You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2019-07-23 07:12:38 UTC
HMDB IDHMDB0059633
Secondary Accession Numbers
  • HMDB59633
Metabolite Identification
Common Name(9S,10S)-9,10-dihydroxyoctadecanoate
Description(9S,10S)-9,10-dihydroxyoctadecanoate, also known as (S,S)-9,10-dihydroxystearic acid or (9S,10S)-dihydroxystearate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms (9S,10S)-9,10-dihydroxyoctadecanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563865958
Synonyms
ValueSource
(9S,10S)-9,10-Dihydroxystearic acidChEBI
(9S,10S)-Dihydroxdyoctadecanoic acidChEBI
(9S,10S)-Dihydroxystearic acidChEBI
(S,S)-9,10-Dihydroxystearic acidChEBI
(9S,10S)-9,10-DihydroxystearateGenerator
(9S,10S)-DihydroxdyoctadecanoateGenerator
(9S,10S)-DihydroxystearateGenerator
(S,S)-9,10-DihydroxystearateGenerator
(9S,10S)-9,10-Dihydroxyoctadecanoic acidGenerator
(9S,10S)-9,10-DihydroxyoctadecanoateGenerator
Chemical FormulaC18H36O4
Average Molecular Weight316.476
Monoisotopic Molecular Weight316.26135964
IUPAC Name(9S,10S)-9,10-dihydroxyoctadecanoic acid
Traditional Name(9S,10S)-dihydroxystearic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CCCCCCCC)[C@@]([H])(O)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C18H36O4/c1-2-3-4-5-7-10-13-16(19)17(20)14-11-8-6-9-12-15-18(21)22/h16-17,19-20H,2-15H2,1H3,(H,21,22)/t16-,17-/m0/s1
InChI KeyVACHUYIREGFMSP-IRXDYDNUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Secondary alcohol
  • 1,2-diol
  • 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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

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 Solubility0.047 g/LALOGPS
logP5.27ALOGPS
logP4.68ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity89.32 m³·mol⁻¹ChemAxon
Polarizability40.17 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-7920000000-5d5f4cd379839da63600Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-9112210000-4c89c9fa67d4344f8ea6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0192000000-8aab6406655a84cf775dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-5950000000-3a7ee5e5bd1701383cf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9310000000-a53182b68f011f3ad319Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0059000000-64ea459047babba3821eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00r5-0952000000-7ec7f5e455fb1fbaf90aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-6900000000-5436f5e2916990719cfaSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15988
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12235230
PDB IDNot Available
ChEBI ID49254
Food Biomarker OntologyNot Available
VMH IDNot Available
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.

Enzymes

General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme. The C-terminal domain has epoxide hydrolase activity and acts on epoxides (alkene oxides, oxiranes) and arene oxides. Plays a role in xenobiotic metabolism by degrading potentially toxic epoxides. Also determines steady-state levels of physiological mediators. The N-terminal domain has lipid phosphatase activity, with the highest activity towards threo-9,10-phosphonooxy-hydroxy-octadecanoic acid, followed by erythro-9,10-phosphonooxy-hydroxy-octadecanoic acid, 12-phosphonooxy-octadec-9Z-enoic acid, 12-phosphonooxy-octadec-9E-enoic acid, and p-nitrophenyl phospate.
Gene Name:
EPHX2
Uniprot ID:
P34913
Molecular weight:
62615.22
Reactions
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate + Water → (9S,10S)-9,10-dihydroxyoctadecanoate + Phosphatedetails