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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 19:52:36 UTC
Update Date2022-03-07 02:49:18 UTC
HMDB IDHMDB0003377
Secondary Accession Numbers
  • HMDB0006542
  • HMDB0006545
  • HMDB03377
  • HMDB06542
  • HMDB06545
Metabolite Identification
Common 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 ).
Structure
Data?1582752274
Synonyms
ValueSource
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
Chemical FormulaC26H40N7O19P3S
Average Molecular Weight879.618
Monoisotopic Molecular Weight879.131252359
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
Traditional Name4-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-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
CAS Registry Number6008-93-1
SMILES
CC(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
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.635Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-280.33930932474
DeepCCS[M+Na]+254.35830932474
AllCCS[M+H]+258.432859911
AllCCS[M+H-H2O]+258.932859911
AllCCS[M+NH4]+257.832859911
AllCCS[M+Na]+257.732859911
AllCCS[M-H]-258.932859911
AllCCS[M+Na-2H]-263.132859911
AllCCS[M+HCOO]-267.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Itaconyl-CoACC(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)=O6013.5Standard polar33892256
Itaconyl-CoACC(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)=O4649.1Standard non polar33892256
Itaconyl-CoACC(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)=O6827.1Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 10V, Positive-QTOFsplash10-000i-1912000130-a0d15736dbca763644c52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 20V, Positive-QTOFsplash10-000i-0914000000-f5921047fdb1e09c9f8a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 40V, Positive-QTOFsplash10-000i-1911000000-b2ee4c0270df2f4844002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 10V, Negative-QTOFsplash10-02e9-3911030350-cec965a2568415a08f9a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 20V, Negative-QTOFsplash10-001i-3911010000-e1c0353924ae80a756b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 40V, Negative-QTOFsplash10-0a7i-4900100000-0d29afcc209501d954372017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 10V, Negative-QTOFsplash10-004i-0000000090-d51d265d94e7b46860f32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 20V, Negative-QTOFsplash10-02vi-9300000570-d27d7bf6495cf3ec70a42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 40V, Negative-QTOFsplash10-0059-6202203900-88605810fe891129fe0d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 10V, Positive-QTOFsplash10-01q9-0000000090-9d97b0da9a4cfb7837a42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 20V, Positive-QTOFsplash10-01r6-0102200390-d8defc6031e05ec3b8c42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconyl-CoA 40V, Positive-QTOFsplash10-00di-0119000000-6c109556426b7495b96c2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023158
KNApSAcK IDNot Available
Chemspider ID388390
KEGG Compound IDC00531
BioCyc IDNot Available
BiGG ID35266
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439254
PDB IDNot Available
ChEBI ID15528
Food Biomarker OntologyNot Available
VMH IDITACCOA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceWillke T, Vorlop KD. Biotechnological production of itaconic acid. Appl Microbiol Biotechnol. 2001 Aug;56(3-4):289-95.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. WANG SF, ADLER J, LARDY HA: The pathway of itaconate metabolism by liver mitochondria. J Biol Chem. 1961 Jan;236:26-30. [PubMed:13783048 ]
  2. Willke T, Vorlop KD: Biotechnological production of itaconic acid. Appl Microbiol Biotechnol. 2001 Aug;56(3-4):289-95. [PubMed:11548996 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the ATP- or GTP-dependent ligation of succinate and CoA to form succinyl-CoA. The nature of the beta subunit determines the nucleotide specificity (By similarity).
Gene Name:
SUCLG1
Uniprot ID:
P53597
Molecular weight:
36249.505
General function:
Involved in catalytic activity
Specific function:
Catalyzes the GTP-dependent ligation of succinate and CoA to form succinyl-CoA (By similarity).
Gene Name:
SUCLG2
Uniprot ID:
Q96I99
Molecular weight:
47731.605
General function:
Involved in catalytic activity
Specific function:
Catalyzes the ATP-dependent ligation of succinate and CoA to form succinyl-CoA (By similarity).
Gene Name:
SUCLA2
Uniprot ID:
Q9P2R7
Molecular weight:
50316.88