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enzymes (17) Show 17 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-07 16:45:29 UTC

HMDB ID

HMDB0001372

Secondary Accession Numbers

HMDB0062636
HMDB01372
HMDB62636

Metabolite Identification

Common Name

Thiamine pyrophosphate

Description

Thiamine pyrophosphate (CAS: 154-87-0) is the active form of thiamine, and it serves as a cofactor for several enzymes involved primarily in carbohydrate catabolism. These enzymes are important in the biosynthesis of several cell constituents, including neurotransmitters, and for the production of reducing equivalents used in oxidant stress defences. The enzymes are also important for the 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 catalyze reactions that 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 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 the formation of a second carbanion (enamine). This formation 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 a cofactor. The thiamine pyrophosphate dependence of the third step is unique in peroxisomal mammalian enzymology. Human pathology due to a deficient alpha-oxidation is mostly linked to mutations in the gene coding for the second enzyme of the sequence, phytanoyl-CoA hydroxylase (EC 1.14.11.18) (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>
HMDB0001372

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₁₂H₁₉N₄O₇P₂S

Average Molecular Weight

425.314

Monoisotopic Molecular Weight

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

136-09-4

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 )

Ontology

Physiological effect

Adverse health effect

Genetic disorder

Inborn errors of metabolism

Nontypified gene mutations

Organic acidemia

3-hydroxy-3-methylglutaryl-coa lyase deficiency
3-hydroxyisobutyric aciduria
Beta-ketothiolase deficiency

Fumarase deficiency (PMID: 24182348 , PMID: 24182348 , PMID: 26078636 , +28

Source	Link
Pubmed	PMID: 24182348
Pubmed	PMID: 24182348
Pubmed	PMID: 26078636
Pubmed	PMID: 4837567
Pubmed	PMID: 14708889
Pubmed	PMID: 8087979
Pubmed	PMID: 26078636
Pubmed	PMID: 12383482
Pubmed	PMID: 31963255
Pubmed	PMID: 12376931
Pubmed	PMID: 2026685
Pubmed	PMID: 6616883
Pubmed	PMID: 16972175
Pubmed	PMID: 18953024
Pubmed	PMID: 2242313
Pubmed	PMID: 3571488
Pubmed	PMID: 7776094
Pubmed	PMID: 21910240
Pubmed	PMID: 28070528
Pubmed	PMID: 22308371
Pubmed	PMID: 24023812
Pubmed	PMID: 27012787
Pubmed	PMID: 9573551
Pubmed	PMID: 27504266
Pubmed	PMID: 30817767
Pubmed	PMID: 1640293
Pubmed	PMID: 25012580
Pubmed	PMID: 21389975
Pubmed	PMID: 11067816
Pubmed	PMID: 21388201
Pubmed	PMID: 24341803

)

Isovaleric acidemia (PMID: 2000815 , PMID: 9368807 , PMID: 14608088 , +33

Source	Link
Pubmed	PMID: 2000815
Pubmed	PMID: 9368807
Pubmed	PMID: 14608088
Pubmed	PMID: 8412012
Pubmed	PMID: 21359215
Pubmed	PMID: 24740205
Pubmed	PMID: 18953024
Pubmed	PMID: 32966057
Pubmed	PMID: 20671299
Pubmed	PMID: 27329611
Pubmed	PMID: 27329611
Pubmed	PMID: 1246461
Pubmed	PMID: 1246461
Pubmed	PMID: 24023812
Pubmed	PMID: 11978597
Pubmed	PMID: 17069347
Pubmed	PMID: 17313719
Pubmed	PMID: 21185973
Pubmed	PMID: 18633173
Pubmed	PMID: 27355821
Pubmed	PMID: 10022638
Pubmed	PMID: 18203893
Pubmed	PMID: 24801555
Pubmed	PMID: 11593343
Pubmed	PMID: 10197568
Pubmed	PMID: 7609451
Pubmed	PMID: 12837870
Pubmed	PMID: 12837870
Pubmed	PMID: 25004141
Pubmed	PMID: 20143319
Pubmed	PMID: 14634727
Pubmed	PMID: 2361977
Pubmed	PMID: 18953024
Pubmed	PMID: 24789758
Pubmed	PMID: 22007635
Pubmed	PMID: 22061338

)

Malonyl-coa decarboxylase deficiency

Maple syrup urine disease (PMID: 24023812 , PMID: 6321058 , PMID: 20971021 , +59

Source	Link
Pubmed	PMID: 24023812
Pubmed	PMID: 6321058
Pubmed	PMID: 20971021
Pubmed	PMID: 20573794
Pubmed	PMID: 23657156
Pubmed	PMID: 22800120
Pubmed	PMID: 21389975
Pubmed	PMID: 27012787
Pubmed	PMID: 9625050
Pubmed	PMID: 15740018
Pubmed	PMID: 12663291
Pubmed	PMID: 2702744
Pubmed	PMID: 16939360
Pubmed	PMID: 17474139
Pubmed	PMID: 15992788
Pubmed	PMID: 22827565
Pubmed	PMID: 22148915
Pubmed	PMID: 21388201
Pubmed	PMID: 22932811
Pubmed	PMID: 19551947
Pubmed	PMID: 31775291
Pubmed	PMID: 2026685
Pubmed	PMID: 4434100
Pubmed	PMID: 28853722
Pubmed	PMID: 19033659
Pubmed	PMID: 23430553
Pubmed	PMID: 3168222
Pubmed	PMID: 19468821
Pubmed	PMID: 31506554
Pubmed	PMID: 19309105
Pubmed	PMID: 17022649
Pubmed	PMID: 25733631
Pubmed	PMID: 32966057
Pubmed	PMID: 25536744
Pubmed	PMID: 15651030
Pubmed	PMID: 24909877
Pubmed	PMID: 6422161
Pubmed	PMID: 10102904
Pubmed	PMID: 21736852
Pubmed	PMID: 17349089
Pubmed	PMID: 16601883
Pubmed	PMID: 9246418
Pubmed	PMID: 25012580
Pubmed	PMID: 25213569
Pubmed	PMID: 5727921
Pubmed	PMID: 5472370
Pubmed	PMID: 30830347
Pubmed	PMID: 18088602
Pubmed	PMID: 22956686
Pubmed	PMID: 27294788
Pubmed	PMID: 18088602
Pubmed	PMID: 19217890
Pubmed	PMID: 9732980
Pubmed	PMID: 18004736
Pubmed	PMID: 11052553
Pubmed	PMID: 15899597
Pubmed	PMID: 5018656
Pubmed	PMID: 21505807
Pubmed	PMID: 25754623
Pubmed	PMID: 6422161
Pubmed	PMID: 23430924
Pubmed	PMID: 10508118

)

Propionic acidemia (PMID: 24023812 , PMID: 6321058 , PMID: 20971021 , +65

Source	Link
Pubmed	PMID: 24023812
Pubmed	PMID: 6321058
Pubmed	PMID: 20971021
Pubmed	PMID: 20573794
Pubmed	PMID: 23657156
Pubmed	PMID: 22800120
Pubmed	PMID: 21389975
Pubmed	PMID: 27012787
Pubmed	PMID: 9625050
Pubmed	PMID: 15740018
Pubmed	PMID: 12663291
Pubmed	PMID: 2702744
Pubmed	PMID: 16939360
Pubmed	PMID: 17474139
Pubmed	PMID: 15992788
Pubmed	PMID: 22827565
Pubmed	PMID: 22148915
Pubmed	PMID: 21388201
Pubmed	PMID: 22932811
Pubmed	PMID: 19551947
Pubmed	PMID: 31775291
Pubmed	PMID: 2026685
Pubmed	PMID: 4434100
Pubmed	PMID: 28853722
Pubmed	PMID: 19033659
Pubmed	PMID: 23430553
Pubmed	PMID: 3168222
Pubmed	PMID: 19468821
Pubmed	PMID: 31506554
Pubmed	PMID: 17022649
Pubmed	PMID: 25733631
Pubmed	PMID: 32966057
Pubmed	PMID: 19309105
Pubmed	PMID: 25536744
Pubmed	PMID: 23062437
Pubmed	PMID: 21704015
Pubmed	PMID: 28853722
Pubmed	PMID: 23705938
Pubmed	PMID: 15651030
Pubmed	PMID: 24909877
Pubmed	PMID: 2226555
Pubmed	PMID: 6616873
Pubmed	PMID: 10102904
Pubmed	PMID: 21736852
Pubmed	PMID: 17349089
Pubmed	PMID: 16601883
Pubmed	PMID: 9246418
Pubmed	PMID: 9667231
Pubmed	PMID: 21841779
Pubmed	PMID: 9439441
Pubmed	PMID: 11067816
Pubmed	PMID: 16139832
Pubmed	PMID: 25012580
Pubmed	PMID: 25213569
Pubmed	PMID: 5727921
Pubmed	PMID: 5472370
Pubmed	PMID: 30830347
Pubmed	PMID: 28028301
Pubmed	PMID: 9187477
Pubmed	PMID: 26910390
Pubmed	PMID: 7131143
Pubmed	PMID: 19217890
Pubmed	PMID: 9732980
Pubmed	PMID: 8087979
Pubmed	PMID: 23269817
Pubmed	PMID: 15899597
Pubmed	PMID: 11052553
Pubmed	PMID: 18004736

)

Nervous system disorder

Central nervous system disorder

Alzheimer's disease (PMID: 23857558 , PMID: 22308371 , PMID: 23857558 , +173

Source	Link
Pubmed	PMID: 23857558
Pubmed	PMID: 22308371
Pubmed	PMID: 23857558
Pubmed	PMID: 11310987
Pubmed	PMID: 16244393
Pubmed	PMID: 12111441
Pubmed	PMID: 12111441
Pubmed	PMID: 21164041
Pubmed	PMID: 19259987
Pubmed	PMID: 12097436
Pubmed	PMID: 20300169
Pubmed	PMID: 22194922
Pubmed	PMID: 26755145
Pubmed	PMID: 17031479
Pubmed	PMID: 27355821
Pubmed	PMID: 12297216
Pubmed	PMID: 32966057
Pubmed	PMID: 25037050
Pubmed	PMID: 19468821
Pubmed	PMID: 27012787
Pubmed	PMID: 3168222
Pubmed	PMID: 19033659
Pubmed	PMID: 15723447
Pubmed	PMID: 8595727
Pubmed	PMID: 8595727
Pubmed	PMID: 21113737
Pubmed	PMID: 17068770
Pubmed	PMID: 15911239
Pubmed	PMID: 6198473
Pubmed	PMID: 22546835
Pubmed	PMID: 7595563
Pubmed	PMID: 20803002
Pubmed	PMID: 6321058
Pubmed	PMID: 31775291
Pubmed	PMID: 22800120
Pubmed	PMID: 2026685
Pubmed	PMID: 4434100
Pubmed	PMID: 28853722
Pubmed	PMID: 23430553
Pubmed	PMID: 17474139
Pubmed	PMID: 24023812
Pubmed	PMID: 31506554
Pubmed	PMID: 24341803
Pubmed	PMID: 12834252
Pubmed	PMID: 21389975
Pubmed	PMID: 15061359
Pubmed	PMID: 18502700
Pubmed	PMID: 22727327
Pubmed	PMID: 20300169
Pubmed	PMID: 28157703
Pubmed	PMID: 20549362
Pubmed	PMID: 30830347
Pubmed	PMID: 21388201
Pubmed	PMID: 19754154
Pubmed	PMID: 18953024
Pubmed	PMID: 1268322
Pubmed	PMID: 24246267
Pubmed	PMID: 21190195
Pubmed	PMID: 16244393
Pubmed	PMID: 25536744
Pubmed	PMID: 15531511
Pubmed	PMID: 22944140
Pubmed	PMID: 26161337
Pubmed	PMID: 8187312
Pubmed	PMID: 27543620
Pubmed	PMID: 8478958
Pubmed	PMID: 7710082
Pubmed	PMID: 15361288
Pubmed	PMID: 15361288
Pubmed	PMID: 11419735
Pubmed	PMID: 3757213
Pubmed	PMID: 15465626
Pubmed	PMID: 16244395
Pubmed	PMID: 22932811
Pubmed	PMID: 19309105
Pubmed	PMID: 15992788
Pubmed	PMID: 9367221
Pubmed	PMID: 16244392
Pubmed	PMID: 9693263
Pubmed	PMID: 9720975
Pubmed	PMID: 21736852
Pubmed	PMID: 10102904
Pubmed	PMID: 8412012
Pubmed	PMID: 8448848
Pubmed	PMID: 21841779
Pubmed	PMID: 8345822
Pubmed	PMID: 11067816
Pubmed	PMID: 8356878
Pubmed	PMID: 16227558
Pubmed	PMID: 10840171
Pubmed	PMID: 21359215
Pubmed	PMID: 16635166
Pubmed	PMID: 22892715
Pubmed	PMID: 4122112
Pubmed	PMID: 28278231
Pubmed	PMID: 27294788
Pubmed	PMID: 7623444
Pubmed	PMID: 5472370
Pubmed	PMID: 5727921
Pubmed	PMID: 16087168
Pubmed	PMID: 22024767
Pubmed	PMID: 12391605
Pubmed	PMID: 12391605
Pubmed	PMID: 2311630
Pubmed	PMID: 624188
Pubmed	PMID: 7108550
Pubmed	PMID: 23890588
Pubmed	PMID: 31026179
Pubmed	PMID: 10588400
Pubmed	PMID: 10662965
Pubmed	PMID: 14710103
Pubmed	PMID: 14992292
Pubmed	PMID: 15145598
Pubmed	PMID: 21292280
Pubmed	PMID: 9720975
Pubmed	PMID: 18953024
Pubmed	PMID: 23940645
Pubmed	PMID: 28028301
Pubmed	PMID: 9187477
Pubmed	PMID: 9187477
Pubmed	PMID: 14680976
Pubmed	PMID: 14744923
Pubmed	PMID: 15921697
Pubmed	PMID: 28270806
Pubmed	PMID: 27609529
Pubmed	PMID: 27624970
Pubmed	PMID: 29808030
Pubmed	PMID: 25733631
Pubmed	PMID: 27912044
Pubmed	PMID: 1641639
Pubmed	PMID: 19289823
Pubmed	PMID: 16895893
Pubmed	PMID: 14750096
Pubmed	PMID: 4031843
Pubmed	PMID: 10494443
Pubmed	PMID: 9849813
Pubmed	PMID: 2026685
Pubmed	PMID: 11959400
Pubmed	PMID: 20087382
Pubmed	PMID: 21474939
Pubmed	PMID: 11959400
Pubmed	PMID: 7164933
Pubmed	PMID: 7711000
Pubmed	PMID: 20932951
Pubmed	PMID: 20858978
Pubmed	PMID: 1716470
Pubmed	PMID: 17384003
Pubmed	PMID: 16227558
Pubmed	PMID: 15711082
Pubmed	PMID: 894411
Pubmed	PMID: 22007635
Pubmed	PMID: 25004141
Pubmed	PMID: 19678709
Pubmed	PMID: 19390223
Pubmed	PMID: 24027187
Pubmed	PMID: 6182788
Pubmed	PMID: 11383938
Pubmed	PMID: 2580417
Pubmed	PMID: 17031479
Pubmed	PMID: 23269817
Pubmed	PMID: 15899597
Pubmed	PMID: 11052553
Pubmed	PMID: 1931558
Pubmed	PMID: 24341803
Pubmed	PMID: 16267323
Pubmed	PMID: 18004736
Pubmed	PMID: 23896378
Pubmed	PMID: 12663078
Pubmed	PMID: 21190195
Pubmed	PMID: 22024767
Pubmed	PMID: 6161319
Pubmed	PMID: 2581184
Pubmed	PMID: 9413017
Pubmed	PMID: 11314776
Pubmed	PMID: 8945737
Pubmed	PMID: 11314776

)

Disposition

Biological location

Cellular substructure

Cytoplasm

Non-excretory biofluid

Blood

Organ

Brain

Cell

Hematocyte

Erythrocyte

Green lentil

Other pulses

Peas

Lentils

Lentils

Onion-family vegetables

Herb and spice mixtures

Curry powder

Cereals and cereal products

Cereals

Cereal products

Doughs

Sourdough

Leavened breads

Flat breads

Other breads

Potato bread

Sweet breads

Raisin bread

Teas

Herbal tea

Herbal teas

Taco shell
Tostada shell

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Coffee and coffee products

Coffee

Soy

Soy products

Soy bean

Baking goods

Wrappers

Wonton wrapper

Process

Naturally occurring process

Warburg effect

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 Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	192.269	31661259
DarkChem	[M+H]+	192.269	31661259
DarkChem	[M-H]-	185.88	31661259
DarkChem	[M-H]-	185.88	31661259
AllCCS	[M+H]+	189.355	32859911
AllCCS	[M-H]-	184.184	32859911
DeepCCS	[M+H]+	156.089	30932474
DeepCCS	[M-H]-	153.73	30932474
DeepCCS	[M-2H]-	188.093	30932474
DeepCCS	[M+Na]+	163.603	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thiamine pyrophosphate	CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N	4652.2	Standard polar	33892256
Thiamine pyrophosphate	CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N	2938.3	Standard non polar	33892256
Thiamine pyrophosphate	CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N	3548.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thiamine pyrophosphate,1TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N)=N1	3503.0	Semi standard non polar	33892256
Thiamine pyrophosphate,1TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N)=N1	3175.9	Standard non polar	33892256
Thiamine pyrophosphate,1TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N)=N1	5436.9	Standard polar	33892256
Thiamine pyrophosphate,1TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N1	3473.5	Semi standard non polar	33892256
Thiamine pyrophosphate,1TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N1	3183.1	Standard non polar	33892256
Thiamine pyrophosphate,1TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N1	5440.4	Standard polar	33892256
Thiamine pyrophosphate,1TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N1	3545.2	Semi standard non polar	33892256
Thiamine pyrophosphate,1TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N1	3132.4	Standard non polar	33892256
Thiamine pyrophosphate,1TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N1	5580.9	Standard polar	33892256
Thiamine pyrophosphate,2TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N1	3448.3	Semi standard non polar	33892256
Thiamine pyrophosphate,2TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N1	3261.7	Standard non polar	33892256
Thiamine pyrophosphate,2TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N1	4938.9	Standard polar	33892256
Thiamine pyrophosphate,2TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N1	3491.8	Semi standard non polar	33892256
Thiamine pyrophosphate,2TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N1	3221.0	Standard non polar	33892256
Thiamine pyrophosphate,2TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N1	4922.4	Standard polar	33892256
Thiamine pyrophosphate,2TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N1	3450.9	Semi standard non polar	33892256
Thiamine pyrophosphate,2TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N1	3248.6	Standard non polar	33892256
Thiamine pyrophosphate,2TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N1	5009.9	Standard polar	33892256
Thiamine pyrophosphate,2TMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3475.6	Semi standard non polar	33892256
Thiamine pyrophosphate,2TMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3215.5	Standard non polar	33892256
Thiamine pyrophosphate,2TMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	4982.7	Standard polar	33892256
Thiamine pyrophosphate,2TMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3481.8	Semi standard non polar	33892256
Thiamine pyrophosphate,2TMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3273.0	Standard non polar	33892256
Thiamine pyrophosphate,2TMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	5171.3	Standard polar	33892256
Thiamine pyrophosphate,3TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N1	3454.0	Semi standard non polar	33892256
Thiamine pyrophosphate,3TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N1	3266.2	Standard non polar	33892256
Thiamine pyrophosphate,3TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N1	4610.5	Standard polar	33892256
Thiamine pyrophosphate,3TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3485.2	Semi standard non polar	33892256
Thiamine pyrophosphate,3TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3272.1	Standard non polar	33892256
Thiamine pyrophosphate,3TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	4506.9	Standard polar	33892256
Thiamine pyrophosphate,3TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3477.0	Semi standard non polar	33892256
Thiamine pyrophosphate,3TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3326.5	Standard non polar	33892256
Thiamine pyrophosphate,3TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	4610.1	Standard polar	33892256
Thiamine pyrophosphate,3TMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3482.1	Semi standard non polar	33892256
Thiamine pyrophosphate,3TMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3262.6	Standard non polar	33892256
Thiamine pyrophosphate,3TMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	4529.7	Standard polar	33892256
Thiamine pyrophosphate,3TMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3463.1	Semi standard non polar	33892256
Thiamine pyrophosphate,3TMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3312.6	Standard non polar	33892256
Thiamine pyrophosphate,3TMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	4683.2	Standard polar	33892256
Thiamine pyrophosphate,4TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3513.2	Semi standard non polar	33892256
Thiamine pyrophosphate,4TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	3285.2	Standard non polar	33892256
Thiamine pyrophosphate,4TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N1	4088.4	Standard polar	33892256
Thiamine pyrophosphate,4TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3478.8	Semi standard non polar	33892256
Thiamine pyrophosphate,4TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3332.0	Standard non polar	33892256
Thiamine pyrophosphate,4TMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	4223.5	Standard polar	33892256
Thiamine pyrophosphate,4TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3479.3	Semi standard non polar	33892256
Thiamine pyrophosphate,4TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3324.3	Standard non polar	33892256
Thiamine pyrophosphate,4TMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	4224.2	Standard polar	33892256
Thiamine pyrophosphate,5TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3504.4	Semi standard non polar	33892256
Thiamine pyrophosphate,5TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3319.7	Standard non polar	33892256
Thiamine pyrophosphate,5TMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N1	3837.3	Standard polar	33892256
Thiamine pyrophosphate,1TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N)=N1	3736.9	Semi standard non polar	33892256
Thiamine pyrophosphate,1TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N)=N1	3366.3	Standard non polar	33892256
Thiamine pyrophosphate,1TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N)=N1	5511.0	Standard polar	33892256
Thiamine pyrophosphate,1TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	3717.0	Semi standard non polar	33892256
Thiamine pyrophosphate,1TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	3374.5	Standard non polar	33892256
Thiamine pyrophosphate,1TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	5512.0	Standard polar	33892256
Thiamine pyrophosphate,1TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3753.6	Semi standard non polar	33892256
Thiamine pyrophosphate,1TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3320.7	Standard non polar	33892256
Thiamine pyrophosphate,1TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	5517.7	Standard polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	3885.9	Semi standard non polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	3589.6	Standard non polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	5068.7	Standard polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3917.6	Semi standard non polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3560.9	Standard non polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	5029.9	Standard polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	3892.3	Semi standard non polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	3570.3	Standard non polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	5136.8	Standard polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3898.2	Semi standard non polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3564.3	Standard non polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	5084.8	Standard polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3907.4	Semi standard non polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3623.4	Standard non polar	33892256
Thiamine pyrophosphate,2TBDMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	5165.0	Standard polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	4028.8	Semi standard non polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	3691.5	Standard non polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N1	4751.5	Standard polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	4056.0	Semi standard non polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3734.6	Standard non polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	4680.4	Standard polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	4076.7	Semi standard non polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3793.5	Standard non polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	4749.9	Standard polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	4059.4	Semi standard non polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3717.1	Standard non polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #4	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	4711.6	Standard polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	4056.5	Semi standard non polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3792.1	Standard non polar	33892256
Thiamine pyrophosphate,3TBDMS,isomer #5	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	4817.1	Standard polar	33892256
Thiamine pyrophosphate,4TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	4233.1	Semi standard non polar	33892256
Thiamine pyrophosphate,4TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	3834.5	Standard non polar	33892256
Thiamine pyrophosphate,4TBDMS,isomer #1	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N[Si](C)(C)C(C)(C)C)=N1	4337.3	Standard polar	33892256
Thiamine pyrophosphate,4TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	4224.2	Semi standard non polar	33892256
Thiamine pyrophosphate,4TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3900.4	Standard non polar	33892256
Thiamine pyrophosphate,4TBDMS,isomer #2	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	4409.0	Standard polar	33892256
Thiamine pyrophosphate,4TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	4225.4	Semi standard non polar	33892256
Thiamine pyrophosphate,4TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	3879.3	Standard non polar	33892256
Thiamine pyrophosphate,4TBDMS,isomer #3	CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C2C)C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=N1	4428.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamine pyrophosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-9734000000-83738512818790cf1cc5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamine pyrophosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004i-0201900000-9ca110d3800e4ebfad43	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00di-0900000000-dad8835a4b26b1df86c4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-00di-2900000000-83b0eb52fe05e7097aff	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-00di-0000900000-538ee08c2fc9a905eaad	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0udi-0309000000-b196fd5684e86907d04e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0udi-0409000000-088cf88d5056ce245770	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-004i-9822000000-011b97ebb9fdcebffc93	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-004i-9200000000-2ecd5ee7eb283c5cd990	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-004i-0001900000-59ea8d394aed62700202	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-00b9-0614900000-08f09a377f03019f4457	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-00di-0911000000-de2b56b98b01c6409b09	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-00di-0900000000-7d75ca5105912446e47b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-00di-2900000000-d632b8688f17a7a01de0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , negative-QTOF	splash10-00di-0000900000-538ee08c2fc9a905eaad	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , negative-QTOF	splash10-0udi-0309000000-b196fd5684e86907d04e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , negative-QTOF	splash10-0udi-0409000000-088cf88d5056ce245770	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , negative-QTOF	splash10-004i-9822000000-670f784e69ef56047333	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , negative-QTOF	splash10-004i-9200000000-2ecd5ee7eb283c5cd990	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , positive-QTOF	splash10-004i-0001900000-59ea8d394aed62700202	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine pyrophosphate 10V, Positive-QTOF	splash10-004i-0100900000-2d5d6c77c0c7e2d2d28a	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine pyrophosphate 20V, Positive-QTOF	splash10-0aba-8146900000-e4efbc495cf0eb380395	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine pyrophosphate 40V, Positive-QTOF	splash10-0a4j-4911100000-7e4a6eda3f297e8051b7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine pyrophosphate 10V, Negative-QTOF	splash10-00di-0000900000-08198f6dfeaa404b8b0f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine pyrophosphate 20V, Negative-QTOF	splash10-001i-9100200000-2d9e7e5d87267ce83dcc	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamine pyrophosphate 40V, Negative-QTOF	splash10-004j-9200000000-a470e5de9f124c159e0e	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

Tissue Locations

Brain
Erythrocyte
Fibroblasts

Pathways

Name	SMPDB/PathBank	KEGG
Thiamine Metabolism
Valine, leucine and isoleucine degradation	Not Available
Citric Acid Cycle
Congenital lactic acidosis		Not Available
Fumarase deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0032 +/- 0.0022 uM	Adult (>18 years old)	Both	Normal	12111441	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.034 (0-0.066) uM	Adult (>18 years old)	Not Specified	Cerebrocortical Degeneration	17642321	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0025 +/- 0.0017 uM	Adult (>18 years old)	Both	Alzheimer's disease	12111441	details

Associated Disorders and Diseases

Disease References

Cerebrocortical degeneration
Holtershinken M, Hohling A, Witte B, Scholz H: [Thiamine and its derivates in cattle blood measured by HPLC in healthy animals, in patients suffering from CCN and in their cohorts]. Dtsch Tierarztl Wochenschr. 2007 Jun;114(6):212-8. [PubMed:17642321 ]
Alzheimer's disease
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. [PubMed:12111441 ]

Associated OMIM IDs

104300 (Alzheimer's disease)

External Links

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

VMH ID

THMPP

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Zabrodskaya, S. V.; Oparin, D. A.; Ostrovskii, Yu. M. Selective synthesis of thiamine diphosphate. Zhurnal Obshchei Khimii (1989), 59(1), 226-7.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. Epub 2005 Jan 11. [PubMed:15644336 ]
Singleton CK, Martin PR: Molecular mechanisms of thiamine utilization. Curr Mol Med. 2001 May;1(2):197-207. [PubMed:11899071 ]
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. [PubMed:12111441 ]
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. [PubMed:7733128 ]
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 ]
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. [PubMed:10804457 ]
Warnock LG: The measurement of erythrocyte thiamin pyrophosphate by high-performance liquid chromatography. Anal Biochem. 1982 Nov 1;126(2):394-7. [PubMed:7158773 ]
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. [PubMed:9389346 ]
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. [PubMed:12163191 ]
Baines M: Improved high performance liquid chromatographic determination of thiamin diphosphate in erythrocytes. Clin Chim Acta. 1985 Nov 29;153(1):43-8. [PubMed:4075519 ]
Duffy P, Morris H, Neilson G: Thiamin status of a Melanesian population. Am J Clin Nutr. 1981 Aug;34(8):1584-92. [PubMed:7270482 ]
Kjosen B, Seim SH: The transketolase assay of thiamine in some diseases. Am J Clin Nutr. 1977 Oct;30(10):1591-6. [PubMed:910736 ]
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. [PubMed:11054793 ]
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. [PubMed:11911339 ]
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 ]
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. [PubMed:3565758 ]
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. [PubMed:10952481 ]
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. [PubMed:7485819 ]
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. [PubMed:12694175 ]
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. [PubMed:9924800 ]

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Pyruvate dehydrogenase E1 component subunit beta, mitochondrial

General function:: Involved in catalytic activity
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: PDHB
Uniprot ID:: P11177
Molecular weight:: 39233.1

Reactions

Pyruvic acid + Thiamine pyrophosphate → 2-(a-Hydroxyethyl)thiamine diphosphate + Carbon dioxide	details
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphate	details

Enzyme Details

2. Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: PDHA1
Uniprot ID:: P08559
Molecular weight:: 43295.255

Reactions

Pyruvic acid + Thiamine pyrophosphate → 2-(a-Hydroxyethyl)thiamine diphosphate + Carbon dioxide	details
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphate	details

Enzyme Details

3. Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:: The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
Gene Name:: PDHA2
Uniprot ID:: P29803
Molecular weight:: 42932.855

Reactions

Pyruvic acid + Thiamine pyrophosphate → 2-(a-Hydroxyethyl)thiamine diphosphate + Carbon dioxide	details
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphate	details

Enzyme Details

4. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial

General function:: Involved in catalytic activity
Specific function:: The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:: BCKDHB
Uniprot ID:: P21953
Molecular weight:: 43122.065

Reactions

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

Enzyme Details

5. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial

General function:: Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:: The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:: BCKDHA
Uniprot ID:: P12694
Molecular weight:: 50470.58

Reactions

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

Enzyme Details

6. 2-oxoglutarate dehydrogenase, mitochondrial

General function:: Involved in oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:: The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components: 2-oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:: OGDH
Uniprot ID:: Q02218
Molecular weight:: 48179.59

Reactions

Oxoglutaric acid + Thiamine pyrophosphate → 3-Carboxy-1-hydroxypropylthiamine diphosphate + Carbon dioxide	details
3-Carboxy-1-hydroxypropylthiamine diphosphate + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine + Thiamine pyrophosphate	details

Enzyme Details

7. Thiamin pyrophosphokinase 1

General function:: Involved in thiamin diphosphokinase activity
Specific function:: Catalyzes the phosphorylation of thiamine to thiamine pyrophosphate. Can also catalyze the phosphorylation of pyrithiamine to pyrithiamine pyrophosphate.
Gene Name:: TPK1
Uniprot ID:: Q9H3S4
Molecular weight:: 27265.05

Reactions

Adenosine triphosphate + Thiamine → Adenosine monophosphate + Thiamine pyrophosphate	details
Adenosine triphosphate + Thiamine pyrophosphate → ADP + Thiamine triphosphate	details

Enzyme Details

8. Transketolase-like protein 1

General function:: Involved in catalytic activity
Specific function:: Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate (By similarity).
Gene Name:: TKTL1
Uniprot ID:: P51854
Molecular weight:: 59302.195

Enzyme Details

9. Transketolase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:: TKT
Uniprot ID:: P29401
Molecular weight:: 67876.95

Enzyme Details

10. Ectonucleoside triphosphate diphosphohydrolase 5

General function:: Involved in hydrolase activity
Specific function:: Uridine diphosphatase (UDPase) that promotes protein N-glycosylation and ATP level regulation. UDP hydrolysis promotes protein N-glycosylation and folding in the endoplasmic reticulum, as well as elevated ATP consumption in the cytosol via an ATP hydrolysis cycle. Together with CMPK1 and AK1, constitutes an ATP hydrolysis cycle that converts ATP to AMP and results in a compensatory increase in aerobic glycolysis. Also hydrolyzes GDP and IDP but not any other nucleoside di-, mono- or triphosphates, nor thiamine pyrophosphate. Plays a key role in the AKT1-PTEN signaling pathway by promoting glycolysis in proliferating cells in response to phosphoinositide 3-kinase (PI3K) signaling (By similarity).
Gene Name:: ENTPD5
Uniprot ID:: O75356
Molecular weight:: 47516.985

Only showing the first 10 proteins. There are 17 proteins in total.

Show all enzymes and transporters

Showing metabocard for Thiamine pyrophosphate (HMDB0001372)

MOL for HMDB0001372 (Thiamine pyrophosphate)

3D MOL for HMDB0001372 (Thiamine pyrophosphate)

3D SDF for HMDB0001372 (Thiamine pyrophosphate)

3D-SDF for HMDB0001372 (Thiamine pyrophosphate)

PDB for HMDB0001372 (Thiamine pyrophosphate)

3D PDB for HMDB0001372 (Thiamine pyrophosphate)

SMILES for HMDB0001372 (Thiamine pyrophosphate)

INCHI for HMDB0001372 (Thiamine pyrophosphate)

Structure for HMDB0001372 (Thiamine pyrophosphate)

3D Structure for HMDB0001372 (Thiamine pyrophosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions