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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 16:21:50 UTC
Update Date2022-03-06 22:58:33 UTC
HMDB IDHMDB0112109
Secondary Accession NumbersNone
Metabolite Identification
Common NameFAHFA(18:1(9Z)/9-O-18:0)
DescriptionBranched fatty acid esters of hydroxy fatty acids (FAHFAs) are endogenous lipids found in adipose tissue and serum that correlate with insulin sensitivity and are reduced in insulin-resistant humans. Structurally, they are characterized by a branched ester linkage between a fatty acid and a hydroxy-fatty acid. Different positions of the branched ester on the hydroxy fatty acid results in different isomers. FAHFA(18:1(9Z)/9-O-18:0), in particular, is formed from the condensation of the carboxy group of oleic acid with the hydroxy group of 9-hydroxyoctadecanoic acid. It is alternatively named 9-OAHSA since it is the 9-hydroxy isomer of the OAHSA (oleic acid-hydroxystearic acid) family.
Structure
Data?1563873218
Synonyms
ValueSource
9-(9Z-Octadecenoyloxy)-octadecanoic acidChEBI
9-(Oleoyloxy)stearic acidChEBI
9-OAHSAChEBI
FAHFA(18:1(9Z)/9-O-18:0)ChEBI
Oleic estolideChEBI
9-(9Z-Octadecenoyloxy)-octadecanoateGenerator
9-(Oleoyloxy)stearateGenerator
9-[(9Z)-Octadecenoyloxy]octadecanoateGenerator
9-(oleoyloxy)octadecanoic acidSMPDB, HMDB
oleic acid-9-hydroxystearic acidSMPDB, HMDB
Chemical FormulaC36H68O4
Average Molecular Weight564.936
Monoisotopic Molecular Weight564.51176067
IUPAC Name9-[(9Z)-octadec-9-enoyloxy]octadecanoic acid
Traditional Name9-[(9Z)-octadec-9-enoyloxy]octadecanoic acid
CAS Registry Number154086-90-5
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C36H68O4/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-25-29-33-36(39)40-34(30-26-22-19-10-8-6-4-2)31-27-23-21-24-28-32-35(37)38/h14-15,34H,3-13,16-33H2,1-2H3,(H,37,38)/b15-14-
InChI KeyPGKKGBQMNNEIHV-PFONDFGASA-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
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

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
logP10.17ALOGPS
logP13.21ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)4.62ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity171.87 m³·mol⁻¹ChemAxon
Polarizability74.7 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+248.21831661259
DarkChem[M-H]-243.3731661259
DeepCCS[M+H]+254.45330932474
DeepCCS[M-H]-252.09530932474
DeepCCS[M-2H]-286.05730932474
DeepCCS[M+Na]+261.28730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FAHFA(18:1(9Z)/9-O-18:0)[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(O)=O5064.6Standard polar33892256
FAHFA(18:1(9Z)/9-O-18:0)[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(O)=O3645.8Standard non polar33892256
FAHFA(18:1(9Z)/9-O-18:0)[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(O)=O4046.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
FAHFA(18:1(9Z)/9-O-18:0),1TMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(=O)O[Si](C)(C)C3992.1Semi standard non polar33892256
FAHFA(18:1(9Z)/9-O-18:0),1TBDMS,isomer #1CCCCCCCC/C=C\CCCCCCCC(=O)OC(CCCCCCCCC)CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C4320.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) GC-MS (1 TMS) - 70eV, Positivesplash10-0kg9-7393063000-0ebf9abb17e1f8652ec32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) GC-MS ("FAHFA(18:1(9Z)/9-O-18:0),1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) 10V, Positive-QTOFsplash10-014j-0050090000-c02d1772bee7b0ec4ede2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) 20V, Positive-QTOFsplash10-015i-0090020000-a7be3b0a45dbc2a9b1d32019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) 40V, Positive-QTOFsplash10-00rf-4290000000-9c2221c2e43c3155446f2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) 10V, Negative-QTOFsplash10-03di-0040090000-d0f6187de03492e250652019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) 20V, Negative-QTOFsplash10-01pk-0090040000-ab97c539d92bed62d3e92019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) 40V, Negative-QTOFsplash10-0a5c-4290000000-9978d47a6ff64cc1c9ef2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) 10V, Negative-QTOFsplash10-03di-0000090000-d0c7b05779e130b6f9f32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) 20V, Negative-QTOFsplash10-03di-0000090000-d0c7b05779e130b6f9f32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - FAHFA(18:1(9Z)/9-O-18:0) 40V, Negative-QTOFsplash10-03sk-0090030000-de277e22ab717964c88b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13294502
PDB IDNot Available
ChEBI ID136996
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. Yore MM, Syed I, Moraes-Vieira PM, Zhang T, Herman MA, Homan EA, Patel RT, Lee J, Chen S, Peroni OD, Dhaneshwar AS, Hammarstedt A, Smith U, McGraw TE, Saghatelian A, Kahn BB: Discovery of a class of endogenous mammalian lipids with anti-diabetic and anti-inflammatory effects. Cell. 2014 Oct 9;159(2):318-32. doi: 10.1016/j.cell.2014.09.035. [PubMed:25303528 ]