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Showing metabocard for 2-Methyl-1-hydroxypropyl-ThPP (HMDB0006866)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 17:09:17 UTC
Update Date2021-09-14 15:45:11 UTC
HMDB IDHMDB0006866
Secondary Accession Numbers
  • HMDB06866
Metabolite Identification
Common Name2-Methyl-1-hydroxypropyl-ThPP
Description2-Methyl-1-hydroxypropyl-ThPP is an intermediate in valine, leucine and isoleucine degradation(KEGG ID C15976). It is the second to last step in the synthesis of isobutyryl-CoA and is converted from 3-methyl-2-oxobutanoate via the enzyme 2-oxoisovalerate dehydrogenase [EC:1.2.4.4]. It is then converted to S-(2-methylpropanoyl)-dihydrolipoamide-E via the enzyme 2-oxoisovalerate dehydrogenase [EC:1.2.4.4]].
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006866 (2-Methyl-1-hydroxypropyl-ThPP)

 
  Mrv0541 02231220542D          
 
 31 32  0  0  0  0            999 V2000
   18.9913  -13.6159    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   19.3704  -12.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5736  -14.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2744  -13.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1836  -13.0162    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9981  -12.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3077  -13.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4805  -15.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5611  -13.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1781  -12.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4530  -11.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0417  -14.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5611  -14.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -13.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7344  -13.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -14.8738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2744  -14.8634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1275  -13.6194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4684  -14.1397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1275  -14.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1611  -13.6917    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.4141  -14.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8950  -14.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4127  -14.5187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5878  -13.6227    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.3184  -13.9985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8394  -14.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1611  -12.8659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5878  -12.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8059  -11.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7248  -12.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5  7  1  0  0  0  0
 18 20  1  0  0  0  0
 21 28  2  0  0  0  0
 25 29  2  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
M  CHG  1   1   1
M  END
Download

3D MOL for HMDB0006866 (2-Methyl-1-hydroxypropyl-ThPP)

HMDB0006866
     RDKit          3D
2-Methyl-1-hydroxypropyl-ThPP
 58 59  0  0  0  0  0  0  0  0999 V2000
   -4.4413    5.0091   -1.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8487    3.8104   -0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    3.6835    0.6519 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127    2.5934    1.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203    1.5688    0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0908    0.5559    1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1787   -0.4256    0.8666 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.4532   -1.7187    0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581   -2.4116    0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8195   -1.6159    1.1807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016   -3.0667   -0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127   -4.1195   -0.9169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4320   -3.3408   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0138   -2.4049    0.2073 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9921   -1.0444    0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3280   -0.7162   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4300   -0.4117    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3702    0.2569    0.0018 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8381   -0.3701   -0.1387 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.4825    0.2269   -1.4670 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7534   -2.0466   -0.5627 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9432   -0.0883    1.0474 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6856    1.4225    0.7155 P   0  0  0  0  0  5  0  0  0  0  0  0
    8.3867    1.9080    1.9244 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3584    2.4745    0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6596    1.2950   -0.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0595   -0.0670    0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5133    1.3833    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7221    1.7177   -0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2026    0.7073   -1.6130 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2825    2.8212   -1.3683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5561    5.8581   -0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4167    4.6722   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141    5.3989   -2.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3567    2.5104    2.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8409    0.1152    2.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310    1.2005    2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7221   -3.2605    1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5029   -1.5812    0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7407   -2.1966   -1.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7075   -4.7148   -0.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1512   -3.7633   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -4.8125   -1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9397   -2.3882   -1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4618   -4.0267   -1.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0108   -3.8021   -0.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424   -1.8309   -0.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5086   -0.2296   -1.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1728    0.1943    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9796   -1.2968    1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633   -2.6183    0.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3617    2.6298   -0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6449    0.4185   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736    2.0905    1.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800    1.5138    0.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224    1.7084   -0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    0.0390   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2072    0.5853   -1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 15 27  2  0
 27 28  1  0
  5 29  1  0
 29 30  1  0
 29 31  2  0
 31  2  1  0
 27  7  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  6 36  1  0
  6 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 21 51  1  0
 25 52  1  0
 26 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 30 57  1  0
 30 58  1  0
M  CHG  1   7   1
M  END
Download

3D SDF for HMDB0006866 (2-Methyl-1-hydroxypropyl-ThPP)

 
  Mrv0541 02231220542D          
 
 31 32  0  0  0  0            999 V2000
   18.9913  -13.6159    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   19.3704  -12.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5736  -14.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2744  -13.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1836  -13.0162    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9981  -12.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3077  -13.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4805  -15.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5611  -13.6194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1781  -12.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4530  -11.4552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0417  -14.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5611  -14.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -13.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7344  -13.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8374  -14.8738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2744  -14.8634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1275  -13.6194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4684  -14.1397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1275  -14.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1611  -13.6917    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.4141  -14.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8950  -14.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4127  -14.5187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5878  -13.6227    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.3184  -13.9985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8394  -14.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1611  -12.8659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5878  -12.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8059  -11.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7248  -12.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5  7  1  0  0  0  0
 18 20  1  0  0  0  0
 21 28  2  0  0  0  0
 25 29  2  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
M  CHG  1   1   1
M  END
> <DATABASE_ID>
HMDB0006866

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C(O)C1=[N+](CC2=C(N)N=C(C)N=C2)C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S1

> <INCHI_IDENTIFIER>
InChI=1S/C16H26N4O8P2S/c1-9(2)14(21)16-20(8-12-7-18-11(4)19-15(12)17)10(3)13(31-16)5-6-27-30(25,26)28-29(22,23)24/h7,9,14,21H,5-6,8H2,1-4H3,(H4-,17,18,19,22,23,24,25,26)/p+1

> <INCHI_KEY>
SSYCSHKTIOHFEZ-UHFFFAOYSA-O

> <FORMULA>
C16H27N4O8P2S

> <MOLECULAR_WEIGHT>
497.42

> <EXACT_MASS>
497.102482574

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
46.15230293114812

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-ium

> <ALOGPS_LOGP>
-0.43

> <JCHEM_LOGP>
-6.04769278226597

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.1978436606439984

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7783050504179663

> <JCHEM_PKA_STRONGEST_BASIC>
5.531111660504906

> <JCHEM_POLAR_SURFACE_AREA>
189.2

> <JCHEM_REFRACTIVITY>
125.57509999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-ium

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0006866 (2-Methyl-1-hydroxypropyl-ThPP)

HMDB0006866
     RDKit          3D
2-Methyl-1-hydroxypropyl-ThPP
 58 59  0  0  0  0  0  0  0  0999 V2000
   -4.4413    5.0091   -1.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8487    3.8104   -0.6536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8526    3.6835    0.6519 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3127    2.5934    1.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203    1.5688    0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0908    0.5559    1.3580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1787   -0.4256    0.8666 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.4532   -1.7187    0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581   -2.4116    0.8005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8195   -1.6159    1.1807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0016   -3.0667   -0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0127   -4.1195   -0.9169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4320   -3.3408   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0138   -2.4049    0.2073 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9921   -1.0444    0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3280   -0.7162   -0.1367 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4300   -0.4117    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3702    0.2569    0.0018 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8381   -0.3701   -0.1387 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.4825    0.2269   -1.4670 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7534   -2.0466   -0.5627 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9432   -0.0883    1.0474 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6856    1.4225    0.7155 P   0  0  0  0  0  5  0  0  0  0  0  0
    8.3867    1.9080    1.9244 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3584    2.4745    0.3986 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6596    1.2950   -0.6353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0595   -0.0670    0.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5133    1.3833    0.6038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7221    1.7177   -0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2026    0.7073   -1.6130 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2825    2.8212   -1.3683 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5561    5.8581   -0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4167    4.6722   -1.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9141    5.3989   -2.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3567    2.5104    2.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8409    0.1152    2.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310    1.2005    2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7221   -3.2605    1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5029   -1.5812    0.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7407   -2.1966   -1.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7075   -4.7148   -0.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1512   -3.7633   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5523   -4.8125   -1.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9397   -2.3882   -1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4618   -4.0267   -1.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0108   -3.8021   -0.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7424   -1.8309   -0.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5086   -0.2296   -1.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1728    0.1943    1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9796   -1.2968    1.2405 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633   -2.6183    0.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3617    2.6298   -0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6449    0.4185   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736    2.0905    1.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5800    1.5138    0.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224    1.7084   -0.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8750    0.0390   -2.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2072    0.5853   -1.8042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
  8 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 23 26  1  0
 15 27  2  0
 27 28  1  0
  5 29  1  0
 29 30  1  0
 29 31  2  0
 31  2  1  0
 27  7  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  6 36  1  0
  6 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 21 51  1  0
 25 52  1  0
 26 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 30 57  1  0
 30 58  1  0
M  CHG  1   7   1
M  END
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PDB for HMDB0006866 (2-Methyl-1-hydroxypropyl-ThPP)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      35.450 -25.416   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0      36.158 -24.046   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      36.537 -26.510   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      34.112 -24.651   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0      37.676 -24.297   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0      35.463 -22.670   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      37.908 -25.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      36.364 -28.035   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.781 -25.423   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.932 -22.580   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      36.312 -21.383   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      39.278 -26.523   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.781 -26.973   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.430 -24.657   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.571 -25.687   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      31.430 -27.764   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      34.112 -27.745   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      30.105 -25.423   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      41.941 -26.394   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      30.105 -26.973   0.000  0.00  0.00           C+0
HETATM   21  P   UNK     0      43.234 -25.558   0.000  0.00  0.00           P+0
HETATM   22  C   UNK     0      28.773 -27.745   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      44.604 -26.265   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      43.704 -27.102   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      45.897 -25.429   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      47.261 -26.131   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      46.367 -26.973   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      43.234 -24.016   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      45.897 -23.888   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      33.238 -21.195   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      33.086 -23.865   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2    7                                                       
CONECT    6    2   10   11                                                  
CONECT    7    3   12    5                                                  
CONECT    8    3                                                            
CONECT    9    4   13   14                                                  
CONECT   10    6   30   31                                                  
CONECT   11    6                                                            
CONECT   12    7   15                                                       
CONECT   13    9   16   17                                                  
CONECT   14    9   18                                                       
CONECT   15   12   19                                                       
CONECT   16   13   20                                                       
CONECT   17   13                                                            
CONECT   18   14   20                                                       
CONECT   19   15   21                                                       
CONECT   20   16   22   18                                                  
CONECT   21   19   23   24   28                                             
CONECT   22   20                                                            
CONECT   23   21   25                                                       
CONECT   24   21                                                            
CONECT   25   23   26   27   29                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   21                                                            
CONECT   29   25                                                            
CONECT   30   10                                                            
CONECT   31   10                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END
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3D PDB for HMDB0006866 (2-Methyl-1-hydroxypropyl-ThPP)

COMPND    HMDB0006866
HETATM    1  C1  UNL     1      -4.441   5.009  -1.327  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.849   3.810  -0.654  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.853   3.684   0.652  1.00  0.00           N  
HETATM    4  C3  UNL     1      -3.313   2.593   1.259  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.720   1.569   0.502  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.091   0.556   1.358  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.179  -0.426   0.867  1.00  0.00           N1+
HETATM    8  C6  UNL     1      -1.453  -1.719   0.689  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.758  -2.412   0.800  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.819  -1.616   1.181  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.002  -3.067  -0.549  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.013  -4.119  -0.917  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.432  -3.341  -0.859  1.00  0.00           C  
HETATM   14  S1  UNL     1       0.014  -2.405   0.207  1.00  0.00           S  
HETATM   15  C11 UNL     1       0.992  -1.044   0.217  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.328  -0.716  -0.137  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.430  -0.412   0.868  1.00  0.00           C  
HETATM   18  O2  UNL     1       4.370   0.257   0.002  1.00  0.00           O  
HETATM   19  P1  UNL     1       5.838  -0.370  -0.139  1.00  0.00           P  
HETATM   20  O3  UNL     1       6.482   0.227  -1.467  1.00  0.00           O  
HETATM   21  O4  UNL     1       5.753  -2.047  -0.563  1.00  0.00           O  
HETATM   22  O5  UNL     1       6.943  -0.088   1.047  1.00  0.00           O  
HETATM   23  P2  UNL     1       7.686   1.422   0.715  1.00  0.00           P  
HETATM   24  O6  UNL     1       8.387   1.908   1.924  1.00  0.00           O  
HETATM   25  O7  UNL     1       6.358   2.474   0.399  1.00  0.00           O  
HETATM   26  O8  UNL     1       8.660   1.295  -0.635  1.00  0.00           O  
HETATM   27  C14 UNL     1       0.060  -0.067   0.625  1.00  0.00           C  
HETATM   28  C15 UNL     1       0.513   1.383   0.604  1.00  0.00           C  
HETATM   29  C16 UNL     1      -2.722   1.718  -0.797  1.00  0.00           C  
HETATM   30  N3  UNL     1      -2.203   0.707  -1.613  1.00  0.00           N  
HETATM   31  N4  UNL     1      -3.283   2.821  -1.368  1.00  0.00           N  
HETATM   32  H1  UNL     1      -4.556   5.858  -0.595  1.00  0.00           H  
HETATM   33  H2  UNL     1      -5.417   4.672  -1.687  1.00  0.00           H  
HETATM   34  H3  UNL     1      -3.914   5.399  -2.169  1.00  0.00           H  
HETATM   35  H4  UNL     1      -3.357   2.510   2.330  1.00  0.00           H  
HETATM   36  H5  UNL     1      -2.841   0.115   2.025  1.00  0.00           H  
HETATM   37  H6  UNL     1      -1.531   1.200   2.155  1.00  0.00           H  
HETATM   38  H7  UNL     1      -2.722  -3.260   1.545  1.00  0.00           H  
HETATM   39  H8  UNL     1      -4.503  -1.581   0.475  1.00  0.00           H  
HETATM   40  H9  UNL     1      -2.741  -2.197  -1.282  1.00  0.00           H  
HETATM   41  H10 UNL     1      -1.707  -4.715  -0.072  1.00  0.00           H  
HETATM   42  H11 UNL     1      -1.151  -3.763  -1.520  1.00  0.00           H  
HETATM   43  H12 UNL     1      -2.552  -4.812  -1.646  1.00  0.00           H  
HETATM   44  H13 UNL     1      -4.940  -2.388  -1.241  1.00  0.00           H  
HETATM   45  H14 UNL     1      -4.462  -4.027  -1.726  1.00  0.00           H  
HETATM   46  H15 UNL     1      -5.011  -3.802  -0.045  1.00  0.00           H  
HETATM   47  H16 UNL     1       2.742  -1.831  -0.493  1.00  0.00           H  
HETATM   48  H17 UNL     1       2.509  -0.230  -1.171  1.00  0.00           H  
HETATM   49  H18 UNL     1       3.173   0.194   1.693  1.00  0.00           H  
HETATM   50  H19 UNL     1       3.980  -1.297   1.241  1.00  0.00           H  
HETATM   51  H20 UNL     1       5.563  -2.618   0.219  1.00  0.00           H  
HETATM   52  H21 UNL     1       6.362   2.630  -0.564  1.00  0.00           H  
HETATM   53  H22 UNL     1       8.645   0.419  -1.088  1.00  0.00           H  
HETATM   54  H23 UNL     1      -0.074   2.090   1.214  1.00  0.00           H  
HETATM   55  H24 UNL     1       1.580   1.514   0.687  1.00  0.00           H  
HETATM   56  H25 UNL     1       0.322   1.708  -0.502  1.00  0.00           H  
HETATM   57  H26 UNL     1      -2.875   0.039  -2.086  1.00  0.00           H  
HETATM   58  H27 UNL     1      -1.207   0.585  -1.804  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    3   31
CONECT    3    4
CONECT    4    5    5   35
CONECT    5    6   29
CONECT    6    7   36   37
CONECT    7    8    8   27
CONECT    8    9   14
CONECT    9   10   11   38
CONECT   10   39
CONECT   11   12   13   40
CONECT   12   41   42   43
CONECT   13   44   45   46
CONECT   14   15
CONECT   15   16   27   27
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19
CONECT   19   20   20   21   22
CONECT   21   51
CONECT   22   23
CONECT   23   24   24   25   26
CONECT   25   52
CONECT   26   53
CONECT   27   28
CONECT   28   54   55   56
CONECT   29   30   31   31
CONECT   30   57   58
END
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SMILES for HMDB0006866 (2-Methyl-1-hydroxypropyl-ThPP)

CC(C)C(O)C1=[N+](CC2=C(N)N=C(C)N=C2)C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S1
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INCHI for HMDB0006866 (2-Methyl-1-hydroxypropyl-ThPP)

InChI=1S/C16H26N4O8P2S/c1-9(2)14(21)16-20(8-12-7-18-11(4)19-15(12)17)10(3)13(31-16)5-6-27-30(25,26)28-29(22,23)24/h7,9,14,21H,5-6,8H2,1-4H3,(H4-,17,18,19,22,23,24,25,26)/p+1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-Hydroxy-2-methylpropyl-thiamine diphosphateChEBI
1-Hydroxy-2-methylpropyl-thiamine pyrophosphateChEBI
2-Methyl-1-hydroxypropyl-thiamine diphosphateChEBI
2-Methyl-1-hydroxypropyl-thiamine pyrophosphateChEBI
2-Methyl-1-hydroxypropyl-TPPChEBI
3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-5-(2-diphosphoethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-iumChEBI
1-Hydroxy-2-methylpropyl-thiamine diphosphoric acidGenerator
1-Hydroxy-2-methylpropyl-thiamine pyrophosphoric acidGenerator
2-Methyl-1-hydroxypropyl-thiamine diphosphoric acidGenerator
2-Methyl-1-hydroxypropyl-thiamine pyrophosphoric acidGenerator
2-Methyl-1-hydroxypropyl-THPPChEBI
Chemical FormulaC16H27N4O8P2S
Average Molecular Weight497.42
Monoisotopic Molecular Weight497.102482574
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-ium
Traditional Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-ium
CAS Registry NumberNot Available
SMILES
CC(C)C(O)C1=[N+](CC2=C(N)N=C(C)N=C2)C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S1
InChI Identifier
InChI=1S/C16H26N4O8P2S/c1-9(2)14(21)16-20(8-12-7-18-11(4)19-15(12)17)10(3)13(31-16)5-6-27-30(25,26)28-29(22,23)24/h7,9,14,21H,5-6,8H2,1-4H3,(H4-,17,18,19,22,23,24,25,26)/p+1
InChI KeySSYCSHKTIOHFEZ-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentThiamine phosphates
Alternative Parents
Substituents
  • Thiamine-phosphate
  • Organic pyrophosphate
  • 2,4,5-trisubstituted 1,3-thiazole
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Imidolactam
  • Heteroaromatic compound
  • Azole
  • Thiazole
  • Secondary alcohol
  • Azacycle
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Primary amine
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic alcohol
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024122
KNApSAcK IDNot Available
Chemspider ID26333171
KEGG Compound IDC15976
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23724626
PDB IDNot Available
ChEBI ID48522
Food Biomarker OntologyNot Available
VMH ID2M1HPTPP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
General function:
Involved in catalytic activity
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHB
Uniprot ID:
P21953
Molecular weight:
43122.065
Reactions
alpha-Ketoisovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxidedetails
2-Methyl-1-hydroxypropyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + Thiamine pyrophosphatedetails
Enzyme Details
2. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHA
Uniprot ID:
P12694
Molecular weight:
50470.58
Reactions
alpha-Ketoisovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxidedetails
2-Methyl-1-hydroxypropyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + Thiamine pyrophosphatedetails