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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:53:27 UTC
Update Date2019-07-23 07:14:03 UTC
HMDB IDHMDB0060320
Secondary Accession Numbers
  • HMDB60320
Metabolite Identification
Common Name(Z)-But-1-ene-1,2,4-tricarboxylate
Description(Z)-But-1-ene-1,2,4-tricarboxylate, also known as (Z)-1,2,4-but-1-enetricarboxylic acid or cis-homoaconitate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups (Z)-But-1-ene-1,2,4-tricarboxylate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (Z)-But-1-ene-1,2,4-tricarboxylate exists in all living species, ranging from bacteria to humans. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof).
Structure
Data?1563866043
Synonyms
ValueSource
(Z)-1,2,4-But-1-enetricarboxylic acidChEBI
But-1-ene-1,2,4-tricarboxylateChEBI
cis-HomoaconitateChEBI
Homo-cis-aconitateChEBI
(Z)-1,2,4-But-1-enetricarboxylateGenerator
But-1-ene-1,2,4-tricarboxylic acidGenerator
cis-Homoaconitic acidGenerator
Homo-cis-aconitic acidGenerator
(Z)-But-1-ene-1,2,4-tricarboxylic acidGenerator
Chemical FormulaC7H8O6
Average Molecular Weight188.1348
Monoisotopic Molecular Weight188.032087988
IUPAC Name(1Z)-but-1-ene-1,2,4-tricarboxylic acid
Traditional Namehomo-cis-aconitate
CAS Registry NumberNot Available
SMILES
OC(=O)CC\C(=C\C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H8O6/c8-5(9)2-1-4(7(12)13)3-6(10)11/h3H,1-2H2,(H,8,9)(H,10,11)(H,12,13)/b4-3-
InChI KeyBJYPZFUWWJSAKC-ARJAWSKDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.73 g/LALOGPS
logP-0.2ALOGPS
logP-0.076ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.28ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.83 m³·mol⁻¹ChemAxon
Polarizability16.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4900000000-38a9e722b0988b241dc3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00dr-7089000000-9f148b326ce9aaba25adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fmu-0900000000-8ab76514ec0d07fd3221Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004m-4900000000-60edfaa1db48a2d00988Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9200000000-7c8f91321a4901f02bb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-1900000000-05cedaf9edcf6100ea3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-3900000000-13f3f7df422ca12f84e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mp-9400000000-e1137100ffdd5a6e7186Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444242
KEGG Compound IDC04002
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280640
PDB IDNot Available
ChEBI ID17516
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:
ACO2
Uniprot ID:
Q99798
Molecular weight:
85424.745
Reactions
Homocitric acid → (Z)-But-1-ene-1,2,4-tricarboxylate + Waterdetails
General function:
Involved in metabolic process
Specific function:
Iron sensor. Binds a 4Fe-4S cluster and functions as aconitase when cellular iron levels are high. Functions as mRNA binding protein that regulates uptake, sequestration and utilization of iron when cellular iron levels are low. Binds to iron-responsive elements (IRES) in target mRNA species when iron levels are low. Binding of a 4Fe-4S cluster precludes RNA binding. Catalyzes the isomerization of citrate to isocitrate via cis-aconitate (By similarity).
Gene Name:
ACO1
Uniprot ID:
P21399
Molecular weight:
98398.14
Reactions
Homocitric acid → (Z)-But-1-ene-1,2,4-tricarboxylate + Waterdetails