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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-07-25 00:02:28 UTC
Update Date2017-10-23 19:06:06 UTC
HMDB IDHMDB0012535
Secondary Accession Numbers
  • HMDB12535
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
ValueSource
12-HHTrEChEBI
12S-Hydroxy-5Z,8E,10E-heptadecatrienoic acidChEBI
12S-Hydroxy-5Z,8E,10E-heptadecatrienoateGenerator
12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoateHMDB
12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoic acidHMDB
12(S)-Hydroxy-(5Z,8Z,10E)-heptadeca-5,8,10-trienoic acid anionHMDB
12-HydroxyheptadecatrienoateHMDB
12-Hydroxyheptadecatrienoic acidHMDB
HHTHMDB
HydroxyheptadecatrienateHMDB
HydroxyheptadecatrienoateHMDB
Hydroxyheptadecatrienoic acidHMDB
Hydroxyheptadecatrienoic acid anionHMDB
12-L-Hydroxy-5,8,10-heptadecatrienoic acidMeSH
12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-isomerMeSH
12-HHTMeSH
12-Hydroxy-5,8,10-heptadecatrienoic acidMeSH
12-Hydroxy-5,8,10-heptadecatrienoic acid, (e,Z,Z)-isomerMeSH
12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-(e,Z,Z)-isomerMeSH
12-Hydroxy-5,8,10-heptadecatrienoic acid, (S)-(Z,e,e)-isomerMeSH
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 chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLong-chain 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical 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 Solubility0.015 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity86.55 m³·mol⁻¹ChemAxon
Polarizability34.15 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-7940000000-88adc904734528989f76View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-009i-9223100000-1505e4bf1a2b098cc662View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-025c6c4f9cc74b291b50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-044s-4490000000-e7b3a17b02d9bf372212View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05tf-9510000000-a08ec733ca2fb7d71708View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-0cc456c0c372dc9dcfc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-1090000000-a3df181a56e24018b9e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9320000000-f4709ec871502770402eView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283141
PDB IDNot Available
ChEBI ID63977
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.