thiamine(1+) diphosphate(1-) (YMDB01093)

Identification
YMDB IDYMDB01093
Namethiamine(1+) diphosphate(1-)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionThiamine(1+) Diphosphate(1-), also known as thiamine pyrophosphate or thiamine diphosphoric acid, 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. Thiamine(1+) Diphosphate(1-) is a very strong basic compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • cocarboxylase
  • Thaimine pyrophosphate
  • thiamin diphosphate
  • thiamin pyrophosphate
  • thiamin-PPi
  • thiamine diphosphate
  • Thiamine pyrophosphate
  • Thiamine pyrophosphic acid
  • thiamine-PPi
  • thiamine-pyrophosphate
  • ThPP
  • TPP
  • tpp, thpp
  • THIAMIN diphosphoric acid
  • Thiamin pyrophosphoric acid
  • THIAMINE diphosphoric acid
  • Thiamine pyrophosphoric acid
  • Thiamine(1+) diphosphoric acid(1-)
  • Berolase
  • Pyrophosphate, thiamine
CAS numberNot Available
WeightAverage: 424.306
Monoisotopic: 424.037142664
InChI KeyAYEKOFBPNLCAJY-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(hydrogen phosphonatooxy)(hydroxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium
Traditional IUPAC Namethiamin diphosphate
Chemical FormulaC12H18N4O7P2S
SMILESCC1=C(CCOP(O)(=O)OP(O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N
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
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Imidolactam
  • Azole
  • Heteroaromatic compound
  • Thiazole
  • Azacycle
  • Amine
  • Primary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP-1.2ALOGPS
logP-5.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)5.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area171.8 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.02 m³·mol⁻¹ChemAxon
Polarizability35.85 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • extracellular
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Citric Acid CyclePW000952 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid Cycle 1434561204PW000970 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA CyclePW002377 ThumbThumb?image type=greyscaleThumb?image type=simple
Vitamin B1/Thiamine metabolismPW002486 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Pyruvate metabolismec00620 Map00620
SMPDB ReactionsNot Available
KEGG Reactions
water + thiamine(1+) diphosphate(1-) Thiamine + phosphate + hydron
Adenosine triphosphate + Thiamine → Adenosine monophosphate + thiamine(1+) diphosphate(1-) + hydron
Adenosine triphosphate + thiamine(1+) diphosphate(1-) → Thiamine triphosphate + ADP
Adenosine triphosphate + Thiamine monophosphate ↔ thiamine(1+) diphosphate(1-) + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-8936000000-119f14d7b717fad84f6bJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-03di-2590000000-3b56b15f83f1eb31bbd6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0100900000-77873d5d6dd317537d7dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aba-7147900000-0079e51a57e998b4c558JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-4920000000-6090fb0a45c94831fa87JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-e1117ba0cbb3b3bfd1a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9200200000-4c89cd71f5a2d5ca1cd5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9100000000-c1192b7bec0b5f39eacfJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID45931
HMDB IDHMDB0062636
Pubchem Compound ID5431
Kegg IDNot Available
ChemSpider ID5238
FOODB IDNot Available
Wikipedia IDThiamine pyrophosphate
BioCyc IDTHIAMINE-PYROPHOSPHATE