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Record Information
Version3.6
Creation Date2009-07-25 00:02:28 UTC
Update Date2015-03-09 22:57:40 UTC
HMDB IDHMDB12535
Secondary Accession NumbersNone
Metabolite Identification
Common Name12S-HHT
Description12(S)-HHTrE is an unusual product of the cyclooxygenase (COX) pathway and one of the primary arachidonic acid metabolites of the human platelet.1 It is biosynthesized by thromboxane (TX) synthesis from prostaglandin H2 (PGH2) concurrently with TXA2. The biological role of 12(S)-HHTrE is uncertain. It is avidly oxidized to 12-oxoHTrE by porcine 15-hydroxy PGDH.
Structure
Thumb
Synonyms
  1. 12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoate
  2. 12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoic acid
  3. 12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoic acid anion
  4. 12-HHTre
  5. 12-Hydroxyheptadecatrienoate
  6. 12-Hydroxyheptadecatrienoic acid
  7. HHT
  8. Hydroxyheptadecatrienate
  9. Hydroxyheptadecatrienoate
  10. Hydroxyheptadecatrienoic acid
  11. Hydroxyheptadecatrienoic acid anion
Chemical FormulaC17H28O3
Average Molecular Weight280.4024
Monoisotopic Molecular Weight280.203844762
IUPAC Name(5Z,8E,10E,12S)-12-hydroxyheptadeca-5,8,10-trienoic acid
Traditional Name12-HHTrE
CAS Registry Number54397-84-1
SMILES
CCCCC[C@H](O)\C=C\C=C\C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C17H28O3/c1-2-3-10-13-16(18)14-11-8-6-4-5-7-9-12-15-17(19)20/h5-8,11,14,16,18H,2-4,9-10,12-13,15H2,1H3,(H,19,20)/b7-5-,8-6+,14-11+/t16-/m0/s1
InChI KeyKUKJHGXXZWHSBG-WBGSEQOASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility0.015 mg/mLALOGPS
logP4.99ALOGPS
logP4.38ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity86.55 m3·mol-1ChemAxon
Polarizability34.15 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00203 +/- 0.000278 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029115
KNApSAcK IDNot Available
Chemspider ID4446265
KEGG Compound IDNot Available
BioCyc ID1-KETO-2-METHYLVALERATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12535
Metagene LinkHMDB12535
METLIN IDNot Available
PubChem Compound5283141
PDB IDNot Available
ChEBI ID63977
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available