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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:29 UTC
HMDB IDHMDB0001372
Secondary Accession Numbers
  • HMDB0062636
  • HMDB01372
  • HMDB62636
Metabolite Identification
Common NameThiamine pyrophosphate
DescriptionThiamine 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
Data?1600368042
Synonyms
ValueSource
Thiamin diphosphateChEBI
Thiamin pyrophosphateChEBI
Thiamine diphosphateChEBI
THPPChEBI
TPPChEBI
Thiamin diphosphoric acidGenerator
Thiamin pyrophosphoric acidGenerator
Thiamine diphosphoric acidGenerator
Thiamine pyrophosphoric acidGenerator
Thaimine pyrophosphateHMDB
Thiamin-ppiHMDB
Thiamine-ppiHMDB
Thiamine-pyrophosphateHMDB
CocarboxylaseHMDB
BerolaseHMDB
Pyrophosphate, thiamineHMDB
Chemical FormulaC12H19N4O7P2S
Average Molecular Weight425.314
Monoisotopic Molecular Weight425.044967696
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium
Traditional Namethiamin pyrophosphate
CAS Registry Number136-09-4
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 KeyAYEKOFBPNLCAJY-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentThiamine phosphates
Alternative Parents
Substituents
  • Thiamine-phosphate
  • Organic pyrophosphate
  • 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP-1.2ALOGPS
logP-5.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)5.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area168.97 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.15 m³·mol⁻¹ChemAxon
Polarizability36.96 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+192.26931661259
DarkChem[M+H]+192.26931661259
DarkChem[M-H]-185.8831661259
DarkChem[M-H]-185.8831661259
AllCCS[M+H]+189.35532859911
AllCCS[M-H]-184.18432859911
DeepCCS[M+H]+156.08930932474
DeepCCS[M-H]-153.7330932474
DeepCCS[M-2H]-188.09330932474
DeepCCS[M+Na]+163.60330932474
AllCCS[M+H]+189.432859911
AllCCS[M+H-H2O]+187.132859911
AllCCS[M+NH4]+191.432859911
AllCCS[M+Na]+192.032859911
AllCCS[M-H]-184.232859911
AllCCS[M+Na-2H]-184.732859911
AllCCS[M+HCOO]-185.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Thiamine pyrophosphateCC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N4652.2Standard polar33892256
Thiamine pyrophosphateCC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N2938.3Standard non polar33892256
Thiamine pyrophosphateCC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N3548.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Thiamine pyrophosphate,1TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N)=N13503.0Semi standard non polar33892256
Thiamine pyrophosphate,1TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N)=N13175.9Standard non polar33892256
Thiamine pyrophosphate,1TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N)=N15436.9Standard polar33892256
Thiamine pyrophosphate,1TMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N13473.5Semi standard non polar33892256
Thiamine pyrophosphate,1TMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N13183.1Standard non polar33892256
Thiamine pyrophosphate,1TMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N15440.4Standard polar33892256
Thiamine pyrophosphate,1TMS,isomer #3CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N13545.2Semi standard non polar33892256
Thiamine pyrophosphate,1TMS,isomer #3CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N13132.4Standard non polar33892256
Thiamine pyrophosphate,1TMS,isomer #3CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N15580.9Standard polar33892256
Thiamine pyrophosphate,2TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N13448.3Semi standard non polar33892256
Thiamine pyrophosphate,2TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N13261.7Standard non polar33892256
Thiamine pyrophosphate,2TMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N14938.9Standard polar33892256
Thiamine pyrophosphate,2TMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N13491.8Semi standard non polar33892256
Thiamine pyrophosphate,2TMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N13221.0Standard non polar33892256
Thiamine pyrophosphate,2TMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N14922.4Standard polar33892256
Thiamine pyrophosphate,2TMS,isomer #3CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N13450.9Semi standard non polar33892256
Thiamine pyrophosphate,2TMS,isomer #3CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N13248.6Standard non polar33892256
Thiamine pyrophosphate,2TMS,isomer #3CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)=C2C)C(N)=N15009.9Standard polar33892256
Thiamine pyrophosphate,2TMS,isomer #4CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N13475.6Semi standard non polar33892256
Thiamine pyrophosphate,2TMS,isomer #4CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N13215.5Standard non polar33892256
Thiamine pyrophosphate,2TMS,isomer #4CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N[Si](C)(C)C)=N14982.7Standard polar33892256
Thiamine pyrophosphate,2TMS,isomer #5CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N13481.8Semi standard non polar33892256
Thiamine pyrophosphate,2TMS,isomer #5CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N13273.0Standard non polar33892256
Thiamine pyrophosphate,2TMS,isomer #5CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N([Si](C)(C)C)[Si](C)(C)C)=N15171.3Standard polar33892256
Thiamine pyrophosphate,3TMS,isomer #1CC1=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)=N13454.0Semi standard non polar33892256
Thiamine pyrophosphate,3TMS,isomer #1CC1=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)=N13266.2Standard non polar33892256
Thiamine pyrophosphate,3TMS,isomer #1CC1=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)=N14610.5Standard polar33892256
Thiamine pyrophosphate,3TMS,isomer #2CC1=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)=N13485.2Semi standard non polar33892256
Thiamine pyrophosphate,3TMS,isomer #2CC1=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)=N13272.1Standard non polar33892256
Thiamine pyrophosphate,3TMS,isomer #2CC1=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)=N14506.9Standard polar33892256
Thiamine pyrophosphate,3TMS,isomer #3CC1=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)=N13477.0Semi standard non polar33892256
Thiamine pyrophosphate,3TMS,isomer #3CC1=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)=N13326.5Standard non polar33892256
Thiamine pyrophosphate,3TMS,isomer #3CC1=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)=N14610.1Standard polar33892256
Thiamine pyrophosphate,3TMS,isomer #4CC1=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)=N13482.1Semi standard non polar33892256
Thiamine pyrophosphate,3TMS,isomer #4CC1=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)=N13262.6Standard non polar33892256
Thiamine pyrophosphate,3TMS,isomer #4CC1=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)=N14529.7Standard polar33892256
Thiamine pyrophosphate,3TMS,isomer #5CC1=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)=N13463.1Semi standard non polar33892256
Thiamine pyrophosphate,3TMS,isomer #5CC1=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)=N13312.6Standard non polar33892256
Thiamine pyrophosphate,3TMS,isomer #5CC1=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)=N14683.2Standard polar33892256
Thiamine pyrophosphate,4TMS,isomer #1CC1=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)=N13513.2Semi standard non polar33892256
Thiamine pyrophosphate,4TMS,isomer #1CC1=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)=N13285.2Standard non polar33892256
Thiamine pyrophosphate,4TMS,isomer #1CC1=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)=N14088.4Standard polar33892256
Thiamine pyrophosphate,4TMS,isomer #2CC1=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)=N13478.8Semi standard non polar33892256
Thiamine pyrophosphate,4TMS,isomer #2CC1=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)=N13332.0Standard non polar33892256
Thiamine pyrophosphate,4TMS,isomer #2CC1=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)=N14223.5Standard polar33892256
Thiamine pyrophosphate,4TMS,isomer #3CC1=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)=N13479.3Semi standard non polar33892256
Thiamine pyrophosphate,4TMS,isomer #3CC1=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)=N13324.3Standard non polar33892256
Thiamine pyrophosphate,4TMS,isomer #3CC1=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)=N14224.2Standard polar33892256
Thiamine pyrophosphate,5TMS,isomer #1CC1=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)=N13504.4Semi standard non polar33892256
Thiamine pyrophosphate,5TMS,isomer #1CC1=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)=N13319.7Standard non polar33892256
Thiamine pyrophosphate,5TMS,isomer #1CC1=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)=N13837.3Standard polar33892256
Thiamine pyrophosphate,1TBDMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N)=N13736.9Semi standard non polar33892256
Thiamine pyrophosphate,1TBDMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N)=N13366.3Standard non polar33892256
Thiamine pyrophosphate,1TBDMS,isomer #1CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N)=N15511.0Standard polar33892256
Thiamine pyrophosphate,1TBDMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N13717.0Semi standard non polar33892256
Thiamine pyrophosphate,1TBDMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N13374.5Standard non polar33892256
Thiamine pyrophosphate,1TBDMS,isomer #2CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N15512.0Standard polar33892256
Thiamine pyrophosphate,1TBDMS,isomer #3CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N13753.6Semi standard non polar33892256
Thiamine pyrophosphate,1TBDMS,isomer #3CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N13320.7Standard non polar33892256
Thiamine pyrophosphate,1TBDMS,isomer #3CC1=NC=C(C[N+]2=CSC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N15517.7Standard polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #1CC1=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)=N13885.9Semi standard non polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #1CC1=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)=N13589.6Standard non polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #1CC1=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)=N15068.7Standard polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #2CC1=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)=N13917.6Semi standard non polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #2CC1=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)=N13560.9Standard non polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #2CC1=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)=N15029.9Standard polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #3CC1=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)=N13892.3Semi standard non polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #3CC1=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)=N13570.3Standard non polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #3CC1=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)=N15136.8Standard polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #4CC1=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)=N13898.2Semi standard non polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #4CC1=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)=N13564.3Standard non polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #4CC1=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)=N15084.8Standard polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #5CC1=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)=N13907.4Semi standard non polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #5CC1=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)=N13623.4Standard non polar33892256
Thiamine pyrophosphate,2TBDMS,isomer #5CC1=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)=N15165.0Standard polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #1CC1=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)=N14028.8Semi standard non polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #1CC1=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)=N13691.5Standard non polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #1CC1=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)=N14751.5Standard polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #2CC1=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)=N14056.0Semi standard non polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #2CC1=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)=N13734.6Standard non polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #2CC1=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)=N14680.4Standard polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #3CC1=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)=N14076.7Semi standard non polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #3CC1=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)=N13793.5Standard non polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #3CC1=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)=N14749.9Standard polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #4CC1=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)=N14059.4Semi standard non polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #4CC1=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)=N13717.1Standard non polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #4CC1=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)=N14711.6Standard polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #5CC1=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)=N14056.5Semi standard non polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #5CC1=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)=N13792.1Standard non polar33892256
Thiamine pyrophosphate,3TBDMS,isomer #5CC1=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)=N14817.1Standard polar33892256
Thiamine pyrophosphate,4TBDMS,isomer #1CC1=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)=N14233.1Semi standard non polar33892256
Thiamine pyrophosphate,4TBDMS,isomer #1CC1=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)=N13834.5Standard non polar33892256
Thiamine pyrophosphate,4TBDMS,isomer #1CC1=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)=N14337.3Standard polar33892256
Thiamine pyrophosphate,4TBDMS,isomer #2CC1=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)=N14224.2Semi standard non polar33892256
Thiamine pyrophosphate,4TBDMS,isomer #2CC1=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)=N13900.4Standard non polar33892256
Thiamine pyrophosphate,4TBDMS,isomer #2CC1=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)=N14409.0Standard polar33892256
Thiamine pyrophosphate,4TBDMS,isomer #3CC1=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)=N14225.4Semi standard non polar33892256
Thiamine pyrophosphate,4TBDMS,isomer #3CC1=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)=N13879.3Standard non polar33892256
Thiamine pyrophosphate,4TBDMS,isomer #3CC1=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)=N14428.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Thiamine pyrophosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-9734000000-83738512818790cf1cc52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Thiamine pyrophosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-004i-0201900000-9ca110d3800e4ebfad432012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00di-0900000000-dad8835a4b26b1df86c42012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00di-2900000000-83b0eb52fe05e7097aff2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-00di-0000900000-538ee08c2fc9a905eaad2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0udi-0309000000-b196fd5684e86907d04e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0udi-0409000000-088cf88d5056ce2457702012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-004i-9822000000-011b97ebb9fdcebffc932012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-004i-9200000000-2ecd5ee7eb283c5cd9902012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-004i-0001900000-59ea8d394aed627002022012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-00b9-0614900000-08f09a377f03019f44572012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-00di-0911000000-de2b56b98b01c6409b092012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-00di-0900000000-7d75ca5105912446e47b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-00di-2900000000-d632b8688f17a7a01de02012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , negative-QTOFsplash10-00di-0000900000-538ee08c2fc9a905eaad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , negative-QTOFsplash10-0udi-0309000000-b196fd5684e86907d04e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , negative-QTOFsplash10-0udi-0409000000-088cf88d5056ce2457702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , negative-QTOFsplash10-004i-9822000000-670f784e69ef560473332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , negative-QTOFsplash10-004i-9200000000-2ecd5ee7eb283c5cd9902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Thiamine pyrophosphate LC-ESI-QQ , positive-QTOFsplash10-004i-0001900000-59ea8d394aed627002022017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine pyrophosphate 10V, Positive-QTOFsplash10-004i-0100900000-2d5d6c77c0c7e2d2d28a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine pyrophosphate 20V, Positive-QTOFsplash10-0aba-8146900000-e4efbc495cf0eb3803952016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine pyrophosphate 40V, Positive-QTOFsplash10-0a4j-4911100000-7e4a6eda3f297e8051b72016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine pyrophosphate 10V, Negative-QTOFsplash10-00di-0000900000-08198f6dfeaa404b8b0f2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine pyrophosphate 20V, Negative-QTOFsplash10-001i-9100200000-2d9e7e5d87267ce83dcc2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Thiamine pyrophosphate 40V, Negative-QTOFsplash10-004j-9200000000-a470e5de9f124c159e0e2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Locations
  • Brain
  • Erythrocyte
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0032 +/- 0.0022 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.034 (0-0.066) uMAdult (>18 years old)Not Specified
Cerebrocortical Degeneration
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0025 +/- 0.0017 uMAdult (>18 years old)BothAlzheimer's disease details
Associated Disorders and Diseases
Disease References
Cerebrocortical degeneration
  1. 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
  1. 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
DrugBank IDDB01987
Phenol Explorer Compound IDNot Available
FooDB IDFDB022584
KNApSAcK IDC00019627
Chemspider ID1100
KEGG Compound IDC00068
BioCyc IDTHIAMINE-PYROPHOSPHATE
BiGG ID33732
Wikipedia LinkThiamine pyrophosphate
METLIN ID2832
PubChem Compound1132
PDB IDTDP
ChEBI ID9532
Food Biomarker OntologyNot Available
VMH IDTHMPP
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceZabrodskaya, 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
  1. 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 ]
  2. Singleton CK, Martin PR: Molecular mechanisms of thiamine utilization. Curr Mol Med. 2001 May;1(2):197-207. [PubMed:11899071 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Warnock LG: The measurement of erythrocyte thiamin pyrophosphate by high-performance liquid chromatography. Anal Biochem. 1982 Nov 1;126(2):394-7. [PubMed:7158773 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. Duffy P, Morris H, Neilson G: Thiamin status of a Melanesian population. Am J Clin Nutr. 1981 Aug;34(8):1584-92. [PubMed:7270482 ]
  12. Kjosen B, Seim SH: The transketolase assay of thiamine in some diseases. Am J Clin Nutr. 1977 Oct;30(10):1591-6. [PubMed:910736 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]
  21. 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.

Enzymes

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 dioxidedetails
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphatedetails
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 dioxidedetails
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphatedetails
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 dioxidedetails
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphatedetails
General function:
Involved in catalytic activity
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHB
Uniprot ID:
P21953
Molecular weight:
43122.065
Reactions
alpha-Ketoisovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxidedetails
2-Methyl-1-hydroxypropyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + Thiamine pyrophosphatedetails
Ketoleucine + Thiamine pyrophosphate → 3-Methyl-1-hydroxybutyl-ThPP + Carbon dioxidedetails
3-Methyl-1-hydroxybutyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(3-methylbutanoyl)dihydrolipoyllysine + Thiamine pyrophosphatedetails
3-Methyl-2-oxovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxybutyl-ThPP + Carbon dioxidedetails
2-Methyl-1-hydroxybutyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylbutanoyl)dihydrolipoyllysine + Thiamine pyrophosphatedetails
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHA
Uniprot ID:
P12694
Molecular weight:
50470.58
Reactions
alpha-Ketoisovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxidedetails
2-Methyl-1-hydroxypropyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + Thiamine pyrophosphatedetails
Ketoleucine + Thiamine pyrophosphate → 3-Methyl-1-hydroxybutyl-ThPP + Carbon dioxidedetails
3-Methyl-1-hydroxybutyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(3-methylbutanoyl)dihydrolipoyllysine + Thiamine pyrophosphatedetails
3-Methyl-2-oxovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxybutyl-ThPP + Carbon dioxidedetails
2-Methyl-1-hydroxybutyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylbutanoyl)dihydrolipoyllysine + Thiamine pyrophosphatedetails
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 dioxidedetails
3-Carboxy-1-hydroxypropylthiamine diphosphate + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine + Thiamine pyrophosphatedetails
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 pyrophosphatedetails
Adenosine triphosphate + Thiamine pyrophosphate → ADP + Thiamine triphosphatedetails
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
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
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.