Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:36 UTC
Update Date2021-09-07 16:45:32 UTC
HMDB IDHMDB0002092
Secondary Accession Numbers
  • HMDB02092
Metabolite Identification
Common NameItaconic acid
DescriptionItaconic acid is a dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group. It has a role as a fungal metabolite and a human metabolite. It is a dicarboxylic acid and an olefinic compound. It derives from a succinic acid. It is a conjugate acid of an itaconate(2-). This dicarboxylic acid is a white solid that is soluble in water, ethanol, and acetone. Historically, itaconic acid was obtained by the distillation of citric acid, but currently it is produced by fermentation. The name itaconic acid was devised as an anagram of aconitic acid, another derivative of citric acid. Itaconic 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. Since the 1960s, it is produced industrially by the fermentation of carbohydrates such as glucose or molasses using fungi such as Aspergillus itaconicus or Aspergillus terreus. For A. terreus the itaconate pathway is mostly elucidated. The generally accepted route for itaconate is via glycolysis, tricarboxylic acid cycle, and a decarboxylation of cis-aconitate to itaconate via cis-aconitate-decarboxylase. The smut fungus Ustilago maydis uses an alternative route. Cis-aconitate is converted to the thermodynamically favoured trans-aconitate via aconitate-Δ-isomerase (Adi1). trans-Aconitate is further decarboxylated to itaconate by trans-aconitate-decarboxylase (Tad1). Itaconic acid is also produced in cells of macrophage lineage. It was shown that itaconate is a covalent inhibitor of the enzyme isocitrate lyase in vitro. As such, itaconate may possess antibacterial activities against bacteria expressing isocitrate lyase (such as Salmonella enterica and Mycobacterium tuberculosis). It is also sythesized in the laboratory, where dry distillation of citric acid affords itaconic anhydride, which undergoes hydrolysis to itaconic acid.
Structure
Data?1582752229
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
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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point175 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility76.8 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available119.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00002147
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.59431661259
DarkChem[M-H]-120.73831661259
DeepCCS[M+H]+123.92130932474
DeepCCS[M-H]-120.78730932474
DeepCCS[M-2H]-157.6530932474
DeepCCS[M+Na]+132.56130932474
AllCCS[M+H]+130.732859911
AllCCS[M+H-H2O]+126.532859911
AllCCS[M+NH4]+134.632859911
AllCCS[M+Na]+135.732859911
AllCCS[M-H]-123.532859911
AllCCS[M+Na-2H]-126.132859911
AllCCS[M+HCOO]-129.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Itaconic acidOC(=O)CC(=C)C(O)=O2010.7Standard polar33892256
Itaconic acidOC(=O)CC(=C)C(O)=O1014.5Standard non polar33892256
Itaconic acidOC(=O)CC(=C)C(O)=O1292.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Itaconic acid,1TMS,isomer #1C=C(CC(=O)O[Si](C)(C)C)C(=O)O1296.5Semi standard non polar33892256
Itaconic acid,1TMS,isomer #2C=C(CC(=O)O)C(=O)O[Si](C)(C)C1268.0Semi standard non polar33892256
Itaconic acid,2TMS,isomer #1C=C(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1362.2Semi standard non polar33892256
Itaconic acid,1TBDMS,isomer #1C=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O1528.8Semi standard non polar33892256
Itaconic acid,1TBDMS,isomer #2C=C(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C1502.8Semi standard non polar33892256
Itaconic acid,2TBDMS,isomer #1C=C(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1786.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Itaconic acid GC-MS (2 TMS)splash10-067j-4970000000-62c083c1889c0389bdc72014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Itaconic acid GC-MS (Non-derivatized)splash10-067j-4970000000-62c083c1889c0389bdc72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Itaconic acid GC-EI-TOF (Non-derivatized)splash10-0002-1910000000-691ec6088f9d55e9b1582017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Itaconic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-001c-9100000000-3218ae9ee6b97674a0392016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Itaconic acid GC-MS (2 TMS) - 70eV, Positivesplash10-059i-9420000000-cf91095ef1210525cf5d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Itaconic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Itaconic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-03y1-9400000000-8522d5eb5288a63433b12012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-00kr-9000000000-8287612bcdd337cb94dd2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-02a9-9200000000-d17287465b81dab7939c2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-004i-4900000000-8433e22f39cee33233c12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-000i-9000000000-5879e62dedd6aab4b1ca2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-000i-9000000000-464f41418a542f68cdb22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-0006-9000000000-96ec7055deb2e04029432012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-0006-9000000000-f4499898bdcf9c9eb9c42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-000i-9100000000-dac578cf4d95b2206d4b2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QQ , negative-QTOFsplash10-004i-4900000000-8433e22f39cee33233c12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-5879e62dedd6aab4b1ca2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QQ , negative-QTOFsplash10-000i-9000000000-464f41418a542f68cdb22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-96ec7055deb2e04029432017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9000000000-f4499898bdcf9c9eb9c42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid LC-ESI-QTOF , negative-QTOFsplash10-000i-9100000000-dac578cf4d95b2206d4b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid 40V, Negative-QTOFsplash10-0006-9000000000-3a323040e2c2c85076cf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid 35V, Negative-QTOFsplash10-000i-9000000000-d3d15eaac40f45cd1f122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid 6V, Negative-QTOFsplash10-000i-9000000000-2834a749f71c5924616c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Itaconic acid 10V, Negative-QTOFsplash10-000i-9000000000-b8ad1fa3bcacc46e663c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconic acid 10V, Positive-QTOFsplash10-03di-4900000000-8dbdce71f36577627d672015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconic acid 20V, Positive-QTOFsplash10-02g9-9300000000-72767f1807dfa80e809c2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconic acid 40V, Positive-QTOFsplash10-00kf-9000000000-e26167424a1c652a920d2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconic acid 10V, Negative-QTOFsplash10-004r-5900000000-95e66a8f3b6c0bc3cec62015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconic acid 20V, Negative-QTOFsplash10-002r-9500000000-c8ab0cb1983e8213e6222015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Itaconic acid 40V, Negative-QTOFsplash10-014u-9000000000-f54d12caffc54c552d2d2015-05-27Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Blood
  • Sweat
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SweatDetected but not QuantifiedNot QuantifiedAdult BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012645
KNApSAcK IDC00033964
Chemspider ID789
KEGG Compound IDC00490
BioCyc IDITACONATE
BiGG ID35130
Wikipedia LinkItaconic_acid
METLIN ID6483
PubChem Compound811
PDB IDNot Available
ChEBI ID30838
Food Biomarker OntologyNot Available
VMH IDITACON
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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 ]
  2. Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8. [PubMed:26360870 ]

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