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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-11-30 15:52:45 UTC
Update Date2019-07-23 05:58:43 UTC
HMDB IDHMDB0013312
Secondary Accession Numbers
  • HMDB13312
Metabolite Identification
Common Nametrans-3-Octenedioic acid
Descriptiontrans-3-Octenedioic acid, also known as trans-3-octene -1,8-dioate, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. trans-3-Octenedioic acid is a weakly acidic compound (based on its pKa).
Structure
Data?1563861523
Synonyms
ValueSource
trans-3-OctenedioateGenerator
trans-3-Octene -1,8-dioateHMDB
trans-3-Octene -1,8-dioic acidHMDB
trans-3-Octene-1,8-dioiateHMDB
trans-3-OctenedioiateHMDB
(3E)-Oct-3-enedioateGenerator
Chemical FormulaC8H12O4
Average Molecular Weight172.1785
Monoisotopic Molecular Weight172.073558872
IUPAC Name(3E)-oct-3-enedioic acid
Traditional Name(3E)-oct-3-enedioic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCC\C=C\CC(O)=O
InChI Identifier
InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h1,3H,2,4-6H2,(H,9,10)(H,11,12)/b3-1+
InChI KeyQWWZNXBOJLOHGI-HNQUOIGGSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain 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 DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.04 g/LALOGPS
logP1.01ALOGPS
logP1.02ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability17.52 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-9200000000-9bda4daccea0c94ba554JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006t-9730000000-4a24977789b6226b0490JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0900000000-80506768aa9d594be0c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-3900000000-e85beb2bb9f54e7ddd6eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc0-9100000000-1b6622424a44ba223729JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-3b5890274a618a3778b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0900000000-86dcd0e893c03155a7b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-8392a616f5e3f797f3c7JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
UrineDetected and Quantified0.197 +/- 0.394 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
UrineDetected and Quantified1.313 +/- 1.970 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
UrineDetected and Quantified22.983 +/- 19.699 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
UrineDetected and Quantified4.597 +/- 3.283 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
UrineDetected and Quantified7.223 +/- 1.970 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified0 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified5.91 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified21.669 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
UrineDetected and Quantified65.664 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Medium Chain Acyl-CoA Dehydrogenase Deficiency
details
Associated Disorders and Diseases
Disease References
Medium Chain Acyl-CoA Dehydrogenase Deficiency
  1. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]
Associated OMIM IDs
  • 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029376
KNApSAcK IDNot Available
Chemspider ID11431462
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound22495178
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jin SJ, Tserng KY: Metabolic origins of urinary unsaturated dicarboxylic acids. Biochemistry. 1990 Sep 18;29(37):8540-7. [PubMed:2271537 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.