Itaconic acid (PAMDB000440)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000440
Identification
Name: Itaconic acid
Description:Itaconic acid is an intermediate in the C5-Branched dibasic acid metabolism, a substrate for the enzyme Succinate-CoA ligase (ADP-forming) (EC:6.2.1.5)(Kegg)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-Hydroxy-3-Naphthoyl-2-Naphthylamine
  • 2-Methylenesuccinate
  • 2-Methylenesuccinic acid
  • 2-Methylsuccinate
  • 2-Methylsuccinic acid
  • 2-Propene-1,2-dicarboxylate
  • 2-Propene-1,2-dicarboxylic acid
  • Itaconate
  • Itaconic acid
  • Methylenebutanedioate
  • Methylenebutanedioic acid
  • Methylenesuccinate
  • Methylenesuccinic acid
  • Propylenedicarboxylate
  • Propylenedicarboxylic acid
Chemical Formula: C5H6O4
Average Molecular Weight: 130.0987
Monoisotopic Molecular Weight: 130.02660868
InChI Key: LVHBHZANLOWSRM-UHFFFAOYSA-N
InChI:InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
CAS number: 97-65-4
IUPAC Name:2-methylidenebutanedioic acid
Traditional IUPAC Name: itaconic acid
SMILES:OC(=O)CC(=C)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Branched fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 175 °C
Experimental Properties:
PropertyValueSource
Water Solubility:76.8 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility63.0 mg/mLALOGPS
logP0ALOGPS
logP0.053ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.91 m3·mol-1ChemAxon
Polarizability11.06 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + Itaconic acid + Coenzyme A > Adenosine diphosphate + Phosphate + Itaconyl-CoA + ADP
Pathways:
  • C5-Branched dibasic acid metabolism pae00660
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-067j-4970000000-62c083c1889c0389bdc7View in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03y1-9400000000-8522d5eb5288a63433b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-00kr-9000000000-8287612bcdd337cb94ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-02a9-9200000000-d17287465b81dab7939cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-4900000000-8433e22f39cee33233c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-5879e62dedd6aab4b1caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-464f41418a542f68cdb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-96ec7055deb2e0402943View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-f4499898bdcf9c9eb9c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9100000000-dac578cf4d95b2206d4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-4900000000-8dbdce71f36577627d67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02g9-9300000000-72767f1807dfa80e809cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-e26167424a1c652a920dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-5900000000-95e66a8f3b6c0bc3cec6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-9500000000-c8ab0cb1983e8213e622View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-9000000000-f54d12caffc54c552d2dView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Karadag E, Saraydin D, Cetinkaya S, Guven O: In vitro swelling studies and preliminary biocompatibility evaluation of acrylamide-based hydrogels. Biomaterials. 1996 Jan;17(1):67-70. Pubmed: 8962950
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID30838
HMDB IDHMDB02092
Pubchem Compound ID811
Kegg IDC00490
ChemSpider ID789
WikipediaItaconic acid
BioCyc IDITACONATE
EcoCyc IDITACONATE