MiMeDB: Showing metabocard for Thiamine pyrophosphate (MMDBc0029635)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:35:31 UTC

Update Date

2024-10-13 06:32:47 UTC

Metabolite ID

MMDBc0029635

Metabolite Identification

Common Name

Thiamine pyrophosphate

Description

Thiamine pyrophosphate (TPP) is the active form of thiamine, and it serves as a cofactor for several enzymes involved primarily in carbohydrate catabolism. The enzymes are important in the biosynthesis of a number of cell constituents and for the production of reducing equivalents used in oxidant stress defenses and in biosyntheses and for synthesis of pentoses used as nucleic acid precursors. The chemical structure of TPP is that of an aromatic methylaminopyrimidine ring, linked via a methylene bridge to a methylthiazolium ring with a pyrophosphate group attached to a hydroxyethyl side chain. In non-enzymatic model studies it has been demonstrated that the thiazolium ring can catalyse reactions which are similar to those of TPP-dependent enzymes but several orders of magnitude slower. Using infrared and NMR spectrophotometry it has been shown that the dissociation of the proton from C2 of the thiazolium ring is necessary for catalysis; the abstraction of the proton leads to the formation of a carbanion (ylid) with the potential for a nucleophilic attack on the carbonyl group of the substrate. In all TPP-dependent enzymes the abstraction of the proton from the C2 atom is the first step in catalysis, which is followed by a nucleophilic attack of this carbanion on the substrate. Subsequent cleavage of a C-C bond releases the first product with formation of a second carbanion (2-greek small letter alpha-carbanion or enamine). The formation of this 2-greek small letter alpha-carbanion is the second feature of TPP catalysis common to all TPP-dependent enzymes. Depending on the enzyme and the substrate(s), the reaction intermediates and products differ. Methyl-branched fatty acids, as phytanic acid, undergo peroxisomal beta-oxidation in which they are shortened by 1 carbon atom. This process includes four steps: activation, 2-hydroxylation, thiamine pyrophosphate dependent cleavage and aldehyde dehydrogenation. In the third step, 2-hydroxy-3-methylacyl-CoA is cleaved in the peroxisomal matrix by 2-hydroxyphytanoyl-CoA lyase (2-HPCL), which uses thiamine pyrophosphate (TPP) as cofactor. (PMID: 12694175 , 11899071 , 9924800 )

Structure

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


  Mrv1652309042000222D          

 26 27  0  0  0  0            999 V2000
10003.235710001.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.522010001.0910    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10003.949210001.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.870310001.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.255910000.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.949210000.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.667010001.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.870310002.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.185510001.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.424810000.3196    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10003.2357 9999.8552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.6670 9999.8552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.378610001.0910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.472010001.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.378610000.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.758110001.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.0922 9999.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.044010001.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.330010001.0910    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9997.615910001.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.743310000.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.919010000.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.902110001.0910    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9997.313210000.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.184010001.5073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.488810000.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  4  8  1  0  0  0  0
  6 11  1  0  0  0  0
  9 14  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
  9  4  2  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  5  2  2  0  0  0  0
  2  4  1  0  0  0  0
  3  7  2  0  0  0  0
  7 13  1  0  0  0  0
 13 15  2  0  0  0  0
 15 12  1  0  0  0  0
 12  6  2  0  0  0  0
  3  6  1  0  0  0  0
M  CHG  1   2   1
M  END

HMDB0001372
     RDKit          3D
Thiamine pyrophosphate
 45 46  0  0  0  0  0  0  0  0999 V2000
   -5.8388    2.6750    1.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    1.6885    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6652    1.8898    0.7954 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9166    1.0121    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4545   -0.1114   -0.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7630   -1.1185   -1.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -1.0313   -1.2319 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.6014   -0.4642   -2.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0219   -0.7202   -1.8179 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7828   -1.5526   -0.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -2.0291    0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6912   -0.8148    0.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2726   -0.5627   -0.2918 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249    0.6127   -0.3348 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.6560    0.9776   -1.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932    1.9562    0.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9532    0.0233    0.1885 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0880    1.2137   -0.2018 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.9937    1.4308   -1.7034 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7103    2.7068    0.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6515    0.6971    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -1.5918   -0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2355   -2.3172    0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8265   -0.2975   -0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5412   -1.3919   -0.8546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5361    0.6160    0.3909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7895    2.1630    1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3626    3.0017    2.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1077    3.5233    1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522    1.2203    0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0559   -0.9921   -2.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -2.1361   -0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488    0.0479   -3.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3973   -2.8467    0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1981   -2.2384    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -1.1362    1.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1207    0.0459    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218    2.0673    0.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8885    3.4288   -0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1005    1.5087    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2161   -2.7392    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -3.1958    1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4106   -1.6305    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9195   -2.1269   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6876   -1.4612   -1.8704 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 10 22  2  0
 22 23  1  0
  5 24  1  0
 24 25  1  0
 24 26  2  0
 26  2  1  0
 22  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 16 38  1  0
 20 39  1  0
 21 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
 25 44  1  0
 25 45  1  0
M  CHG  1   7   1
M  END


  Mrv1652309042000222D          

 26 27  0  0  0  0            999 V2000
10003.235710001.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.522010001.0910    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10003.949210001.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.870310001.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.255910000.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.949210000.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.667010001.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.870310002.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.185510001.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.424810000.3196    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
10003.2357 9999.8552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10004.6670 9999.8552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10005.378610001.0910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10000.472010001.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.378610000.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.758110001.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.0922 9999.8552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.044010001.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.330010001.0910    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9997.615910001.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.743310000.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.919010000.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.902110001.0910    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9997.313210000.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.184010001.5073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.488810000.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  4  8  1  0  0  0  0
  6 11  1  0  0  0  0
  9 14  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
  9  4  2  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  5  2  2  0  0  0  0
  2  4  1  0  0  0  0
  3  7  2  0  0  0  0
  7 13  1  0  0  0  0
 13 15  2  0  0  0  0
 15 12  1  0  0  0  0
 12  6  2  0  0  0  0
  3  6  1  0  0  0  0
M  CHG  1   2   1
M  END
> <DATABASE_ID>
MMDBc0029635

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1

> <INCHI_KEY>
AYEKOFBPNLCAJY-UHFFFAOYSA-O

> <FORMULA>
C12H19N4O7P2S

> <MOLECULAR_WEIGHT>
425.314

> <EXACT_MASS>
425.044967696

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
36.9637991067903

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

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

> <ALOGPS_LOGP>
-1.21

> <JCHEM_LOGP>
-5.79955409211528

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.2177664195972664

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7783059358514746

> <JCHEM_PKA_STRONGEST_BASIC>
5.534004899065866

> <JCHEM_POLAR_SURFACE_AREA>
168.97

> <JCHEM_REFRACTIVITY>
95.1455

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiamin pyrophosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001372
     RDKit          3D
Thiamine pyrophosphate
 45 46  0  0  0  0  0  0  0  0999 V2000
   -5.8388    2.6750    1.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    1.6885    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6652    1.8898    0.7954 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9166    1.0121    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4545   -0.1114   -0.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7630   -1.1185   -1.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -1.0313   -1.2319 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.6014   -0.4642   -2.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0219   -0.7202   -1.8179 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7828   -1.5526   -0.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -2.0291    0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6912   -0.8148    0.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2726   -0.5627   -0.2918 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249    0.6127   -0.3348 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.6560    0.9776   -1.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932    1.9562    0.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9532    0.0233    0.1885 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0880    1.2137   -0.2018 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.9937    1.4308   -1.7034 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7103    2.7068    0.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6515    0.6971    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -1.5918   -0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2355   -2.3172    0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8265   -0.2975   -0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5412   -1.3919   -0.8546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5361    0.6160    0.3909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7895    2.1630    1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3626    3.0017    2.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1077    3.5233    1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522    1.2203    0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0559   -0.9921   -2.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -2.1361   -0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488    0.0479   -3.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3973   -2.8467    0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1981   -2.2384    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -1.1362    1.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1207    0.0459    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218    2.0673    0.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8885    3.4288   -0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1005    1.5087    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2161   -2.7392    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -3.1958    1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4106   -1.6305    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9195   -2.1269   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6876   -1.4612   -1.8704 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 10 22  2  0
 22 23  1  0
  5 24  1  0
 24 25  1  0
 24 26  2  0
 26  2  1  0
 22  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 16 38  1  0
 20 39  1  0
 21 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
 25 44  1  0
 25 45  1  0
M  CHG  1   7   1
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8672.7078669.476   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8671.3748668.703   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0    8674.0398668.703   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8670.1588669.646   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8670.8788667.263   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8674.0398667.164   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8675.3788669.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.1588671.186   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.8808668.703   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0    8669.3268667.263   0.000  0.00  0.00           S+0
HETATM   11  N   UNK     0    8672.7078666.396   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0    8675.3788666.396   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0    8676.7078668.703   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0    8667.5488669.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8676.7078667.164   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.2158668.703   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8678.0398666.396   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8664.8828669.476   0.000  0.00  0.00           O+0
HETATM   19  P   UNK     0    8663.5498668.703   0.000  0.00  0.00           P+0
HETATM   20  O   UNK     0    8662.2168669.476   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0    8664.3218667.370   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8662.7828667.370   0.000  0.00  0.00           O+0
HETATM   23  P   UNK     0    8660.8848668.703   0.000  0.00  0.00           P+0
HETATM   24  O   UNK     0    8661.6518667.370   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0    8659.5438669.480   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0    8660.1128667.370   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5    4                                                  
CONECT    3    1    7    6                                                  
CONECT    4    8    9    2                                                  
CONECT    5   10    2                                                       
CONECT    6   11   12    3                                                  
CONECT    7    3   13                                                       
CONECT    8    4                                                            
CONECT    9   14    4   10                                                  
CONECT   10    9    5                                                       
CONECT   11    6                                                            
CONECT   12   15    6                                                       
CONECT   13    7   15                                                       
CONECT   14    9   16                                                       
CONECT   15   17   13   12                                                  
CONECT   16   14   18                                                       
CONECT   17   15                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19   23                                                       
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   20   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0001372
HETATM    1  C1  UNL     1      -5.839   2.675   1.710  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.988   1.688   0.940  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.665   1.890   0.795  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.917   1.012   0.103  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.455  -0.111  -0.479  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.763  -1.118  -1.240  1.00  0.00           C  
HETATM    7  N2  UNL     1      -1.288  -1.031  -1.232  1.00  0.00           N1+
HETATM    8  C6  UNL     1      -0.601  -0.464  -2.234  1.00  0.00           C  
HETATM    9  S1  UNL     1       1.022  -0.720  -1.818  1.00  0.00           S  
HETATM   10  C7  UNL     1       0.783  -1.553  -0.354  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.783  -2.029   0.662  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.691  -0.815   0.958  1.00  0.00           C  
HETATM   13  O1  UNL     1       3.273  -0.563  -0.292  1.00  0.00           O  
HETATM   14  P1  UNL     1       4.425   0.613  -0.335  1.00  0.00           P  
HETATM   15  O2  UNL     1       4.656   0.978  -1.810  1.00  0.00           O  
HETATM   16  O3  UNL     1       4.093   1.956   0.585  1.00  0.00           O  
HETATM   17  O4  UNL     1       5.953   0.023   0.189  1.00  0.00           O  
HETATM   18  P2  UNL     1       7.088   1.214  -0.202  1.00  0.00           P  
HETATM   19  O5  UNL     1       6.994   1.431  -1.703  1.00  0.00           O  
HETATM   20  O6  UNL     1       6.710   2.707   0.537  1.00  0.00           O  
HETATM   21  O7  UNL     1       8.652   0.697   0.204  1.00  0.00           O  
HETATM   22  C10 UNL     1      -0.593  -1.592  -0.261  1.00  0.00           C  
HETATM   23  C11 UNL     1      -1.236  -2.317   0.930  1.00  0.00           C  
HETATM   24  C12 UNL     1      -4.826  -0.298  -0.317  1.00  0.00           C  
HETATM   25  N3  UNL     1      -5.541  -1.392  -0.855  1.00  0.00           N  
HETATM   26  N4  UNL     1      -5.536   0.616   0.391  1.00  0.00           N  
HETATM   27  H1  UNL     1      -6.789   2.163   1.952  1.00  0.00           H  
HETATM   28  H2  UNL     1      -5.363   3.002   2.632  1.00  0.00           H  
HETATM   29  H3  UNL     1      -6.108   3.523   1.031  1.00  0.00           H  
HETATM   30  H4  UNL     1      -1.852   1.220   0.003  1.00  0.00           H  
HETATM   31  H5  UNL     1      -3.056  -0.992  -2.330  1.00  0.00           H  
HETATM   32  H6  UNL     1      -3.104  -2.136  -0.993  1.00  0.00           H  
HETATM   33  H7  UNL     1      -1.049   0.048  -3.119  1.00  0.00           H  
HETATM   34  H8  UNL     1       2.397  -2.847   0.359  1.00  0.00           H  
HETATM   35  H9  UNL     1       1.198  -2.238   1.602  1.00  0.00           H  
HETATM   36  H10 UNL     1       3.462  -1.136   1.687  1.00  0.00           H  
HETATM   37  H11 UNL     1       2.121   0.046   1.331  1.00  0.00           H  
HETATM   38  H12 UNL     1       3.122   2.067   0.770  1.00  0.00           H  
HETATM   39  H13 UNL     1       6.889   3.429  -0.091  1.00  0.00           H  
HETATM   40  H14 UNL     1       9.100   1.509   0.608  1.00  0.00           H  
HETATM   41  H15 UNL     1      -2.216  -2.739   0.646  1.00  0.00           H  
HETATM   42  H16 UNL     1      -0.610  -3.196   1.199  1.00  0.00           H  
HETATM   43  H17 UNL     1      -1.411  -1.630   1.764  1.00  0.00           H  
HETATM   44  H18 UNL     1      -5.919  -2.127  -0.248  1.00  0.00           H  
HETATM   45  H19 UNL     1      -5.688  -1.461  -1.870  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3    3   26
CONECT    3    4
CONECT    4    5    5   30
CONECT    5    6   24
CONECT    6    7   31   32
CONECT    7    8    8   22
CONECT    8    9   33
CONECT    9   10
CONECT   10   11   22   22
CONECT   11   12   34   35
CONECT   12   13   36   37
CONECT   13   14
CONECT   14   15   15   16   17
CONECT   16   38
CONECT   17   18
CONECT   18   19   19   20   21
CONECT   20   39
CONECT   21   40
CONECT   22   23
CONECT   23   41   42   43
CONECT   24   25   26   26
CONECT   25   44   45
END

HMDB0001372
     RDKit          3D
Thiamine pyrophosphate
 45 46  0  0  0  0  0  0  0  0999 V2000
   -5.8388    2.6750    1.7095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9876    1.6885    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6652    1.8898    0.7954 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9166    1.0121    0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4545   -0.1114   -0.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7630   -1.1185   -1.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -1.0313   -1.2319 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.6014   -0.4642   -2.2339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0219   -0.7202   -1.8179 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7828   -1.5526   -0.3542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -2.0291    0.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6912   -0.8148    0.9585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2726   -0.5627   -0.2918 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4249    0.6127   -0.3348 P   0  0  0  0  0  5  0  0  0  0  0  0
    4.6560    0.9776   -1.8102 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932    1.9562    0.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9532    0.0233    0.1885 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0880    1.2137   -0.2018 P   0  0  0  0  0  5  0  0  0  0  0  0
    6.9937    1.4308   -1.7034 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7103    2.7068    0.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6515    0.6971    0.2036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927   -1.5918   -0.2606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2355   -2.3172    0.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8265   -0.2975   -0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5412   -1.3919   -0.8546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5361    0.6160    0.3909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7895    2.1630    1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3626    3.0017    2.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1077    3.5233    1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8522    1.2203    0.0032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0559   -0.9921   -2.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -2.1361   -0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488    0.0479   -3.1187 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3973   -2.8467    0.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1981   -2.2384    1.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618   -1.1362    1.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1207    0.0459    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218    2.0673    0.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8885    3.4288   -0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1005    1.5087    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2161   -2.7392    0.6464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6096   -3.1958    1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4106   -1.6305    1.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9195   -2.1269   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6876   -1.4612   -1.8704 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
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 18 21  1  0
 10 22  2  0
 22 23  1  0
  5 24  1  0
 24 25  1  0
 24 26  2  0
 26  2  1  0
 22  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  8 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 16 38  1  0
 20 39  1  0
 21 40  1  0
 23 41  1  0
 23 42  1  0
 23 43  1  0
 25 44  1  0
 25 45  1  0
M  CHG  1   7   1
M  END

Synonyms

Value	Source
Thiamin diphosphate	ChEBI
Thiamin pyrophosphate	ChEBI
Thiamine diphosphate	ChEBI
THPP	ChEBI
TPP	ChEBI
Thiamin diphosphoric acid	Generator
Thiamin pyrophosphoric acid	Generator
Thiamine diphosphoric acid	Generator
Thiamine pyrophosphoric acid	Generator
Thaimine pyrophosphate	HMDB
Thiamin-ppi	HMDB
Thiamine-ppi	HMDB
Thiamine-pyrophosphate	HMDB
Cocarboxylase	HMDB
Berolase	HMDB
Pyrophosphate, thiamine	HMDB

Molecular Formula

C₁₂H₁₉N₄O₇P₂S

Average Mass

425.314

Monoisotopic Mass

425.044967696

IUPAC Name

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

Traditional Name

thiamin pyrophosphate

CAS Registry Number

154-87-0

SMILES

CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N

InChI Identifier

InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1

InChI Key

AYEKOFBPNLCAJY-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
4,5-disubstituted 1,3-thiazole
Monoalkyl phosphate
Hydropyrimidine
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Imidolactam
Thiazole
Azole
Heteroaromatic compound
Azacycle
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic cation
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1,3-thiazolium cation (CHEBI:9532 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-5.8	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	5.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	168.97 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	95.15 m³·mol⁻¹	ChemAxon
Polarizability	36.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-9734000000-83738512818790cf1cc5	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0201900000-9ca110d3800e4ebfad43	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-0900000000-dad8835a4b26b1df86c4	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-2900000000-83b0eb52fe05e7097aff	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-0000900000-538ee08c2fc9a905eaad	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0309000000-b196fd5684e86907d04e	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0udi-0409000000-088cf88d5056ce245770	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9822000000-011b97ebb9fdcebffc93	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9200000000-2ecd5ee7eb283c5cd990	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-004i-0001900000-59ea8d394aed62700202	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00b9-0614900000-08f09a377f03019f4457	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00di-0911000000-de2b56b98b01c6409b09	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00di-0900000000-7d75ca5105912446e47b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00di-2900000000-d632b8688f17a7a01de0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-0000900000-538ee08c2fc9a905eaad	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0309000000-b196fd5684e86907d04e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0409000000-088cf88d5056ce245770	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9822000000-670f784e69ef56047333	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9200000000-2ecd5ee7eb283c5cd990	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-0001900000-59ea8d394aed62700202	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0100900000-2d5d6c77c0c7e2d2d28a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aba-8146900000-e4efbc495cf0eb380395	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-4911100000-7e4a6eda3f297e8051b7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000900000-08198f6dfeaa404b8b0f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9100200000-2d9e7e5d87267ce83dcc	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004j-9200000000-a470e5de9f124c159e0e	2016-09-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Brain
Cerebrospinal Fluid (CSF)
Erythrocyte
Feces
Fibroblasts

Tissue Locations

Brain
Erythrocyte
Fibroblasts

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191688	Pyruvate dehydrogenase E1 component subunit beta, mitochondrial	Enzyme	P11177	Homo sapiens
MMDBp0191720	Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial	Enzyme	P08559	Homo sapiens
MMDBp0191724	Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial	Enzyme	P29803	Homo sapiens
MMDBp0191969	2-oxoisovalerate dehydrogenase subunit beta, mitochondrial	Enzyme	P21953	Homo sapiens
MMDBp0191970	2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial	Unknown	P12694	Homo sapiens
MMDBp0192105	2-oxoglutarate dehydrogenase, mitochondrial	Enzyme	Q02218	Homo sapiens
MMDBp0192275	Thiamin pyrophosphokinase 1	Enzyme	Q9H3S4	Homo sapiens
MMDBp0192420	Transketolase-like protein 1	Unknown	P51854	Homo sapiens
MMDBp0192425	Transketolase	Unknown	P29401	Homo sapiens
MMDBp0192497	Ectonucleoside triphosphate diphosphohydrolase 5	Unknown	O75356	Homo sapiens
MMDBp0193129	Thiamine-triphosphatase	Enzyme	Q9BU02	Homo sapiens
MMDBp0194056	Transketolase-like protein 2	Unknown	Q9H0I9	Homo sapiens
MMDBp0194154	Acetolactate synthase-like protein	Unknown	A1L0T0	Homo sapiens
MMDBp0195496	2-hydroxyacyl-CoA lyase 1	Unknown	Q9UJ83	Homo sapiens
MMDBp0195851	Probable 2-oxoglutarate dehydrogenase E1 component DHKTD1, mitochondrial	Enzyme	Q96HY7	Homo sapiens
MMDBp0195852	2-oxoglutarate dehydrogenase-like, mitochondrial	Enzyme	Q9ULD0	Homo sapiens
MMDBp0196230	Cancer-related nucleoside-triphosphatase	Enzyme	Q9BSD7	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank
2-Amino-3-Carboxymuconate Semialdehyde Degradation

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0002205	Thiamine pyrophosphate	Thiamine monophosphate	Not Available	VMH; KEGG	30371894
MMDBr0002207	Thiamine pyrophosphate	Thiamine monophosphate	Not Available	VMH; KEGG	30371894
MMDBr0002237	Thiamine triphosphate	Thiamine pyrophosphate	thiamine triphosphatase	VMH; KEGG	30371894
MMDBr0002258	Thiamine pyrophosphate	Thiamine triphosphate	Not Available	VMH; KEGG	30371894
MMDBr0002472	Oxoglutaric acid	3-Carboxy-1-hydroxypropylthiamine diphosphate	oxoglutarate (alpha-ketoglutarate) dehydrogenase (lipoamide)	VMH	10676873 3207422
MMDBr0002627	3-Carboxy-1-hydroxypropylthiamine diphosphate	(S)-Succinyldihydrolipoamide	oxoglutarate (alpha-ketoglutarate) dehydrogenase (lipoamide)	VMH	10676873
MMDBr0007581	Thiamine	Thiamine pyrophosphate	Not Available	VMH; KEGG	30371894
MMDBr0007677	3-Carboxy-1-hydroxypropylthiamine diphosphate	(S)-Succinyldihydrolipoamide	Not Available	VMH	30371894
MMDBr0008013	Oxoglutaric acid	3-Carboxy-1-hydroxypropylthiamine diphosphate	Not Available	VMH	30371894
MMDBr0008351	alpha-Ketoisovaleric acid	2-Methyl-1-hydroxypropyl-TPP	Not Available	VMH	30371894
MMDBr0008352	3-Methyl-2-oxovaleric acid	2-Methyl-1-hydroxybutyl-ThPP	Not Available	VMH	30371894
MMDBr0008353	Ketoleucine	3-Methyl-1-hydroxybutyl-TPP	Not Available	VMH	30371894
MMDBr0008358	3-Methyl-1-hydroxybutyl-TPP	S-(3-Methylbutanoyl)-dihydrolipoamide-E	Not Available	VMH	30371894
MMDBr0008359	2-Methyl-1-hydroxybutyl-ThPP	S-(2-Methylbutanoyl)-dihydrolipoamide	Not Available	VMH	30371894
MMDBr0008360	2-Methyl-1-hydroxypropyl-TPP	S-(2-Methylpropionyl)-dihydrolipoamide-E	Not Available	VMH	30371894
MMDBr0010650	Thiamine pyrophosphate	2-(a-Hydroxyethyl)thiamine diphosphate	pyruvate dehydrogenase (lipoamide) alpha 1	VMH; KEGG	30371894
MMDBr0010976	Thiamine pyrophosphate	Thiamine	Not Available	VMH	30371894
MMDBr0012620	Thiamine monophosphate	Thiamine pyrophosphate	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Alzheimer's disease	Slight Decrease	Association	Human Cerebrospinal Fluid (CSF)	HMDB	12111441
Cerebrocortical degeneration		Association	Human Blood	HMDB	17642321

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	188	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	390	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	128	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human saliva; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human subgingival plaque; Human supragingival plaque; Human urine	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	2	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	4	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown
Bacteria	Aquificae	1
Archaea/Archaea	Euryarchaeota	8		Metabolic reconstruction
Archaea/Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Cyanobacteria	2
Archaea/Archaea	Crenarchaeota	1		Metabolic reconstruction

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0025	0.0017			uM	Adult (>18 years old)	Both	Alzheimer's disease	HMDB	12111441
Human Blood	Detected and Quantified	0.034		0	0.066	uM	Adult (>18 years old)	Not Specified	Cerebrocortical Degeneration	HMDB	17642321
Human Cerebrospinal fluid (csf)	Detected and Quantified	0.0032	0.0022			uM	Adult (>18 years old)	Both	Normal	HMDB	12111441
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Erythrocyte	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0001372

DrugBank ID

DB01987

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

THIAMINE-PYROPHOSPHATE

BiGG ID

33732

Wikipedia Link

Thiamine pyrophosphate

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Kjosen B, Seim SH: The transketolase assay of thiamine in some diseases. Am J Clin Nutr. 1977 Oct;30(10):1591-6. doi: 10.1093/ajcn/30.10.1591. [PubMed:910736 ]
Fidanza F, Simonetti MS, Floridi A, Codini M, Fidanza R: Comparison of methods for thiamin and riboflavin nutriture in man. Int J Vitam Nutr Res. 1989;59(1):40-7. [PubMed:2722424 ]
Tate JR, Nixon PF: Measurement of Michaelis constant for human erythrocyte transketolase and thiamin diphosphate. Anal Biochem. 1987 Jan;160(1):78-87. doi: 10.1016/0003-2697(87)90616-6. [PubMed:3565758 ]
Baines M: Improved high performance liquid chromatographic determination of thiamin diphosphate in erythrocytes. Clin Chim Acta. 1985 Nov 29;153(1):43-8. doi: 10.1016/0009-8981(85)90137-8. [PubMed:4075519 ]
Floridi A, Pupita M, Palmerini CA, Fini C, Alberti Fidanza A: Thiamine pyrophosphate determination in whole blood and erythrocytes by high performance liquid chromatography. Int J Vitam Nutr Res. 1984;54(2-3):165-71. [PubMed:6500839 ]
Warnock LG: The measurement of erythrocyte thiamin pyrophosphate by high-performance liquid chromatography. Anal Biochem. 1982 Nov 1;126(2):394-7. doi: 10.1016/0003-2697(82)90533-4. [PubMed:7158773 ]
Duffy P, Morris H, Neilson G: Thiamin status of a Melanesian population. Am J Clin Nutr. 1981 Aug;34(8):1584-92. doi: 10.1093/ajcn/34.8.1584. [PubMed:7270482 ]
Lavoie J, Butterworth RF: Reduced activities of thiamine-dependent enzymes in brains of alcoholics in the absence of Wernicke's encephalopathy. Alcohol Clin Exp Res. 1995 Aug;19(4):1073-7. doi: 10.1111/j.1530-0277.1995.tb00991.x. [PubMed:7485819 ]
Shimon I, Almog S, Vered Z, Seligmann H, Shefi M, Peleg E, Rosenthal T, Motro M, Halkin H, Ezra D: Improved left ventricular function after thiamine supplementation in patients with congestive heart failure receiving long-term furosemide therapy. Am J Med. 1995 May;98(5):485-90. doi: 10.1016/s0002-9343(99)80349-0. [PubMed:7733128 ]
Lynch PL, Trimble ER, Young IS: High-performance liquid chromatographic determination of thiamine diphosphate in erythrocytes using internal standard methodology. J Chromatogr B Biomed Sci Appl. 1997 Nov 7;701(1):120-3. doi: 10.1016/s0378-4347(97)00353-8. [PubMed:9389346 ]
Schenk G, Duggleby RG, Nixon PF: Properties and functions of the thiamin diphosphate dependent enzyme transketolase. Int J Biochem Cell Biol. 1998 Dec;30(12):1297-318. doi: 10.1016/s1357-2725(98)00095-8. [PubMed:9924800 ]
Talwar D, Davidson H, Cooney J, St JO'Reilly D: Vitamin B(1) status assessed by direct measurement of thiamin pyrophosphate in erythrocytes or whole blood by HPLC: comparison with erythrocyte transketolase activation assay. Clin Chem. 2000 May;46(5):704-10. [PubMed:10794754 ]
Essama-Tjani JC, Guilland JC, Fuchs F, Lombard M, Richard D: Changes in thiamin, riboflavin, niacin, beta-carotene, vitamins, C, A, D and E status of French Elderly Subjects during the first year of institutionalization. Int J Vitam Nutr Res. 2000 Mar;70(2):54-64. doi: 10.1024/0300-9831.70.2.54. [PubMed:10804457 ]
Frank T, Bitsch R, Maiwald J, Stein G: High thiamine diphosphate concentrations in erythrocytes can be achieved in dialysis patients by oral administration of benfontiamine. Eur J Clin Pharmacol. 2000 Jun;56(3):251-7. doi: 10.1007/s002280000131. [PubMed:10952481 ]
Winston AP, Jamieson CP, Madira W, Gatward NM, Palmer RL: Prevalence of thiamin deficiency in anorexia nervosa. Int J Eat Disord. 2000 Dec;28(4):451-4. doi: 10.1002/1098-108x(200012)28:4<451::aid-eat14>3.0.co;2-i. [PubMed:11054793 ]
Singleton CK, Martin PR: Molecular mechanisms of thiamine utilization. Curr Mol Med. 2001 May;1(2):197-207. doi: 10.2174/1566524013363870. [PubMed:11899071 ]
Levy S, Herve C, Delacoux E, Erlinger S: Thiamine deficiency in hepatitis C virus and alcohol-related liver diseases. Dig Dis Sci. 2002 Mar;47(3):543-8. doi: 10.1023/a:1017907817423. [PubMed:11911339 ]
Molina JA, Jimenez-Jimenez FJ, Hernanz A, Fernandez-Vivancos E, Medina S, de Bustos F, Gomez-Escalonilla C, Sayed Y: Cerebrospinal fluid levels of thiamine in patients with Alzheimer's disease. J Neural Transm (Vienna). 2002 Jul;109(7-8):1035-44. doi: 10.1007/s007020200087. [PubMed:12111441 ]
Naito E, Ito M, Yokota I, Saijo T, Ogawa Y, Kuroda Y: Diagnosis and molecular analysis of three male patients with thiamine-responsive pyruvate dehydrogenase complex deficiency. J Neurol Sci. 2002 Sep 15;201(1-2):33-7. doi: 10.1016/s0022-510x(02)00187-9. [PubMed:12163191 ]
Casteels M, Foulon V, Mannaerts GP, Van Veldhoven PP: Alpha-oxidation of 3-methyl-substituted fatty acids and its thiamine dependence. Eur J Biochem. 2003 Apr;270(8):1619-27. doi: 10.1046/j.1432-1033.2003.03534.x. [PubMed:12694175 ]
Foulon V, Sniekers M, Huysmans E, Asselberghs S, Mahieu V, Mannaerts GP, Van Veldhoven PP, Casteels M: Breakdown of 2-hydroxylated straight chain fatty acids via peroxisomal 2-hydroxyphytanoyl-CoA lyase: a revised pathway for the alpha-oxidation of straight chain fatty acids. J Biol Chem. 2005 Mar 18;280(11):9802-12. doi: 10.1074/jbc.M413362200. Epub 2005 Jan 11. [PubMed:15644336 ]

Showing metabocard for Thiamine pyrophosphate (MMDBc0029635)

MOL for #<Metabolite:0x00007fdb07c90e20>

3D MOL for #<Metabolite:0x00007fdb07c90e20>

3D SDF for #<Metabolite:0x00007fdb07c90e20>

3D-SDF for #<Metabolite:0x00007fdb07c90e20>

PDB for #<Metabolite:0x00007fdb07c90e20>

3D PDB for #<Metabolite:0x00007fdb07c90e20>

SMILES for #<Metabolite:0x00007fdb07c90e20>

INCHI for #<Metabolite:0x00007fdb07c90e20>

Structure for #<Metabolite:0x00007fdb07c90e20>

3D Structure for #<Metabolite:0x00007fdb07c90e20>