.2505   -0.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9275    0.6552   -1.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7005    0.7271   -2.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221    0.9549   -0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3240    0.8737    0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930   -0.3545    1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949   -0.2810    0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6168   -1.7331    1.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254    0.6100    1.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7110   -0.9979    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2482   -0.3214   -0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4523   -1.1879    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7966    0.0410   -1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1687   -0.4823   -1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4303    1.1659   -1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1774   -0.9442    1.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4347    0.2216   -1.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7982   -0.6774    1.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6515    1.6851   -1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.0423   -2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062    0.4959   -2.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5347   -0.3951    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4554    0.7725   -1.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6067    0.6034   -3.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925    1.7497   -3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881   -0.0714   -3.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9625    1.2554   -1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3833    0.7154    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8758    1.7523    1.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494   -1.2779    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8290   -0.4526    2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4986   -2.4425    1.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0838   -1.9713    0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -1.9067    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    0.0698    2.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3808    1.1302    2.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9300    1.4308    1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
M  END

  Mrv0541 05041400022D          

 25 25  0  0  0  0            999 V2000
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  2  0  0  0  0
 10  8  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 16  2  1  0  0  0  0
 16  7  1  0  0  0  0
 16 10  2  0  0  0  0
 17  3  1  0  0  0  0
 17 11  1  0  0  0  0
 17 13  2  0  0  0  0
 18  4  1  0  0  0  0
 18 12  2  0  0  0  0
 19 14  2  0  0  0  0
 19 18  1  0  0  0  0
 20  5  1  0  0  0  0
 20  6  1  0  0  0  0
 20 15  1  0  0  0  0
 20 19  1  0  0  0  0
 21  8  1  0  0  0  0
 22 10  1  0  0  0  0
 23 11  1  0  0  0  0
 24 13  1  0  0  0  0
 25 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0062447

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]/C(=C(/[H])\C(\C)=C(/[H])\C(\[H])=C1\C(C)=CCCC1(C)C)/C(/[H])=C(\C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28/c1-7-16(2)10-8-11-17(3)13-14-19-18(4)12-9-15-20(19,5)6/h7-8,10-14H,1,9,15H2,2-6H3/b11-8+,16-10+,17-13+,19-14-

> <INCHI_KEY>
FWNRILWHNGFAIN-OYUWDNMLSA-N

> <FORMULA>
C20H28

> <MOLECULAR_WEIGHT>
268.4363

> <EXACT_MASS>
268.219100896

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
34.87919505022553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6E)-6-[(2E,4E,6E)-3,7-dimethylnona-2,4,6,8-tetraen-1-ylidene]-1,5,5-trimethylcyclohex-1-ene

> <ALOGPS_LOGP>
6.81

> <JCHEM_LOGP>
5.670876343333333

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
96.1928

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6E)-6-[(2E,4E,6E)-3,7-dimethylnona-2,4,6,8-tetraen-1-ylidene]-1,5,5-trimethylcyclohex-1-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0062447
     RDKit          3D
anhydroretinol
 48 48  0  0  0  0  0  0  0  0999 V2000
    7.9313   -0.6861    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7029   -0.7928    1.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5595   -0.4206    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7768    0.1110   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3129   -0.5561    0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1960   -0.1724   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9455   -0.2822    0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    0.1043   -0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0370    0.6273   -1.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -0.0046   -0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5631    0.3667   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129    0.2505   -0.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9275    0.6552   -1.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7005    0.7271   -2.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221    0.9549   -0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3240    0.8737    0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930   -0.3545    1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949   -0.2810    0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6168   -1.7331    1.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254    0.6100    1.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7110   -0.9979    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2482   -0.3214   -0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4523   -1.1879    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7966    0.0410   -1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1687   -0.4823   -1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4303    1.1659   -1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1774   -0.9442    1.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4347    0.2216   -1.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7982   -0.6774    1.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6515    1.6851   -1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.0423   -2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062    0.4959   -2.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5347   -0.3951    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4554    0.7725   -1.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6067    0.6034   -3.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925    1.7497   -3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881   -0.0714   -3.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9625    1.2554   -1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3833    0.7154    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8758    1.7523    1.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494   -1.2779    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8290   -0.4526    2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4986   -2.4425    1.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0838   -1.9713    0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -1.9067    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    0.0698    2.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3808    1.1302    2.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9300    1.4308    1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
M  END

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   20                                                            
CONECT    6   20                                                            
CONECT    7    1   16                                                       
CONECT    8   10   11   21                                                  
CONECT    9   12   15                                                       
CONECT   10    8   16   22                                                  
CONECT   11    8   17   23                                                  
CONECT   12    9   18                                                       
CONECT   13   14   17   24                                                  
CONECT   14   13   19   25                                                  
CONECT   15    9   20                                                       
CONECT   16    2    7   10                                                  
CONECT   17    3   11   13                                                  
CONECT   18    4   12   19                                                  
CONECT   19   14   18   20                                                  
CONECT   20    5    6   15   19                                             
CONECT   21    8                                                            
CONECT   22   10                                                            
CONECT   23   11                                                            
CONECT   24   13                                                            
CONECT   25   14                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0062447
HETATM    1  C1  UNL     1       7.931  -0.686   0.778  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.703  -0.793   1.165  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.560  -0.421   0.350  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.777   0.111  -1.019  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.313  -0.556   0.817  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.196  -0.172  -0.026  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.945  -0.282   0.374  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.851   0.104  -0.480  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.037   0.627  -1.835  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.428  -0.005  -0.071  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.563   0.367  -0.880  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.813   0.250  -0.460  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.927   0.655  -1.353  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.701   0.727  -2.815  1.00  0.00           C  
HETATM   15  C15 UNL     1      -5.122   0.955  -0.882  1.00  0.00           C  
HETATM   16  C16 UNL     1      -5.324   0.874   0.593  1.00  0.00           C  
HETATM   17  C17 UNL     1      -4.593  -0.354   1.088  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.095  -0.281   0.888  1.00  0.00           C  
HETATM   19  C19 UNL     1      -2.617  -1.733   1.038  1.00  0.00           C  
HETATM   20  C20 UNL     1      -2.525   0.610   1.968  1.00  0.00           C  
HETATM   21  H1  UNL     1       8.711  -0.998   1.477  1.00  0.00           H  
HETATM   22  H2  UNL     1       8.248  -0.321  -0.156  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.452  -1.188   2.173  1.00  0.00           H  
HETATM   24  H4  UNL     1       6.797   0.041  -1.355  1.00  0.00           H  
HETATM   25  H5  UNL     1       5.169  -0.482  -1.761  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.430   1.166  -1.087  1.00  0.00           H  
HETATM   27  H7  UNL     1       4.177  -0.944   1.801  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.435   0.222  -1.018  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.798  -0.677   1.375  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.651   1.685  -1.933  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.317   0.042  -2.490  1.00  0.00           H  
HETATM   32  H12 UNL     1       2.006   0.496  -2.299  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.535  -0.395   0.925  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.455   0.772  -1.898  1.00  0.00           H  
HETATM   35  H15 UNL     1      -4.607   0.603  -3.405  1.00  0.00           H  
HETATM   36  H16 UNL     1      -3.292   1.750  -3.042  1.00  0.00           H  
HETATM   37  H17 UNL     1      -2.988  -0.071  -3.139  1.00  0.00           H  
HETATM   38  H18 UNL     1      -5.962   1.255  -1.487  1.00  0.00           H  
HETATM   39  H19 UNL     1      -6.383   0.715   0.784  1.00  0.00           H  
HETATM   40  H20 UNL     1      -4.876   1.752   1.060  1.00  0.00           H  
HETATM   41  H21 UNL     1      -4.949  -1.278   0.601  1.00  0.00           H  
HETATM   42  H22 UNL     1      -4.829  -0.453   2.169  1.00  0.00           H  
HETATM   43  H23 UNL     1      -3.499  -2.442   1.033  1.00  0.00           H  
HETATM   44  H24 UNL     1      -2.084  -1.971   0.086  1.00  0.00           H  
HETATM   45  H25 UNL     1      -2.045  -1.907   1.948  1.00  0.00           H  
HETATM   46  H26 UNL     1      -1.981   0.070   2.754  1.00  0.00           H  
HETATM   47  H27 UNL     1      -3.381   1.130   2.469  1.00  0.00           H  
HETATM   48  H28 UNL     1      -1.930   1.431   1.509  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3   23
CONECT    3    4    5    5
CONECT    4   24   25   26
CONECT    5    6   27
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9   10   10
CONECT    9   30   31   32
CONECT   10   11   33
CONECT   11   12   12   34
CONECT   12   13   18
CONECT   13   14   15   15
CONECT   14   35   36   37
CONECT   15   16   38
CONECT   16   17   39   40
CONECT   17   18   41   42
CONECT   18   19   20
CONECT   19   43   44   45
CONECT   20   46   47   48
END

HMDB0062447
     RDKit          3D
anhydroretinol
 48 48  0  0  0  0  0  0  0  0999 V2000
    7.9313   -0.6861    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7029   -0.7928    1.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5595   -0.4206    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7768    0.1110   -1.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3129   -0.5561    0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1960   -0.1724   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9455   -0.2822    0.3738 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8511    0.1043   -0.4804 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0370    0.6273   -1.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -0.0046   -0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5631    0.3667   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129    0.2505   -0.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9275    0.6552   -1.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7005    0.7271   -2.8154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1221    0.9549   -0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3240    0.8737    0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5930   -0.3545    1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949   -0.2810    0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6168   -1.7331    1.0377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5254    0.6100    1.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7110   -0.9979    1.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2482   -0.3214   -0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4523   -1.1879    2.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7966    0.0410   -1.3554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1687   -0.4823   -1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4303    1.1659   -1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1774   -0.9442    1.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4347    0.2216   -1.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7982   -0.6774    1.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6515    1.6851   -1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3173    0.0423   -2.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062    0.4959   -2.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5347   -0.3951    0.9245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4554    0.7725   -1.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6067    0.6034   -3.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925    1.7497   -3.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9881   -0.0714   -3.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9625    1.2554   -1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3833    0.7154    0.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8758    1.7523    1.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494   -1.2779    0.6014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8290   -0.4526    2.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4986   -2.4425    1.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0838   -1.9713    0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0454   -1.9067    1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810    0.0698    2.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3808    1.1302    2.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9300    1.4308    1.5088 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 12  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Anhydrovitamin a	HMDB
trans-Anhydrovitamin a	HMDB
Anhydroretinol	MeSH

Chemical Formula

C₂₀H₂₈

Average Molecular Weight

268.4363

Monoisotopic Molecular Weight

268.219100896

IUPAC Name

(6E)-6-[(2E,4E,6E)-3,7-dimethylnona-2,4,6,8-tetraen-1-ylidene]-1,5,5-trimethylcyclohex-1-ene

Traditional Name

(6E)-6-[(2E,4E,6E)-3,7-dimethylnona-2,4,6,8-tetraen-1-ylidene]-1,5,5-trimethylcyclohex-1-ene

CAS Registry Number

Not Available

SMILES

[H]/C(=C(/[H])\C(\C)=C(/[H])\C(\[H])=C1\C(C)=CCCC1(C)C)/C(/[H])=C(\C)C=C

InChI Identifier

InChI=1S/C20H28/c1-7-16(2)10-8-11-17(3)13-14-19-18(4)12-9-15-20(19,5)6/h7-8,10-14H,1,9,15H2,2-6H3/b11-8+,16-10+,17-13+,19-14-

InChI Key

FWNRILWHNGFAIN-OYUWDNMLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cyclofarsesane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
Cycloalkene
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0062447)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0022 g/l	ALOGPS
LogP	6.81	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.81	ALOGPS
logP	5.67	ChemAxon
logS	-5.1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	96.19 m³·mol⁻¹	ChemAxon
Polarizability	34.88 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	168.712	31661259
DarkChem	[M-H]-	169.373	31661259
DeepCCS	[M+H]+	195.348	30932474
DeepCCS	[M-H]-	192.953	30932474
DeepCCS	[M-2H]-	225.837	30932474
DeepCCS	[M+Na]+	201.261	30932474
AllCCS	[M+H]+	168.4	32859911
AllCCS	[M+H-H2O]+	165.0	32859911
AllCCS	[M+NH4]+	171.6	32859911
AllCCS	[M+Na]+	172.5	32859911
AllCCS	[M-H]-	172.7	32859911
AllCCS	[M+Na-2H]-	172.8	32859911
AllCCS	[M+HCOO]-	173.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
anhydroretinol	[H]/C(=C(/[H])\C(\C)=C(/[H])\C(\[H])=C1\C(C)=CCCC1(C)C)/C(/[H])=C(\C)C=C	2714.6	Standard polar	33892256
anhydroretinol	[H]/C(=C(/[H])\C(\C)=C(/[H])\C(\[H])=C1\C(C)=CCCC1(C)C)/C(/[H])=C(\C)C=C	2091.0	Standard non polar	33892256
anhydroretinol	[H]/C(=C(/[H])\C(\C)=C(/[H])\C(\[H])=C1\C(C)=CCCC1(C)C)/C(/[H])=C(\C)C=C	2025.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - anhydroretinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1290000000-016a94e4ec3a2dd2b25e	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - anhydroretinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - anhydroretinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 10V, Positive-QTOF	splash10-014i-2490000000-ceaf9937108ecbc219e9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 20V, Positive-QTOF	splash10-0fui-6950000000-7c7c89a4d9feac59ae37	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 40V, Positive-QTOF	splash10-0udi-9330000000-0f553bc1b3f267fd8fe4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 10V, Negative-QTOF	splash10-014i-0090000000-9f98354a74dce8944e36	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 20V, Negative-QTOF	splash10-014i-0090000000-9499b10eec769375f21d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 40V, Negative-QTOF	splash10-0gbi-3980000000-39b950dafd407ad8e8da	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 10V, Negative-QTOF	splash10-014i-0490000000-192dc77c2569dcb54a8b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 20V, Negative-QTOF	splash10-014s-0950000000-42254474be47a902838c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 40V, Negative-QTOF	splash10-066r-4920000000-0f01aa95711ffe9127fe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 10V, Positive-QTOF	splash10-01b9-6960000000-08df1cff099abca5c75b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 20V, Positive-QTOF	splash10-009l-9730000000-f597d278a45f1426e712	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - anhydroretinol 40V, Positive-QTOF	splash10-0fa9-9800000000-3d04abe1abfd3c3531f8	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02914

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5287678

PDB ID

ANR

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

CE5014

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for anhydroretinol (HMDB0062447)

MOL for HMDB0062447 (anhydroretinol)

3D MOL for HMDB0062447 (anhydroretinol)

3D SDF for HMDB0062447 (anhydroretinol)

3D-SDF for HMDB0062447 (anhydroretinol)

PDB for HMDB0062447 (anhydroretinol)

3D PDB for HMDB0062447 (anhydroretinol)

SMILES for HMDB0062447 (anhydroretinol)

INCHI for HMDB0062447 (anhydroretinol)

Structure for HMDB0062447 (anhydroretinol)

3D Structure for HMDB0062447 (anhydroretinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra