Record Information
Version1.0
Created at2020-04-17 18:49:18 UTC
Updated at2020-11-18 16:38:58 UTC
CannabisDB IDCDB004908
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameThiamine pyrophosphate
DescriptionThiamine pyrophosphate, also known as thiamin diphosphoric acid or THPP, belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group. A 1,3-thiazolium cation that is the conjugate acid of thiamine(1+) diphosphate(1). Thiamine pyrophosphate is a very strong basic compound (based on its pKa). Thiamine pyrophosphate exists in all living species, ranging from bacteria to humans. Within humans, thiamine pyrophosphate participates in a number of enzymatic reactions. In particular, S-(2-methylbutanoyl)-dihydrolipoamide and thiamine pyrophosphate can be biosynthesized from lipoamide and 2-methyl-1-hydroxypropyl-THPP through the action of the enzymes 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial and 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial. In addition, ketoleucine and thiamine pyrophosphate can be converted into 3-methyl-1-hydroxybutyl-THPP; which is catalyzed by the enzyme 2-oxoisovalerate dehydrogenase. In humans, thiamine pyrophosphate is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. Thiamine pyrophosphate is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight425.31
Monoisotopic Molecular Weight425.045
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
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSThiamine pyrophosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-002b-9734000000-83738512818790cf1cc5Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0201900000-9ca110d3800e4ebfad43Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-0900000000-dad8835a4b26b1df86c4Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-2900000000-83b0eb52fe05e7097affSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0000900000-538ee08c2fc9a905eaadSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0309000000-b196fd5684e86907d04eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-0409000000-088cf88d5056ce245770Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9822000000-011b97ebb9fdcebffc93Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9200000000-2ecd5ee7eb283c5cd990Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-0001900000-59ea8d394aed62700202Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00b9-0614900000-08f09a377f03019f4457Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-0911000000-de2b56b98b01c6409b09Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-0900000000-7d75ca5105912446e47bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00di-2900000000-d632b8688f17a7a01de0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0000900000-538ee08c2fc9a905eaadSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0309000000-b196fd5684e86907d04eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0409000000-088cf88d5056ce245770Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9822000000-670f784e69ef56047333Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9200000000-2ecd5ee7eb283c5cd990Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0001900000-59ea8d394aed62700202Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0100900000-2d5d6c77c0c7e2d2d28aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aba-8146900000-e4efbc495cf0eb380395Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-4911100000-7e4a6eda3f297e8051b7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-08198f6dfeaa404b8b0fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9100200000-2d9e7e5d87267ce83dccSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9200000000-a470e5de9f124c159e0eSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Pyruvate dehydrogenase E1 component subunit beta, mitochondrialPDHB3p21.1-p14.2P11177 details
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialPDHA1Xp22.1P08559 details
Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrialPDHA24q22-q23P29803 details
2-oxoisovalerate dehydrogenase subunit beta, mitochondrialBCKDHB6q14.1P21953 details
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrialBCKDHA19q13.1-q13.2P12694 details
2-oxoglutarate dehydrogenase, mitochondrialOGDH7p14-p13Q02218 details
Thiamin pyrophosphokinase 1TPK17q34-q35Q9H3S4 details
Transketolase-like protein 1TKTL1Xq28P51854 details
TransketolaseTKT3p14.3P29401 details
Ectonucleoside triphosphate diphosphohydrolase 5ENTPD514q24O75356 details
Thiamine-triphosphataseTHTPA14q11.2Q9BU02 details
Transketolase-like protein 2TKTL24q32.2Q9H0I9 details
Acetolactate synthase-like proteinILVBL19p13.1A1L0T0 details
2-hydroxyacyl-CoA lyase 1HACL13p25.1Q9UJ83 details
Probable 2-oxoglutarate dehydrogenase E1 component DHKTD1, mitochondrialDHTKD110p14Q96HY7 details
2-oxoglutarate dehydrogenase-like, mitochondrialOGDHLQ9ULD0 details
Cancer-related nucleoside-triphosphataseNTPCR1q42.2Q9BSD7 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrialBCKDHA19q13.1-q13.2P12694 details
Transketolase-like protein 1TKTL1Xq28P51854 details
Thiamine-triphosphataseTHTPA14q11.2Q9BU02 details
Transketolase-like protein 2TKTL24q32.2Q9H0I9 details
Acetolactate synthase-like proteinILVBL19p13.1A1L0T0 details
2-hydroxyacyl-CoA lyase 1HACL13p25.1Q9UJ83 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001372
DrugBank IDDB01987
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022584
KNApSAcK IDC00019627
Chemspider ID1100
KEGG Compound IDC00068
BioCyc IDTHIAMINE-PYROPHOSPHATE
BiGG ID33732
Wikipedia LinkThiamine pyrophosphate
METLIN ID2832
PubChem Compound1132
PDB IDTDP
ChEBI ID9532
References
General ReferencesNot Available

Only showing the first 10 proteins. There are 23 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
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
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
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
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
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
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
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 23 proteins in total.