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Record Information
Version2.0
Creation Date2012-08-09 09:25:32 -0600
Update Date2015-06-03 17:21:48 -0600
Secondary Accession Numbers
  • ECMDB21572
Identification
Name:Succinate-semialdehyde-thiamine PPi
DescriptionSuccinate-semialdehyde-thiamine pyrophosphate is a thiamine derivative. The first intermediate (SHCHC) in the menaquinone biosynthetic pathway, requires two reactions. The first is the decarboxylation of alpha-ketoglutarate by an alpha-ketoglutarate decarboxylase, which results in the formation of succinic semialdehyde-thiamine PPi (TPP) anion, and the second is the addition of the succinic semialdehyde-TPP anion to isochorismate, which is carried out by the enzyme SHCHC synthase. Both enzymatic activities are encoded by the menD gene [PMID: 1459959]
Structure
Thumb
Synonyms:
  • Succinic acid-semialdehyde-thiamine ppi
  • Succinic semialdehyde-thiamine pyrophosphate
  • Succinic semialdehyde-thiamine pyrophosphoric acid
Chemical Formula:C16H22N4O10P2S
Weight:Average: 524.379
Monoisotopic: 524.053186658
InChI Key:JUWXHVVKSHTJQQ-UHFFFAOYSA-L
InChI:InChI=1S/C16H24N4O10P2S/c1-10-13(33-9-20(10)8-12-7-18-11(2)19-16(12)17)5-6-28-31(24,25)30-32(26,27)29-15(23)4-3-14(21)22/h7,9,15,23H,3-6,8H2,1-2H3,(H4-,17,18,19,21,22,24,25,26,27)/p-2
CAS number:Not Available
IUPAC Name:5-[2-({[(3-carboxylato-1-hydroxypropyl phosphonato)oxy]phosphinato}oxy)ethyl]-3-[(6-imino-2-methyl-1,6-dihydropyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium
Traditional IUPAC Name:5-(2-{[(3-carboxylato-1-hydroxypropyl phosphonato)oxyphosphinato]oxy}ethyl)-3-[(4-imino-2-methyl-3H-pyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium
SMILES:CC1=C(CCOP([O-])(=O)OP([O-])(=O)OC(O)CCC([O-])=O)SC=[N+]1CC1=CN=C(C)NC1=N
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
  • Imidolactam
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Hydropyrimidine
  • Heteroaromatic compound
  • Thiazole
  • Azole
  • Carboxylic acid salt
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP-0.99ALOGPS
logP-8.3ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)7.04ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area220.43 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity133.68 m³·mol⁻¹ChemAxon
Polarizability45.63 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1200090000-e95b766bd380abe1141eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-5230190000-15d9e68c2638ed78ec56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9400000000-ae83ce4306720ef4a8ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1000090000-ba36290277a4c6eb8ebaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-6410490000-235480720ac022326161View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fu2-6790000000-a21b893baefdc3a684c2View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID45479398
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in thiamine pyrophosphate binding
Specific function:
Catalyzes the thiamine diphosphate-dependent decarboxylation of 2-oxoglutarate and the subsequent addition of the resulting succinic semialdehyde-thiamine pyrophosphate anion to isochorismate to yield 2-succinyl-5-enolpyruvyl-6-hydroxy-3- cyclohexene-1-carboxylate (SEPHCHC)
Gene Name:
menD
Uniprot ID:
P17109
Molecular weight:
61367
Reactions
Isochorismate + 2-oxoglutarate = 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO(2).