NP-MRD: Showing NP-Card for Thiamine pyrophosphate (NP0001077)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-06-29 00:47:02 UTC

NP-MRD ID

NP0001077

Secondary Accession Numbers

None

Natural Product 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>
NP0001077

> <DATABASE_NAME>
NP-MRD

> <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

Synonyms

Value	Source
3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)thiazolium	ChEBI
3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium	ChEBI
THDP	ChEBI
Thiamin diphosphate	ChEBI
Thiamin pyrophosphate	ChEBI
Thiamine diphosphate	ChEBI
Thiamine-pyrophosphate	ChEBI
THPP	ChEBI
TPP	ChEBI
Thiamin diphosphoric acid	Generator
Thiamin pyrophosphoric acid	Generator
Thiamine diphosphoric acid	Generator
Thiamine-pyrophosphoric acid	Generator
Thiamine pyrophosphoric acid	Generator
Thaimine pyrophosphate	HMDB
Thiamin-ppi	HMDB
Thiamine-ppi	HMDB
Cocarboxylase	HMDB
Berolase	HMDB
Pyrophosphate, thiamine	HMDB

Chemical Formula

C₁₂H₁₉N₄O₇P₂S

Average Mass

425.3140 Da

Monoisotopic Mass

425.04497 Da

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(CCO[P@](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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	Varshavi.d26			2021-09-06	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Varshavi.d26			2021-09-06	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, simulated)	Varshavi.d26			2021-08-16	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus esculentus	FooDB	FooDB
Actinidia chinensis	FooDB	FooDB
Agaricus bisporus	FooDB	FooDB
Agave	FooDB	FooDB
Allium ampeloprasum	FooDB	FooDB
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	FooDB
Allium cepa L.	FooDB	FooDB
Allium fistulosum	FooDB	FooDB
Allium sativum	FooDB	FooDB
Allium schoenoprasum	FooDB	FooDB
Allium tuberosum	FooDB	FooDB
Aloysia triphylla	FooDB	FooDB
Amaranthus	FooDB	FooDB
Amelanchier alnifolia	FooDB	FooDB
Anacardium occidentale	FooDB	FooDB
Ananas comosus	FooDB	FooDB
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anethum graveolens	FooDB	FooDB
Angelica keiskei	FooDB	FooDB
Annona cherimola	FooDB	FooDB
Annona muricata	FooDB	FooDB
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	FooDB
Anser anser	FooDB	FooDB
Anthriscus cerefolium	FooDB	FooDB
Apium graveolens	FooDB	FooDB
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	FooDB
Apium graveolens var. secalinum	FooDB	FooDB
Arachis hypogaea	FooDB	FooDB
Arctium lappa	FooDB	FooDB
Armoracia rusticana	FooDB	FooDB
Artemisia dracunculus	FooDB	FooDB
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	FooDB
Artocarpus heterophyllus	FooDB	FooDB
Asparagus officinalis	FooDB	FooDB
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Avena sativa L.	FooDB	FooDB
Averrhoa carambola	FooDB	FooDB
Basella alba	FooDB	FooDB
Benincasa hispida	FooDB	FooDB
Bertholletia excelsa	FooDB	FooDB
Beta vulgaris	FooDB	FooDB
Beta vulgaris ssp. cicla	FooDB	FooDB
Bison bison	FooDB	FooDB
Borago officinalis	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	FooDB
Brassica napus var. napus	FooDB	FooDB
Brassica oleracea	FooDB	FooDB
Brassica oleracea var. botrytis	FooDB	FooDB
Brassica oleracea var. capitata	FooDB	FooDB
Brassica oleracea var. gemmifera	FooDB	FooDB
Brassica oleracea var. gongylodes	FooDB	FooDB
Brassica oleracea var. italica	FooDB	FooDB
Brassica oleracea var. sabauda	FooDB	FooDB
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	FooDB
Brassica rapa ssp. chinensis	FooDB	FooDB
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	FooDB
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	FooDB
Canarium ovatum	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	FooDB
Capparis spinosa	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	FooDB
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	FooDB
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya L.	FooDB	FooDB
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	FooDB
Carum carvi	FooDB	FooDB
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	FooDB
Castanea	FooDB	FooDB
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Ceratonia siliqua	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chamaemelum nobile	FooDB	FooDB
Chamerion angustifolium	FooDB	FooDB
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chrysanthemum coronarium	FooDB	FooDB
Cicer arietinum	FooDB	FooDB
Cichorium endivia	FooDB	FooDB
Cichorium intybus	FooDB	FooDB
Cinnamomum	FooDB	FooDB
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	FooDB
Citrullus lanatus	FooDB	FooDB
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	FooDB
Citrus aurantiifolia	FooDB	FooDB
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	FooDB
Citrus maxima	FooDB	FooDB
Citrus paradisi	FooDB	FooDB
Citrus reticulata	FooDB	FooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	FooDB
Cocos nucifera	FooDB	FooDB
Coffea arabica L.	FooDB	FooDB
Coffea canephora	FooDB	FooDB
Colocasia esculenta	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Corchorus olitorius	FooDB	FooDB
Coriandrum sativum L.	FooDB	FooDB
Corylus	FooDB	FooDB
Corylus avellana	FooDB	FooDB
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	FooDB
Cucumis melo	FooDB	FooDB
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus L.	FooDB	FooDB
Cucurbita	FooDB	FooDB
Cucurbita maxima	FooDB	FooDB
Cucurbita moschata	FooDB	FooDB
Cuminum cyminum	FooDB	FooDB
Curcuma longa	FooDB	FooDB
Cydonia oblonga	FooDB	FooDB
Cymbopogon citratus	FooDB	FooDB
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	FooDB
Daucus carota	FooDB	FooDB
Daucus carota ssp. sativus	FooDB	FooDB
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	FooDB
Dioscorea pentaphylla	FooDB	FooDB
Diospyros	FooDB	FooDB
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Elaeis	FooDB	FooDB
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Empetrum nigrum	FooDB	FooDB
Equus caballus	FooDB	FooDB
Eragrostis tef	FooDB	FooDB
Eriobotrya japonica	FooDB	FooDB
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Escherichia coli	Bacteria	KNApSAcK
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	FooDB
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	FooDB	FooDB
Ficus carica	FooDB	FooDB
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	FooDB
Fragaria x ananassa	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Garcinia mangostana	FooDB	FooDB
Gaylussacia baccata	FooDB	FooDB
Ginkgo biloba	FooDB	FooDB
Glycine max	FooDB	FooDB
Gossypium	FooDB	FooDB
Grifola frondosa	FooDB	FooDB
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	FooDB
Helianthus tuberosus	FooDB	FooDB
Hibiscus sabbariffa	FooDB	FooDB
Hippophae rhamnoides	FooDB	FooDB
Hordeum vulgare	FooDB	FooDB
Hyssopus officinalis L.	FooDB	FooDB
Illicium verum	FooDB	FooDB
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	FooDB
Juglans	FooDB	FooDB
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	FooDB
Juglans regia	FooDB	FooDB
Lablab purpureus	FooDB	FooDB
Lactuca sativa	FooDB	FooDB
Lagenaria siceraria	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Lens culinaris	FooDB	FooDB
Lentinus edodes	FooDB	FooDB
Lepidium sativum	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Levisticum officinale	FooDB	FooDB
Linum usitatissimum	FooDB	FooDB
Litchi chinensis	FooDB	FooDB
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	FooDB
Macadamia	FooDB	FooDB
Macadamia tetraphylla	FooDB	FooDB
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	FooDB
Malus pumila	FooDB	FooDB
Mammea americana	FooDB	FooDB
Mangifera indica	FooDB	FooDB
Manihot esculenta	FooDB	FooDB
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	FooDB
Matricaria recutita	FooDB	FooDB
Matteuccia struthiopteris	FooDB	FooDB
Medicago sativa	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Melissa officinalis L.	FooDB	FooDB
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	FooDB
Mentha x piperita	FooDB	FooDB
Mespilus germanica	FooDB	FooDB
Metroxylon sagu	FooDB	FooDB
Momordica charantia	FooDB	FooDB
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Moringa oleifera	FooDB	FooDB
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Musa acuminata	FooDB	FooDB
Musa x paradisiaca	FooDB	FooDB
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	FooDB
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	FooDB
Nephelium lappaceum	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Nuphar lutea	FooDB	FooDB
Ocimum basilicum	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oenothera biennis	FooDB	FooDB
Olea europaea	FooDB	FooDB
Opuntia	FooDB	FooDB
Opuntia cochenillifera	FooDB	FooDB
Opuntia macrorhiza	FooDB	FooDB
Origanum majorana	FooDB	FooDB
Origanum onites	FooDB	FooDB
Origanum vulgare	FooDB	FooDB
Origanum X majoricum	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	FooDB
Ovis aries	FooDB	FooDB
Pachyrhizus erosus	FooDB	FooDB
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	FooDB
Passiflora edulis	FooDB	FooDB
Pastinaca sativa	FooDB	FooDB
Pediomelum esculentum	FooDB	FooDB
Perideridia oregana	FooDB	FooDB
Persea americana	FooDB	FooDB
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	FooDB
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phoenix dactylifera	FooDB	FooDB
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	FooDB
Physalis	FooDB	FooDB
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Pimenta dioica	FooDB	FooDB
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	FooDB
Pinus edulis	FooDB	FooDB
Piper nigrum L.	FooDB	FooDB
Pistacia vera	FooDB	FooDB
Pisum sativum	FooDB	FooDB
Pleurotus ostreatus	FooDB	FooDB
Polygonum alpinum	FooDB	FooDB
Portulaca oleracea	FooDB	FooDB
Pouteria sapota	FooDB	FooDB
Prunus armeniaca	FooDB	FooDB
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	FooDB
Prunus cerasus	FooDB	FooDB
Prunus domestica	FooDB	FooDB
Prunus dulcis	FooDB	FooDB
Prunus persica	FooDB	FooDB
Prunus persica var. nucipersica	FooDB	FooDB
Prunus persica var. persica	FooDB	FooDB
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Psidium cattleianum	FooDB	FooDB
Psidium guajava	FooDB	FooDB
Psophocarpus tetragonolobus	FooDB	FooDB
Punica granatum	FooDB	FooDB
Pyrus communis	FooDB	FooDB
Pyrus pyrifolia	FooDB	FooDB
Quercus	FooDB	FooDB
Raphanus sativus	FooDB	FooDB
Raphanus sativus var. longipinnatus	FooDB	FooDB
Raphanus sativus var. sativus	FooDB	FooDB
Rheum rhabarbarum	FooDB	FooDB
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	FooDB
Ribes rubrum	FooDB	FooDB
Ribes uva-crispa	FooDB	FooDB
Rosa	FooDB	FooDB
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	FooDB
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	FooDB
Rumex articus	FooDB	FooDB
Sagittaria latifolia	FooDB	FooDB
Salix pulchra	FooDB	FooDB
Salvia elegans	FooDB	FooDB
Salvia hispanica	FooDB	FooDB
Salvia officinalis	FooDB	FooDB
Salvia rosmarinus	FooDB	FooDB
Sambucus nigra	FooDB	FooDB
Sambucus nigra L.	FooDB	FooDB
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	FooDB
Scorzonera hispanica	FooDB	FooDB
Secale cereale	FooDB	FooDB
Sechium edule	FooDB	FooDB
Sesamum indicum	FooDB	FooDB
Sesbania bispinosa	FooDB	FooDB
Sinapis alba	FooDB	FooDB
Sisymbrium	FooDB	FooDB
Solanum lycopersicum	FooDB	FooDB
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	FooDB
Solanum melongena	FooDB	FooDB
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	FooDB
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	FooDB
Spinacia oleracea	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Syzygium aromaticum	FooDB	FooDB
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Tamarindus indica	FooDB	FooDB
Taraxacum officinale	FooDB	FooDB
Tetragonia tetragonioides	FooDB	FooDB
Thelesperma	FooDB	FooDB
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	FooDB
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Tragopogon porrifolius	FooDB	FooDB
Trigonella foenum-graecum	FooDB	FooDB
Triticum	FooDB	FooDB
Triticum aestivum	FooDB	FooDB
Triticum durum	FooDB	FooDB
Triticum spelta	FooDB	FooDB
Triticum turanicum	FooDB	FooDB
Typha angustifolia	FooDB	FooDB
Vaccinium	FooDB	FooDB
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	FooDB
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	FooDB
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	FooDB
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	FooDB
Valerianella locusta	FooDB	FooDB
Vanilla	FooDB	FooDB
Verbena officinalis	FooDB	FooDB
Viburnum edule	FooDB	FooDB
Vicia faba	FooDB	FooDB
Vigna aconitifolia	FooDB	FooDB
Vigna angularis	FooDB	FooDB
Vigna mungo	FooDB	FooDB
Vigna radiata	FooDB	FooDB
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	FooDB
Vigna unguiculata var. sesquipedalis	FooDB	FooDB
Vitis	FooDB	FooDB
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera L.	FooDB	FooDB
Xanthosoma sagittifolium	FooDB	FooDB
Zea mays L.	FooDB	FooDB
Zingiber officinale	FooDB	FooDB
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental 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

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

External Links

HMDB ID

HMDB0001372

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
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Showing NP-Card for Thiamine pyrophosphate (NP0001077)

MOL for NP0001077 (Thiamine pyrophosphate)

3D MOL for NP0001077 (Thiamine pyrophosphate)

3D SDF for NP0001077 (Thiamine pyrophosphate)

3D-SDF for NP0001077 (Thiamine pyrophosphate)

PDB for NP0001077 (Thiamine pyrophosphate)

3D PDB for NP0001077 (Thiamine pyrophosphate)

SMILES for NP0001077 (Thiamine pyrophosphate)

INCHI for NP0001077 (Thiamine pyrophosphate)

Structure for NP0001077 (Thiamine pyrophosphate)

3D Structure for NP0001077 (Thiamine pyrophosphate)