You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

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

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
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
Data?1582752411
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)

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)
https://cactus.nci.nih.gov/chemical/structure/CC(C)C(O)C1=%5BN+%5D(CC2=C(N)N=...
 OpenBabel09142113223D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:57})
 58 59  0  0  0  0  0  0  0  0999 V2000
    6.1121    3.3516    1.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7787    3.1144    0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0017    3.1123   -1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2028    1.7644    0.8966 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9945    1.7663    2.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8894    1.5308    0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7132    0.7183   -0.7912 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.8183   -0.0758   -1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9548   -1.3522   -0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0118   -2.2324   -0.7840 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9579   -1.9481   -1.7553 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0960   -3.3478   -0.0647 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1983   -3.6210    0.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3287   -4.8954    1.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -2.8107    1.1104 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0407   -1.6778    0.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    0.6331   -1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1483   -0.2748   -2.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958    1.4175   -0.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643    1.5255   -1.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6642    0.5011   -0.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0486    0.6034   -0.5793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1844   -0.3269    0.0815 P   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9391   -1.8593   -0.3468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1215   -0.2105    1.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6340    0.1487   -0.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1355   -0.0516    0.1124 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1177    0.9893   -0.6252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6210   -1.5560   -0.1925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1665    0.1905    1.5722 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4155    2.2986    0.5973 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.5223    4.3133    0.8678 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9532    3.3530    2.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8108    2.5574    0.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0800    3.9085    0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4119    4.0741   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7004    2.3182   -1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0517    2.9433   -1.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9016    0.9703    0.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3821    2.4491    2.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158   -0.3144   -2.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7443    0.4951   -1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9318   -1.0993   -2.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6465   -2.5978   -1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9296   -4.7091    2.5439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3386   -5.2419    1.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8122   -5.6568    1.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2104   -1.0210    0.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9464   -1.2777   -2.0646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636    0.1072   -2.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9834   -0.3105   -3.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2217    2.5290   -0.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    1.3298   -2.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3069   -0.5025   -0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    0.6968    0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9667   -2.0101   -1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0409    0.9250   -0.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6258   -1.7849   -1.1320 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2 35  1  0  0  0  0
  3 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 39  1  6  0  0  0
  5 40  1  0  0  0  0
  6  7  2  0  0  0  0
  6 31  1  0  0  0  0
  7  8  1  0  0  0  0
  7 17  1  0  0  0  0
  8  9  1  0  0  0  0
  8 41  1  0  0  0  0
  8 42  1  0  0  0  0
  9 10  2  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 43  1  0  0  0  0
 11 44  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 45  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
 15 16  2  0  0  0  0
 16 48  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
 19 20  1  0  0  0  0
 19 31  1  0  0  0  0
 20 21  1  0  0  0  0
 20 52  1  0  0  0  0
 20 53  1  0  0  0  0
 21 22  1  0  0  0  0
 21 54  1  0  0  0  0
 21 55  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  1  0  0  0
 23 26  1  0  0  0  0
 24 56  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  2  0  0  0  0
 28 57  1  0  0  0  0
 29 58  1  0  0  0  0
M  CHG  1   7   1
M  END
$$$$

Download
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

Download
3D PDB for HMDB0006866 (2-Methyl-1-hydroxypropyl-ThPP)
COMPND    https://cactus.nci.nih.gov/chemical/structure/CC(C)C(O)C1=%5BN+%5D(CC2=C(N)N=... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1       6.112   3.352   1.176  1.00  0.00           C  
HETATM    2  C   UNL     1       4.779   3.114   0.464  1.00  0.00           C  
HETATM    3  C   UNL     1       5.002   3.112  -1.050  1.00  0.00           C  
HETATM    4  C   UNL     1       4.203   1.764   0.897  1.00  0.00           C  
HETATM    5  O   UNL     1       3.994   1.766   2.310  1.00  0.00           O  
HETATM    6  C   UNL     1       2.889   1.531   0.196  1.00  0.00           C  
HETATM    7  N   UNL     1       2.713   0.718  -0.791  1.00  0.00           N1+
HETATM    8  C   UNL     1       3.818  -0.076  -1.334  1.00  0.00           C  
HETATM    9  C   UNL     1       3.955  -1.352  -0.544  1.00  0.00           C  
HETATM   10  C   UNL     1       5.012  -2.232  -0.784  1.00  0.00           C  
HETATM   11  N   UNL     1       5.958  -1.948  -1.755  1.00  0.00           N  
HETATM   12  N   UNL     1       5.096  -3.348  -0.065  1.00  0.00           N  
HETATM   13  C   UNL     1       4.198  -3.621   0.860  1.00  0.00           C  
HETATM   14  C   UNL     1       4.329  -4.895   1.654  1.00  0.00           C  
HETATM   15  N   UNL     1       3.189  -2.811   1.110  1.00  0.00           N  
HETATM   16  C   UNL     1       3.041  -1.678   0.439  1.00  0.00           C  
HETATM   17  C   UNL     1       1.496   0.633  -1.289  1.00  0.00           C  
HETATM   18  C   UNL     1       1.148  -0.275  -2.441  1.00  0.00           C  
HETATM   19  C   UNL     1       0.596   1.417  -0.690  1.00  0.00           C  
HETATM   20  C   UNL     1      -0.864   1.526  -1.047  1.00  0.00           C  
HETATM   21  C   UNL     1      -1.664   0.501  -0.240  1.00  0.00           C  
HETATM   22  O   UNL     1      -3.049   0.603  -0.579  1.00  0.00           O  
HETATM   23  P   UNL     1      -4.184  -0.327   0.082  1.00  0.00           P  
HETATM   24  O   UNL     1      -3.939  -1.859  -0.347  1.00  0.00           O  
HETATM   25  O   UNL     1      -4.122  -0.210   1.556  1.00  0.00           O  
HETATM   26  O   UNL     1      -5.634   0.149  -0.433  1.00  0.00           O  
HETATM   27  P   UNL     1      -7.136  -0.052   0.112  1.00  0.00           P  
HETATM   28  O   UNL     1      -8.118   0.989  -0.625  1.00  0.00           O  
HETATM   29  O   UNL     1      -7.621  -1.556  -0.193  1.00  0.00           O  
HETATM   30  O   UNL     1      -7.167   0.191   1.572  1.00  0.00           O  
HETATM   31  S   UNL     1       1.415   2.299   0.597  1.00  0.00           S  
HETATM   32  H   UNL     1       6.522   4.313   0.868  1.00  0.00           H  
HETATM   33  H   UNL     1       5.953   3.353   2.254  1.00  0.00           H  
HETATM   34  H   UNL     1       6.811   2.557   0.913  1.00  0.00           H  
HETATM   35  H   UNL     1       4.080   3.909   0.727  1.00  0.00           H  
HETATM   36  H   UNL     1       5.412   4.074  -1.358  1.00  0.00           H  
HETATM   37  H   UNL     1       5.700   2.318  -1.313  1.00  0.00           H  
HETATM   38  H   UNL     1       4.052   2.943  -1.557  1.00  0.00           H  
HETATM   39  H   UNL     1       4.902   0.970   0.633  1.00  0.00           H  
HETATM   40  H   UNL     1       3.382   2.449   2.617  1.00  0.00           H  
HETATM   41  H   UNL     1       3.616  -0.314  -2.378  1.00  0.00           H  
HETATM   42  H   UNL     1       4.744   0.495  -1.264  1.00  0.00           H  
HETATM   43  H   UNL     1       5.932  -1.099  -2.224  1.00  0.00           H  
HETATM   44  H   UNL     1       6.646  -2.598  -1.966  1.00  0.00           H  
HETATM   45  H   UNL     1       4.930  -4.709   2.544  1.00  0.00           H  
HETATM   46  H   UNL     1       3.339  -5.242   1.950  1.00  0.00           H  
HETATM   47  H   UNL     1       4.812  -5.657   1.042  1.00  0.00           H  
HETATM   48  H   UNL     1       2.210  -1.021   0.652  1.00  0.00           H  
HETATM   49  H   UNL     1       0.946  -1.278  -2.065  1.00  0.00           H  
HETATM   50  H   UNL     1       0.264   0.107  -2.950  1.00  0.00           H  
HETATM   51  H   UNL     1       1.983  -0.310  -3.140  1.00  0.00           H  
HETATM   52  H   UNL     1      -1.222   2.529  -0.817  1.00  0.00           H  
HETATM   53  H   UNL     1      -0.993   1.330  -2.112  1.00  0.00           H  
HETATM   54  H   UNL     1      -1.307  -0.502  -0.471  1.00  0.00           H  
HETATM   55  H   UNL     1      -1.536   0.697   0.824  1.00  0.00           H  
HETATM   56  H   UNL     1      -3.967  -2.010  -1.302  1.00  0.00           H  
HETATM   57  H   UNL     1      -9.041   0.925  -0.345  1.00  0.00           H  
HETATM   58  H   UNL     1      -7.626  -1.785  -1.132  1.00  0.00           H  
CONECT    1    2   32   33   34                                       
CONECT    2    1    3    4   35                                       
CONECT    3    2   36   37   38                                       
CONECT    4    2    5    6   39                                       
CONECT    5    4   40                                                 
CONECT    6    4    7    7   31                                       
CONECT    7    6    6    8   17                                       
CONECT    8    7    9   41   42                                       
CONECT    9    8   10   10   16                                       
CONECT   10    9    9   11   12                                       
CONECT   11   10   43   44                                            
CONECT   12   10   13   13                                            
CONECT   13   12   12   14   15                                       
CONECT   14   13   45   46   47                                       
CONECT   15   13   16   16                                            
CONECT   16   15   15    9   48                                       
CONECT   17    7   18   19   19                                       
CONECT   18   17   49   50   51                                       
CONECT   19   17   17   20   31                                       
CONECT   20   19   21   52   53                                       
CONECT   21   20   22   54   55                                       
CONECT   22   21   23                                                 
CONECT   23   22   24   25   25                                       
CONECT   23   26                                                      
CONECT   24   23   56                                                 
CONECT   25   23   23                                                 
CONECT   26   23   27                                                 
CONECT   27   26   28   29   30                                       
CONECT   27   30                                                      
CONECT   28   27   57                                                 
CONECT   29   27   58                                                 
CONECT   30   27   27                                                 
CONECT   31   19    6                                                 
CONECT   32    1                                                      
CONECT   33    1                                                      
CONECT   34    1                                                      
CONECT   35    2                                                      
CONECT   36    3                                                      
CONECT   37    3                                                      
CONECT   38    3                                                      
CONECT   39    4                                                      
CONECT   40    5                                                      
CONECT   41    8                                                      
CONECT   42    8                                                      
CONECT   43   11                                                      
CONECT   44   11                                                      
CONECT   45   14                                                      
CONECT   46   14                                                      
CONECT   47   14                                                      
CONECT   48   16                                                      
CONECT   49   18                                                      
CONECT   50   18                                                      
CONECT   51   18                                                      
CONECT   52   20                                                      
CONECT   53   20                                                      
CONECT   54   21                                                      
CONECT   55   21                                                      
CONECT   56   24                                                      
CONECT   57   28                                                      
CONECT   58   29                                                      
MASTER        0    0    0    0    0    0    0    0   58    0   58    0
END

Download
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
Download
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
Download
View in JSmolView 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
Disposition
Source:
Process
Naturally occurring process:
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP-0.43ALOGPS
logP-6ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)5.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area189.2 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity125.58 m³·mol⁻¹ChemAxon
Polarizability46.15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9813800000-be6335483cae172e16a92017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-7911440000-4b658ddfc94358dd1ffa2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9813800000-be6335483cae172e16a92021-09-05View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-00xs-1368900000-1e4eff19f9ce5ce0973d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-00xs-4419100000-89ecb98fc9c3156fe1c22017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-00di-3941000000-528910db0245fc8319762017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0002-0101900000-a6bad091c8649111d49b2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-00r2-1207900000-4c68794467db876e9d522021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-00di-2933000000-f325b11cce71f2cc69ce2021-09-07View Spectrum
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
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