Record Information
Version1.0
Creation date2011-09-21 00:39:06 UTC
Update date2015-07-21 06:57:59 UTC
Primary IDFDB024054
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Carboxy-1-hydroxypropylthiamine diphosphate
Description3-Carboxy-1-hydroxypropyl-ThPP is an intermediate in Citrate cycle (TCA cycle). 3-Carboxy-1-hydroxypropyl-ThPP is the second to last step in the synthesis of Succinyl-CoA and is converted from 2-Oxoglutarate via the enzyme 2-oxoglutarate dehydrogenase E1 component (EC.1.2.4.2). It is then converted to S-Succinyldihydrolipoamide-E via the enzyme 2-oxoglutarate dehydrogenase E1 component (EC.1.2.4.2). [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
2-(3-Carboxy-1-hydroxypropyl)thiamine diphosphateChEBI
3-Carboxy-1-hydroxypropyl-THPPChEBI
Succinate semialdehyde-thiamin diphosphateKegg
2-(3-Carboxy-1-hydroxypropyl)thiamine diphosphoric acidGenerator
Succinic acid semialdehyde-thiamin diphosphoric acidGenerator
3-Carboxy-1-hydroxypropylthiamine diphosphoric acidGenerator
3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-2-(3-carboxy-1-hydroxypropyl)-5-(2-diphosphoethyl)-4-methyl-1,3-thiazol-3-iumHMDB
2-(3-Carboxy-1-hydroxypropyl)thiamine diateChEBI
2-(3-Carboxy-1-hydroxypropyl)thiamine diic acidGenerator
2-(3-carboxy-1-hydroxypropyl)thiamine diphosphatehmdb
3-[(4-amino-2-Methylpyrimidin-5-yl)methyl]-2-(3-carboxy-1-hydroxypropyl)-5-(2-dioethyl)-4-methyl-1,3-thiazol-3-iumHMDB
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-(3-carboxy-1-hydroxypropyl)-5-(2-diphosphoethyl)-4-methyl-1,3-thiazol-3-iumhmdb
3-Carboxy-1-hydroxypropyl-ThPPhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
logP-0.64ALOGPS
logP-7.3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)1.77ChemAxon
pKa (Strongest Basic)5.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area226.5 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity127.37 m³·mol⁻¹ChemAxon
Polarizability47.11 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H25N4O10P2S
IUPAC name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-(3-carboxy-1-hydroxypropyl)-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium
InChI IdentifierInChI=1S/C16H24N4O10P2S/c1-9-13(5-6-29-32(27,28)30-31(24,25)26)33-16(12(21)3-4-14(22)23)20(9)8-11-7-18-10(2)19-15(11)17/h7,12,21H,3-6,8H2,1-2H3,(H5-,17,18,19,22,23,24,25,26,27,28)/p+1
InChI KeyZWUKRGPVMMTMAF-UHFFFAOYSA-O
Isomeric SMILESCC1=C(CCOP(O)(=O)OP(O)(O)=O)SC(C(O)CCC(O)=O)=[N+]1CC1=C(N)N=C(C)N=C1
Average Molecular Weight527.403
Monoisotopic Molecular Weight527.076661754
Classification
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
  • 2,4,5-trisubstituted 1,3-thiazole
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Imidolactam
  • Phosphoric acid ester
  • Alkyl phosphate
  • Azole
  • Heteroaromatic compound
  • Thiazole
  • Amino acid or derivatives
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic alcohol
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS3-Carboxy-1-hydroxypropylthiamine diphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ki2-8853930000-2d20db61c35c735c6726Spectrum
Predicted GC-MS3-Carboxy-1-hydroxypropylthiamine diphosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-8080197000-6f52c57ca3a187968f4bSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-055e-0246950000-bac6074dcea868b654a7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-4319200000-b9cec10cb173f2d20023Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-1962000000-76c3988b185ec2f13f69Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05di-0300960000-6d763b4c58b5627dbbe3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0205910000-63d4b7f4c17e449a6f57Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2937100000-ab1d8c9956ba46638067Spectrum
NMRNot Available
ChemSpider ID389531
ChEMBL IDNot Available
KEGG Compound IDC05381
Pubchem Compound ID440649
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06744
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
2-oxoglutarate dehydrogenase, mitochondrialOGDHQ02218
2-oxoglutarate dehydrogenase-like, mitochondrialOGDHLQ9ULD0
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference