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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-08-13 17:05:33 UTC

Update Date

2021-09-14 15:45:46 UTC

HMDB ID

HMDB0006865

Secondary Accession Numbers

HMDB0006946
HMDB06865
HMDB06946

Metabolite Identification

Common Name

3-Methyl-1-hydroxybutyl-ThPP

Description

3-Methyl-1-hydroxybutyl-ThPP 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. 3-Methyl-1-hydroxybutyl-ThPP exists in all living organisms, ranging from bacteria to humans. In humans, 3-methyl-1-hydroxybutyl-THPP is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. 3-Methyl-1-hydroxybutyl-ThPP has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-methyl-1-hydroxybutyl-THPP a potential biomarker for the consumption of these foods. 3-Methyl-1-hydroxybutyl-ThPP is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 3-Methyl-1-hydroxybutyl-ThPP.

Structure

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

 
  Mrv0541 02231220542D          
 
 32 33  0  0  0  0            999 V2000
   18.2281  -14.6785    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   18.6068  -13.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8098  -15.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5119  -14.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4192  -14.0795    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.2348  -13.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5432  -14.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7168  -16.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7992  -14.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4156  -13.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6893  -12.5200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2765  -15.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7992  -15.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0763  -14.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9685  -14.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0763  -15.9352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5119  -15.9249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3670  -14.6821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7018  -15.2019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3670  -15.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3938  -14.7543    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.6544  -15.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1271  -15.1330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6451  -15.5805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8192  -14.6854    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.5490  -15.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0705  -15.5116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3938  -13.9293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8192  -13.8604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0438  -12.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2132  -12.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4965  -11.7316    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
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  CHG  1   1   1
M  END

HMDB0006865
     RDKit          3D
3-Methyl-1-hydroxybutyl-ThPP
 61 62  0  0  0  0  0  0  0  0999 V2000
   -3.7181   -5.2320    1.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3454   -3.9866    0.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821   -3.2379    1.2318 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529   -2.1109    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -1.7073   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3517   -0.5140   -1.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1554    0.1849   -0.7321 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3559    1.1095    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6698    1.5468    0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4259    1.6994    2.1822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301    2.8692    0.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1177    3.9459    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8786    4.1589    2.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5850    5.2952    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2188    1.6683    0.5584 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752    0.6788   -0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5602    0.6500   -0.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1944   -0.5434   -0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5708   -0.5352   -0.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198   -1.8613    0.4338 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.5546   -3.1345    0.1565 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4199   -1.6788    2.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8919   -2.0771   -0.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7880   -0.6664    0.1788 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.8606   -0.4547    1.6663 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9509    0.6161   -0.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3459   -0.8127   -0.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885   -0.0496   -1.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4825   -1.0779   -2.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7550   -2.4805   -0.9098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5856   -2.1641   -2.0189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0744   -3.6137   -0.2117 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1223   -5.2821    2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5589   -6.0950    0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8217   -5.2060    1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1097   -1.5150    0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2196    0.1793   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1060   -0.7070   -2.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3965    0.7312    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2899    1.5344    2.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359    3.1449    0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726    2.8368   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1555    3.7292    0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7703    3.9470    2.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6225    5.2404    2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    3.5723    2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072    6.0640    0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6755    5.3526    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    5.2723   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622    0.6831   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0331    1.5571   -0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -1.4643   -0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -0.5470    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0572   -2.3508    2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2474    1.4609   -0.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3539   -0.5959   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4359   -0.7818   -2.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2550   -1.1315   -2.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6547   -2.0192   -1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5412   -1.7613   -1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2434   -2.3327   -2.9797 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
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 16 28  2  0
 28 29  1  0
  5 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 28  7  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 22 54  1  0
 26 55  1  0
 27 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
 31 60  1  0
 31 61  1  0
M  CHG  1   7   1
M  END

 
  Mrv0541 02231220542D          
 
 32 33  0  0  0  0            999 V2000
   18.2281  -14.6785    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   18.6068  -13.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8098  -15.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5119  -14.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4192  -14.0795    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.2348  -13.2085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5432  -14.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7168  -16.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7992  -14.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4156  -13.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6893  -12.5200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2765  -15.2707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7992  -15.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0763  -14.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9685  -14.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0763  -15.9352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5119  -15.9249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3670  -14.6821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7018  -15.2019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3670  -15.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3938  -14.7543    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.6544  -15.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1271  -15.1330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6451  -15.5805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8192  -14.6854    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.5490  -15.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0705  -15.5116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3938  -13.9293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8192  -13.8604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0438  -12.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2132  -12.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4965  -11.7316    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
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  CHG  1   1   1
M  END
> <DATABASE_ID>
HMDB0006865

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC(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/C17H28N4O8P2S/c1-10(2)7-14(22)17-21(9-13-8-19-12(4)20-16(13)18)11(3)15(32-17)5-6-28-31(26,27)29-30(23,24)25/h8,10,14,22H,5-7,9H2,1-4H3,(H4-,18,19,20,23,24,25,26,27)/p+1

> <INCHI_KEY>
OZAWOYZVNPQFFO-UHFFFAOYSA-O

> <FORMULA>
C17H29N4O8P2S

> <MOLECULAR_WEIGHT>
511.447

> <EXACT_MASS>
511.118132638

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
48.363491706368734

> <JCHEM_BIOAVAILABILITY>
0

> <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-3-methylbutyl)-4-methyl-1,3-thiazol-3-ium

> <ALOGPS_LOGP>
-0.29

> <JCHEM_LOGP>
-5.681656853057487

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.197843689193029

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.778305052338096

> <JCHEM_PKA_STRONGEST_BASIC>
5.531117974727769

> <JCHEM_POLAR_SURFACE_AREA>
189.2

> <JCHEM_REFRACTIVITY>
130.2531

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.71e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006865
     RDKit          3D
3-Methyl-1-hydroxybutyl-ThPP
 61 62  0  0  0  0  0  0  0  0999 V2000
   -3.7181   -5.2320    1.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3454   -3.9866    0.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821   -3.2379    1.2318 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529   -2.1109    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -1.7073   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3517   -0.5140   -1.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1554    0.1849   -0.7321 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3559    1.1095    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6698    1.5468    0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4259    1.6994    2.1822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301    2.8692    0.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1177    3.9459    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8786    4.1589    2.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5850    5.2952    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2188    1.6683    0.5584 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752    0.6788   -0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5602    0.6500   -0.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1944   -0.5434   -0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5708   -0.5352   -0.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198   -1.8613    0.4338 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.5546   -3.1345    0.1565 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4199   -1.6788    2.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8919   -2.0771   -0.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7880   -0.6664    0.1788 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.8606   -0.4547    1.6663 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9509    0.6161   -0.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3459   -0.8127   -0.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885   -0.0496   -1.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4825   -1.0779   -2.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7550   -2.4805   -0.9098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5856   -2.1641   -2.0189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0744   -3.6137   -0.2117 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1223   -5.2821    2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5589   -6.0950    0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8217   -5.2060    1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1097   -1.5150    0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2196    0.1793   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1060   -0.7070   -2.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3965    0.7312    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2899    1.5344    2.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359    3.1449    0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726    2.8368   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1555    3.7292    0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7703    3.9470    2.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6225    5.2404    2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    3.5723    2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072    6.0640    0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6755    5.3526    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    5.2723   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622    0.6831   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0331    1.5571   -0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -1.4643   -0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -0.5470    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0572   -2.3508    2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2474    1.4609   -0.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3539   -0.5959   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4359   -0.7818   -2.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2550   -1.1315   -2.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6547   -2.0192   -1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5412   -1.7613   -1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2434   -2.3327   -2.9797 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
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 16 28  2  0
 28 29  1  0
  5 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 28  7  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 22 54  1  0
 26 55  1  0
 27 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
 31 60  1  0
 31 61  1  0
M  CHG  1   7   1
M  END

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      34.026 -27.400   0.000  0.00  0.00           N+1
HETATM    2  C   UNK     0      34.733 -26.031   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      35.112 -28.493   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.689 -26.635   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0      36.249 -26.282   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0      34.038 -24.656   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      36.481 -27.798   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.938 -30.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.359 -27.407   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.509 -24.566   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      34.887 -23.371   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      37.849 -28.505   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.359 -28.955   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.009 -26.642   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      39.141 -27.670   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      30.009 -29.746   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      32.689 -29.726   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      28.685 -27.407   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      40.510 -28.377   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      28.685 -28.955   0.000  0.00  0.00           C+0
HETATM   21  P   UNK     0      41.802 -27.541   0.000  0.00  0.00           P+0
HETATM   22  C   UNK     0      27.355 -29.726   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      43.171 -28.248   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      42.271 -29.084   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0      44.463 -27.413   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0      45.825 -28.113   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      44.932 -28.955   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      41.802 -26.001   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      44.463 -25.873   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      31.815 -23.182   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      30.265 -23.091   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      32.660 -21.899   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                                                       
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   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

COMPND    HMDB0006865
HETATM    1  C1  UNL     1      -3.718  -5.232   1.592  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.345  -3.987   0.846  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.282  -3.238   1.232  1.00  0.00           N  
HETATM    4  C3  UNL     1      -1.953  -2.111   0.549  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.682  -1.707  -0.537  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.352  -0.514  -1.279  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.155   0.185  -0.732  1.00  0.00           N1+
HETATM    8  C6  UNL     1      -1.356   1.109   0.205  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.670   1.547   0.819  1.00  0.00           C  
HETATM   10  O1  UNL     1      -2.426   1.699   2.182  1.00  0.00           O  
HETATM   11  C8  UNL     1      -3.130   2.869   0.276  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.118   3.946   0.585  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.879   4.159   2.046  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.585   5.295   0.024  1.00  0.00           C  
HETATM   15  S1  UNL     1       0.219   1.668   0.558  1.00  0.00           S  
HETATM   16  C12 UNL     1       1.075   0.679  -0.525  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.560   0.650  -0.739  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.194  -0.543  -0.079  1.00  0.00           C  
HETATM   19  O2  UNL     1       4.571  -0.535  -0.297  1.00  0.00           O  
HETATM   20  P1  UNL     1       5.320  -1.861   0.434  1.00  0.00           P  
HETATM   21  O3  UNL     1       4.555  -3.135   0.156  1.00  0.00           O  
HETATM   22  O4  UNL     1       5.420  -1.679   2.112  1.00  0.00           O  
HETATM   23  O5  UNL     1       6.892  -2.077  -0.146  1.00  0.00           O  
HETATM   24  P2  UNL     1       7.788  -0.666   0.179  1.00  0.00           P  
HETATM   25  O6  UNL     1       7.861  -0.455   1.666  1.00  0.00           O  
HETATM   26  O7  UNL     1       6.951   0.616  -0.579  1.00  0.00           O  
HETATM   27  O8  UNL     1       9.346  -0.813  -0.462  1.00  0.00           O  
HETATM   28  C15 UNL     1       0.088  -0.050  -1.119  1.00  0.00           C  
HETATM   29  C16 UNL     1       0.483  -1.078  -2.181  1.00  0.00           C  
HETATM   30  C17 UNL     1      -3.755  -2.480  -0.910  1.00  0.00           C  
HETATM   31  N3  UNL     1      -4.586  -2.164  -2.019  1.00  0.00           N  
HETATM   32  N4  UNL     1      -4.074  -3.614  -0.212  1.00  0.00           N  
HETATM   33  H1  UNL     1      -3.122  -5.282   2.515  1.00  0.00           H  
HETATM   34  H2  UNL     1      -3.559  -6.095   0.932  1.00  0.00           H  
HETATM   35  H3  UNL     1      -4.822  -5.206   1.800  1.00  0.00           H  
HETATM   36  H4  UNL     1      -1.110  -1.515   0.852  1.00  0.00           H  
HETATM   37  H5  UNL     1      -3.220   0.179  -1.311  1.00  0.00           H  
HETATM   38  H6  UNL     1      -2.106  -0.707  -2.343  1.00  0.00           H  
HETATM   39  H7  UNL     1      -3.397   0.731   0.633  1.00  0.00           H  
HETATM   40  H8  UNL     1      -3.290   1.534   2.647  1.00  0.00           H  
HETATM   41  H9  UNL     1      -4.136   3.145   0.641  1.00  0.00           H  
HETATM   42  H10 UNL     1      -3.173   2.837  -0.854  1.00  0.00           H  
HETATM   43  H11 UNL     1      -1.156   3.729   0.069  1.00  0.00           H  
HETATM   44  H12 UNL     1      -2.770   3.947   2.682  1.00  0.00           H  
HETATM   45  H13 UNL     1      -1.623   5.240   2.249  1.00  0.00           H  
HETATM   46  H14 UNL     1      -1.052   3.572   2.429  1.00  0.00           H  
HETATM   47  H15 UNL     1      -2.007   6.064   0.551  1.00  0.00           H  
HETATM   48  H16 UNL     1      -3.675   5.353   0.210  1.00  0.00           H  
HETATM   49  H17 UNL     1      -2.357   5.272  -1.056  1.00  0.00           H  
HETATM   50  H18 UNL     1       2.762   0.683  -1.830  1.00  0.00           H  
HETATM   51  H19 UNL     1       3.033   1.557  -0.312  1.00  0.00           H  
HETATM   52  H20 UNL     1       2.814  -1.464  -0.584  1.00  0.00           H  
HETATM   53  H21 UNL     1       2.998  -0.547   0.991  1.00  0.00           H  
HETATM   54  H22 UNL     1       6.057  -2.351   2.437  1.00  0.00           H  
HETATM   55  H23 UNL     1       7.247   1.461  -0.180  1.00  0.00           H  
HETATM   56  H24 UNL     1       9.354  -0.596  -1.445  1.00  0.00           H  
HETATM   57  H25 UNL     1       1.436  -0.782  -2.658  1.00  0.00           H  
HETATM   58  H26 UNL     1      -0.255  -1.131  -2.981  1.00  0.00           H  
HETATM   59  H27 UNL     1       0.655  -2.019  -1.647  1.00  0.00           H  
HETATM   60  H28 UNL     1      -5.541  -1.761  -1.860  1.00  0.00           H  
HETATM   61  H29 UNL     1      -4.243  -2.333  -2.980  1.00  0.00           H  
CONECT    1    2   33   34   35
CONECT    2    3    3   32
CONECT    3    4
CONECT    4    5    5   36
CONECT    5    6   30
CONECT    6    7   37   38
CONECT    7    8    8   28
CONECT    8    9   15
CONECT    9   10   11   39
CONECT   10   40
CONECT   11   12   41   42
CONECT   12   13   14   43
CONECT   13   44   45   46
CONECT   14   47   48   49
CONECT   15   16
CONECT   16   17   28   28
CONECT   17   18   50   51
CONECT   18   19   52   53
CONECT   19   20
CONECT   20   21   21   22   23
CONECT   22   54
CONECT   23   24
CONECT   24   25   25   26   27
CONECT   26   55
CONECT   27   56
CONECT   28   29
CONECT   29   57   58   59
CONECT   30   31   32   32
CONECT   31   60   61
END

HMDB0006865
     RDKit          3D
3-Methyl-1-hydroxybutyl-ThPP
 61 62  0  0  0  0  0  0  0  0999 V2000
   -3.7181   -5.2320    1.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3454   -3.9866    0.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821   -3.2379    1.2318 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529   -2.1109    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6817   -1.7073   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3517   -0.5140   -1.2794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1554    0.1849   -0.7321 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.3559    1.1095    0.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6698    1.5468    0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4259    1.6994    2.1822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1301    2.8692    0.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1177    3.9459    0.5854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8786    4.1589    2.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5850    5.2952    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2188    1.6683    0.5584 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752    0.6788   -0.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5602    0.6500   -0.7388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1944   -0.5434   -0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4199   -1.6788    2.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8919   -2.0771   -0.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7880   -0.6664    0.1788 P   0  0  0  0  0  5  0  0  0  0  0  0
    7.8606   -0.4547    1.6663 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9509    0.6161   -0.5786 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3459   -0.8127   -0.4621 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885   -0.0496   -1.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4825   -1.0779   -2.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7550   -2.4805   -0.9098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5856   -2.1641   -2.0189 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0744   -3.6137   -0.2117 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1223   -5.2821    2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5589   -6.0950    0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8217   -5.2060    1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1097   -1.5150    0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2196    0.1793   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1060   -0.7070   -2.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3965    0.7312    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2899    1.5344    2.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359    3.1449    0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726    2.8368   -0.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1555    3.7292    0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7703    3.9470    2.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6225    5.2404    2.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    3.5723    2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0072    6.0640    0.5509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6755    5.3526    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    5.2723   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622    0.6831   -1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0331    1.5571   -0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8136   -1.4643   -0.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979   -0.5470    0.9906 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0572   -2.3508    2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2474    1.4609   -0.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3539   -0.5959   -1.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4359   -0.7818   -2.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2550   -1.1315   -2.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6547   -2.0192   -1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5412   -1.7613   -1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2434   -2.3327   -2.9797 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
 12 13  1  0
 12 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 16 28  2  0
 28 29  1  0
  5 30  1  0
 30 31  1  0
 30 32  2  0
 32  2  1  0
 28  7  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 22 54  1  0
 26 55  1  0
 27 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
 31 60  1  0
 31 61  1  0
M  CHG  1   7   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Methyl-1-hydroxybutyl-TPP	Kegg

Chemical Formula

C₁₇H₂₉N₄O₈P₂S

Average Molecular Weight

511.447

Monoisotopic Molecular Weight

511.118132638

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)CC(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/C17H28N4O8P2S/c1-10(2)7-14(22)17-21(9-13-8-19-12(4)20-16(13)18)11(3)15(32-17)5-6-28-31(26,27)29-30(23,24)25/h8,10,14,22H,5-7,9H2,1-4H3,(H4-,18,19,20,23,24,25,26,27)/p+1

InChI Key

OZAWOYZVNPQFFO-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiamine 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

thiamine phosphate (CHEBI:80220 )

Ontology

Physiological effect

Adverse health effect

Genetic disorder

Inborn errors of metabolism

Ingestion

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Spectral Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.077 g/L	ALOGPS
logP	10^(-0.29) g/L	ALOGPS
logP	10^(-5.7) g/L	ChemAxon
logS	10^(-3.8) g/L	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	5.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.2 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	130.25 m³·mol⁻¹	ChemAxon
Polarizability	48.36 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	215.918	31661259
DarkChem	[M-H]-	209.899	31661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-1-hydroxybutyl-ThPP,1TMS,#1	CC1=NC=C(C[N+]2=C(C(CC(C)C)O[Si](C)(C)C)SC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N)=N1	3944.4	Semi standard non polar	https://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TMS,#2	CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N)=N1	3974.7	Semi standard non polar	https://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TMS,#3	CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N1	3959.6	Semi standard non polar	https://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TMS,#4	CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N1	3976.8	Semi standard non polar	https://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TBDMS,#1	CC1=NC=C(C[N+]2=C(C(CC(C)C)O[Si](C)(C)C(C)(C)C)SC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N)=N1	4167.3	Semi standard non polar	https://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TBDMS,#2	CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N)=N1	4172.5	Semi standard non polar	https://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TBDMS,#3	CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	4160.0	Semi standard non polar	https://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TBDMS,#4	CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	4178.8	Semi standard non polar	https://arxiv.org/abs/1905.12712

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-8712900000-44639cddf5ac88be9b05	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP GC-MS (1 TMS) - 70eV, Positive	splash10-014j-6262390000-db7a22cbb385f200f0fd	2017-10-06	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 - 3-Methyl-1-hydroxybutyl-ThPP 10V, Positive-QTOF	splash10-01qi-1378940000-15be0e4fc27c59d8eb15	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP 20V, Positive-QTOF	splash10-0541-4309200000-c17630fd91cf03a198a9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP 40V, Positive-QTOF	splash10-00dj-3952000000-1c97b66ad8638eecd445	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP 10V, Positive-QTOF	splash10-03di-0200790000-01564e480d3ab339187c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP 20V, Positive-QTOF	splash10-007k-1409710000-76598bfc6e49c4250a33	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP 40V, Positive-QTOF	splash10-00di-3932000000-aa3b8e91eab38ba117e9	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Valine, leucine and isoleucine degradation	Not Available
Beta-Ketothiolase Deficiency		Not Available
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency		Not Available
Propionic Acidemia		Not Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024121

KNApSAcK ID

Not Available

Chemspider ID

22378483

KEGG Compound ID

C15974

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724625

PDB ID

Not Available

ChEBI ID

80220

Food Biomarker Ontology

Not Available

VMH ID

3M1HBTPP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not 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

Ketoleucine + Thiamine pyrophosphate → 3-Methyl-1-hydroxybutyl-ThPP + Carbon dioxide	details
3-Methyl-1-hydroxybutyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(3-methylbutanoyl)dihydrolipoyllysine + Thiamine pyrophosphate	details

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

Ketoleucine + Thiamine pyrophosphate → 3-Methyl-1-hydroxybutyl-ThPP + Carbon dioxide	details
3-Methyl-1-hydroxybutyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(3-methylbutanoyl)dihydrolipoyllysine + Thiamine pyrophosphate	details

Showing metabocard for 3-Methyl-1-hydroxybutyl-ThPP (HMDB0006865)

MOL for HMDB0006865 (3-Methyl-1-hydroxybutyl-ThPP)

3D MOL for HMDB0006865 (3-Methyl-1-hydroxybutyl-ThPP)

3D SDF for HMDB0006865 (3-Methyl-1-hydroxybutyl-ThPP)

3D-SDF for HMDB0006865 (3-Methyl-1-hydroxybutyl-ThPP)

PDB for HMDB0006865 (3-Methyl-1-hydroxybutyl-ThPP)

3D PDB for HMDB0006865 (3-Methyl-1-hydroxybutyl-ThPP)

SMILES for HMDB0006865 (3-Methyl-1-hydroxybutyl-ThPP)

INCHI for HMDB0006865 (3-Methyl-1-hydroxybutyl-ThPP)

Structure for HMDB0006865 (3-Methyl-1-hydroxybutyl-ThPP)

3D Structure for HMDB0006865 (3-Methyl-1-hydroxybutyl-ThPP)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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Reactions