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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2022-03-07 03:17:34 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.73231661259
DarkChem[M-H]-178.21631661259
DeepCCS[M+H]+182.29230932474
DeepCCS[M-H]-179.93430932474
DeepCCS[M-2H]-212.81930932474
DeepCCS[M+Na]+188.38630932474
AllCCS[M+H]+189.432859911
AllCCS[M+H-H2O]+186.632859911
AllCCS[M+NH4]+191.932859911
AllCCS[M+Na]+192.732859911
AllCCS[M-H]-183.132859911
AllCCS[M+Na-2H]-184.332859911
AllCCS[M+HCOO]-185.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(9S,10S)-9,10-dihydroxyoctadecanoate[H][C@](O)(CCCCCCCC)[C@@]([H])(O)CCCCCCCC(O)=O3928.7Standard polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate[H][C@](O)(CCCCCCCC)[C@@]([H])(O)CCCCCCCC(O)=O2436.6Standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate[H][C@](O)(CCCCCCCC)[C@@]([H])(O)CCCCCCCC(O)=O2530.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(9S,10S)-9,10-dihydroxyoctadecanoate,1TMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C)[C@@H](O)CCCCCCCC(=O)O2516.7Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,1TMS,isomer #2CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C2519.0Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,1TMS,isomer #3CCCCCCCC[C@H](O)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C2558.1Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,2TMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C2555.5Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,2TMS,isomer #2CCCCCCCC[C@H](O[Si](C)(C)C)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C2572.4Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,2TMS,isomer #3CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2574.3Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,3TMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2621.1Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,1TBDMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCCCCCC(=O)O2760.3Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,1TBDMS,isomer #2CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C2761.1Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,1TBDMS,isomer #3CCCCCCCC[C@H](O)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2812.0Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,2TBDMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3072.0Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,2TBDMS,isomer #2CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3078.0Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,2TBDMS,isomer #3CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3077.4Semi standard non polar33892256
(9S,10S)-9,10-dihydroxyoctadecanoate,3TBDMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3360.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dm-7920000000-5d5f4cd379839da636002017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate GC-MS (3 TMS) - 70eV, Positivesplash10-014i-9112210000-4c89c9fa67d4344f8ea62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 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 - (9S,10S)-9,10-dihydroxyoctadecanoate 10V, Positive-QTOFsplash10-0002-0192000000-8aab6406655a84cf775d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 20V, Positive-QTOFsplash10-03ea-5950000000-3a7ee5e5bd1701383cf42017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 40V, Positive-QTOFsplash10-052f-9310000000-a53182b68f011f3ad3192017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 10V, Negative-QTOFsplash10-014i-0059000000-64ea459047babba3821e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 20V, Negative-QTOFsplash10-00r5-0952000000-7ec7f5e455fb1fbaf90a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 40V, Negative-QTOFsplash10-0a4l-6900000000-5436f5e2916990719cfa2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 10V, Positive-QTOFsplash10-000t-0191000000-e4d08971240d043896d72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 20V, Positive-QTOFsplash10-05u2-9880000000-5070a163721cdae8d9f92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 40V, Positive-QTOFsplash10-0a59-9200000000-cf5b50915d51f39d14432021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 10V, Negative-QTOFsplash10-014i-0029000000-2b51d6a4632977033c102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 20V, Negative-QTOFsplash10-014j-0797000000-ae27ab91a61b2dd99b592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-9,10-dihydroxyoctadecanoate 40V, Negative-QTOFsplash10-00bd-4951000000-8528023e01bfc86076282021-09-22Wishart LabView Spectrum
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
FooDB 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
MarkerDB IDNot Available
Good Scents 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