Record Information
Version1.0
Creation date2011-09-21 00:25:31 UTC
Update date2019-11-26 03:21:07 UTC
Primary IDFDB023158
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameItaconyl-CoA
DescriptionItaconyl-CoA is an intermediate metabolite in the degradation pathway of itaconic acid, an unsaturated dicarbonic organic acid. Citramalyl coenzyme A (CoA) is found to be the intermediate in the conversion of itaconyl-Co-A to acetyl-CoA and pyruvate, catalyzed by methylglutaconase. Methylglutaconase catalyzes the interconversion of itaconyl-, mesaconyl-, and citramalyl-CoA. In liver mitochondria, methylglutaconase converts itaconate to pyruvate and acetyl coenzyme A. In this metabolic process, itaconate is first activated to itaconyl-CoA by a succinate activating enzyme, and a CoA derivative is cleaved to acetyl-CoA and pyruvate. (PMID: 13783048, 11548996) [HMDB]. Itaconyl-CoA is found in many foods, some of which are red algae, barley, garden rhubarb, and chestnut.
CAS Number6008-93-1
Structure
Thumb
Synonyms
SynonymSource
Itaconoyl CoAHMDB
Itaconoyl coenzyme AHMDB
S-(1-Hydrogen methylenesuccinate) CoAHMDB
S-(1-Hydrogen methylenesuccinate) coenzyme AHMDB
S-3-Methylenesuccinate CoAHMDB
S-3-Methylenesuccinate coenzyme AHMDB
S-Itaconate CoAHMDB
S-Itaconate coenzyme AHMDB
S-(1-hydrogen methylenesuccinate) CoAhmdb
S-(1-hydrogen methylenesuccinate) Coenzyme Ahmdb
S-3-methylenesuccinate CoAhmdb
S-3-methylenesuccinate Coenzyme Ahmdb
S-itaconate CoAhmdb
S-itaconate Coenzyme Ahmdb
Predicted Properties
PropertyValueSource
Water Solubility3.71 g/LALOGPS
logP-0.44ALOGPS
logP-6.7ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area400.93 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity187.48 m³·mol⁻¹ChemAxon
Polarizability75.93 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H40N7O19P3S
IUPAC name4-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-methylidene-4-oxobutanoic acid
InChI IdentifierInChI=1S/C26H40N7O19P3S/c1-13(25(39)40)8-16(35)56-7-6-28-15(34)4-5-29-23(38)20(37)26(2,3)10-49-55(46,47)52-54(44,45)48-9-14-19(51-53(41,42)43)18(36)24(50-14)33-12-32-17-21(27)30-11-31-22(17)33/h11-12,14,18-20,24,36-37H,1,4-10H2,2-3H3,(H,28,34)(H,29,38)(H,39,40)(H,44,45)(H,46,47)(H2,27,30,31)(H2,41,42,43)/t14-,18-,19-,20?,24-/m1/s1
InChI KeyNFVGYLGSSJPRKW-XBTRWLRFSA-N
Isomeric SMILESCC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)C(O)C(=O)NCCC(=O)NCCSC(=O)CC(=C)C(O)=O
Average Molecular Weight879.618
Monoisotopic Molecular Weight879.131252359
Classification
Description Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000130-a0d15736dbca763644c5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0914000000-f5921047fdb1e09c9f8aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1911000000-b2ee4c0270df2f484400Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02e9-3911030350-cec965a2568415a08f9aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3911010000-e1c0353924ae80a756b3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a7i-4900100000-0d29afcc209501d95437Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000000090-d51d265d94e7b46860f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02vi-9300000570-d27d7bf6495cf3ec70a4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-6202203900-88605810fe891129fe0dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0000000090-9d97b0da9a4cfb7837a4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01r6-0102200390-d8defc6031e05ec3b8c4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0119000000-6c109556426b7495b96cSpectrum
NMRNot Available
ChemSpider ID388390
ChEMBL IDNot Available
KEGG Compound IDC00531
Pubchem Compound ID439254
Pubchem Substance IDNot Available
ChEBI ID15528
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03377
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35266
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference