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Record Information
Version5.0
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
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.73 g/LALOGPS
logP10(-0.2) g/LALOGPS
logP10(-0.076) g/LChemAxon
logS10(-1.7) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.49131661259
DarkChem[M-H]-137.60931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(Z)-But-1-ene-1,2,4-tricarboxylate,1TMS,#1C[Si](C)(C)OC(=O)CC/C(=C/C(=O)O)C(=O)O1834.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,1TMS,#2C[Si](C)(C)OC(=O)/C=C(/CCC(=O)O)C(=O)O1828.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,1TMS,#3C[Si](C)(C)OC(=O)/C(=C\C(=O)O)CCC(=O)O1799.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,2TMS,#1C[Si](C)(C)OC(=O)/C=C(/CCC(=O)O[Si](C)(C)C)C(=O)O1902.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,2TMS,#2C[Si](C)(C)OC(=O)CC/C(=C/C(=O)O)C(=O)O[Si](C)(C)C1866.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,2TMS,#3C[Si](C)(C)OC(=O)/C=C(/CCC(=O)O)C(=O)O[Si](C)(C)C1861.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,3TMS,#1C[Si](C)(C)OC(=O)/C=C(/CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C1860.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CC/C(=C/C(=O)O)C(=O)O2078.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,1TBDMS,#2CC(C)(C)[Si](C)(C)OC(=O)/C=C(/CCC(=O)O)C(=O)O2080.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,1TBDMS,#3CC(C)(C)[Si](C)(C)OC(=O)/C(=C\C(=O)O)CCC(=O)O2074.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,2TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)/C=C(/CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O2382.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,2TBDMS,#2CC(C)(C)[Si](C)(C)OC(=O)CC/C(=C/C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2334.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,2TBDMS,#3CC(C)(C)[Si](C)(C)OC(=O)/C=C(/CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C2306.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
(Z)-But-1-ene-1,2,4-tricarboxylate,3TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)/C=C(/CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2509.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-But-1-ene-1,2,4-tricarboxylate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4900000000-38a9e722b0988b241dc32016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-But-1-ene-1,2,4-tricarboxylate GC-MS (3 TMS) - 70eV, Positivesplash10-00dr-7089000000-9f148b326ce9aaba25ad2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-But-1-ene-1,2,4-tricarboxylate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-But-1-ene-1,2,4-tricarboxylate 10V, Positive-QTOFsplash10-0fmu-0900000000-8ab76514ec0d07fd32212016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-But-1-ene-1,2,4-tricarboxylate 20V, Positive-QTOFsplash10-004m-4900000000-60edfaa1db48a2d009882016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-But-1-ene-1,2,4-tricarboxylate 40V, Positive-QTOFsplash10-0002-9200000000-7c8f91321a4901f02bb22016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-But-1-ene-1,2,4-tricarboxylate 10V, Negative-QTOFsplash10-000f-1900000000-05cedaf9edcf6100ea3a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-But-1-ene-1,2,4-tricarboxylate 20V, Negative-QTOFsplash10-0007-3900000000-13f3f7df422ca12f84e62016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-But-1-ene-1,2,4-tricarboxylate 40V, Negative-QTOFsplash10-05mp-9400000000-e1137100ffdd5a6e71862016-09-12Wishart 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 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
MarkerDB IDNot Available
Good Scents 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