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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 IDHMDB0059632
Secondary Accession Numbers
  • HMDB59632
Metabolite Identification
Common Name(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate
Description(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate, also known as (9S,10S)-10-hydroxy-9-(phosphonooxy)stearic acid, 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)-10-hydroxy-9-(phosphonooxy)octadecanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563865958
Synonyms
ValueSource
(9S,10S)-10-Hydroxy-9-(phosphonooxy)stearic acidChEBI
(9S,10S)-10-Hydroxy-9-(phosphonooxy)stearateGenerator
(9S,10S)-10-Hydroxy-9-(phosphonooxy)octadecanoic acidGenerator
(9S,10S)-10-Hydroxy-9-(phosphonooxy)octadecanoateGenerator
Chemical FormulaC18H37O7P
Average Molecular Weight396.4559
Monoisotopic Molecular Weight396.22769005
IUPAC Name(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid
Traditional Name(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CCCCCCCC)[C@]([H])(CCCCCCCC(O)=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C18H37O7P/c1-2-3-4-5-7-10-13-16(19)17(25-26(22,23)24)14-11-8-6-9-12-15-18(20)21/h16-17,19H,2-15H2,1H3,(H,20,21)(H2,22,23,24)/t16-,17-/m0/s1
InChI KeyUELBXEKQONEDKM-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
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • 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 Solubility0.034 g/LALOGPS
logP3.19ALOGPS
logP4.56ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)1.56ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity100.19 m³·mol⁻¹ChemAxon
Polarizability44.27 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]+194.85831661259
DarkChem[M-H]-191.55931661259
DeepCCS[M+H]+201.16130932474
DeepCCS[M-H]-198.80430932474
DeepCCS[M-2H]-231.6930932474
DeepCCS[M+Na]+207.28530932474
AllCCS[M+H]+204.932859911
AllCCS[M+H-H2O]+202.532859911
AllCCS[M+NH4]+207.032859911
AllCCS[M+Na]+207.632859911
AllCCS[M-H]-196.732859911
AllCCS[M+Na-2H]-198.332859911
AllCCS[M+HCOO]-200.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate[H][C@](O)(CCCCCCCC)[C@]([H])(CCCCCCCC(O)=O)OP(O)(O)=O4167.6Standard polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate[H][C@](O)(CCCCCCCC)[C@]([H])(CCCCCCCC(O)=O)OP(O)(O)=O2661.7Standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate[H][C@](O)(CCCCCCCC)[C@]([H])(CCCCCCCC(O)=O)OP(O)(O)=O3069.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,1TMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O)OP(=O)(O)O2948.4Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,1TMS,isomer #2CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)OP(=O)(O)O2963.4Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,1TMS,isomer #3CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O)OP(=O)(O)O[Si](C)(C)C2966.3Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,2TMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)OP(=O)(O)O2971.4Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,2TMS,isomer #2CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O)OP(=O)(O)O[Si](C)(C)C3001.6Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,2TMS,isomer #3CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C3013.4Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,2TMS,isomer #4CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3025.9Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,3TMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C3017.9Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,3TMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C2939.9Standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,3TMS,isomer #2CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3037.3Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,3TMS,isomer #2CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2908.8Standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,3TMS,isomer #3CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3039.5Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,3TMS,isomer #3CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2972.8Standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,4TMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3040.0Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,4TMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2963.3Standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,1TBDMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O)OP(=O)(O)O3193.5Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,1TBDMS,isomer #2CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O3233.9Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,1TBDMS,isomer #3CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O)OP(=O)(O)O[Si](C)(C)C(C)(C)C3200.1Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,2TBDMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O3474.5Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,2TBDMS,isomer #2CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O)OP(=O)(O)O[Si](C)(C)C(C)(C)C3471.9Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,2TBDMS,isomer #3CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C3492.3Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,2TBDMS,isomer #4CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3500.2Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,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)OP(=O)(O)O[Si](C)(C)C(C)(C)C3709.2Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,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)OP(=O)(O)O[Si](C)(C)C(C)(C)C3377.0Standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,3TBDMS,isomer #2CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3727.8Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,3TBDMS,isomer #2CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3306.1Standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,3TBDMS,isomer #3CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3733.1Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,3TBDMS,isomer #3CCCCCCCC[C@H](O)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3392.3Standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,4TBDMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3940.5Semi standard non polar33892256
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate,4TBDMS,isomer #1CCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3485.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9140000000-57a45a486d019f91319c2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate GC-MS (2 TMS) - 70eV, Positivesplash10-002b-9002110000-a05c9947f0aa36c253282017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 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)-10-hydroxy-9-(phosphonooxy)octadecanoate 10V, Positive-QTOFsplash10-005a-1198000000-8090815685ceaa808f892017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 20V, Positive-QTOFsplash10-0002-9842000000-901ede46ae52d269eac52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 40V, Positive-QTOFsplash10-052b-9440000000-4434b56f8adab06ef65e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 10V, Negative-QTOFsplash10-002b-4009000000-4b52fa6e6d5e1939c0b52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 20V, Negative-QTOFsplash10-004i-9003000000-86561a38430f366338f92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 40V, Negative-QTOFsplash10-004i-9000000000-bad73b646e4cf4886df62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 10V, Positive-QTOFsplash10-002b-0079000000-b2eefcdaaadd39af3da62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 20V, Positive-QTOFsplash10-001j-0390000000-b7d88dc35abac563620d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 40V, Positive-QTOFsplash10-0a59-9520000000-8abe2e4dea0864f7fa142021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 10V, Negative-QTOFsplash10-002b-9003000000-b7ec46af0de489e8e07a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 20V, Negative-QTOFsplash10-004i-9000000000-7ee19e8863bc7dbe54462021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate 40V, Negative-QTOFsplash10-004i-9000000000-cf5100d370b03550ae4b2021-09-25Wishart 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 IDC15989
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23724633
PDB IDNot Available
ChEBI ID49253
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