You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.

Record Information
Version1.0
Created at2006-05-22 14:17:36 UTC
Updated at2020-09-11 01:14:49 UTC
NP-MRD IDNP0000015
Secondary Accession NumbersNone
Natural Product Identification
Common NameItaconic acid
DescriptionItaconic acid, also known as itaconate, belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain. Itaconic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
2-Methylenesuccinic acidChEBI
2-Propene-1,2-dicarboxylic acidChEBI
Methylenebutanedioic acidChEBI
Methylenesuccinic acidChEBI
Propylenedicarboxylic acidChEBI
2-MethylenesuccinateGenerator
2-Propene-1,2-dicarboxylateGenerator
MethylenebutanedioateGenerator
MethylenesuccinateGenerator
PropylenedicarboxylateGenerator
ItaconateGenerator
2-Hydroxy-3-naphthoyl-2-naphthylamineHMDB
Itaconic acid, copper saltHMDB
Itaconic acid, disodium saltHMDB
Itaconic acid, calcium saltHMDB
Itaconic acid, sodium saltHMDB
Chemical FormulaC5H6O4
Average Molecular Weight130.0987
Monoisotopic Molecular Weight130.02660868
IUPAC Name2-methylidenebutanedioic acid
Traditional Nameitaconic acid
CAS Registry Number97-65-4
SMILES
OC(=O)CC(=C)C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
InChI KeyLVHBHZANLOWSRM-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR13C NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR13C NMR SpectrumJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesEubacteria; Fungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentBranched fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point175 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility76.8 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility63 g/LALOGPS
logP0ALOGPS
logP0.053ChemAxon
logS-0.31ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.91 m³·mol⁻¹ChemAxon
Polarizability11.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0002092
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012645
KNApSAcK IDC00033964
Chemspider ID789
KEGG Compound IDC00490
BioCyc IDITACONATE
BiGG ID35130
Wikipedia LinkItaconic_acid
METLIN ID6483
PubChem Compound811
PDB IDNot Available
ChEBI ID30838
References
General References
  1. 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 ]