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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-09-08 16:26:06 UTC
Update Date2019-07-23 09:13:40 UTC
HMDB IDHMDB0112128
Secondary Accession NumbersNone
Metabolite Identification
Common NameFAHFA(18:0/5-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(18:0/5-O-18:0), in particular, is formed from the condensation of the carboxy group of stearic acid with the hydroxy group of 5-hydroxyoctadecanoic acid. It is alternatively named 5-SAHSA since it is the 5-hydroxy isomer of the SAHSA (stearic acid-hydroxystearic acid) family.
Structure
Data?1563873220
Synonyms
ValueSource
5-SAHSASMPDB, HMDB
5-[(1-oxooctadecyl)oxy]-octadecanoic acidSMPDB, HMDB
5-(stearoyloxy)octadecanoic acidSMPDB, HMDB
5-(stearoyloxy)stearic acidSMPDB, HMDB
stearic acid-5-hydroxystearic acidSMPDB, HMDB
FAHFA(18:0/5-O-18:0)SMPDB
Chemical FormulaC36H70O4
Average Molecular Weight566.952
Monoisotopic Molecular Weight566.527410734
IUPAC Name5-(octadecanoyloxy)octadecanoic acid
Traditional Name5-(octadecanoyloxy)octadecanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCCCC)CCCC(O)=O
InChI Identifier
InChI=1S/C36H70O4/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-33-36(39)40-34(31-29-32-35(37)38)30-27-25-23-21-19-14-12-10-8-6-4-2/h34H,3-33H2,1-2H3,(H,37,38)
InChI KeyBSOQNRNPFJEDMC-UHFFFAOYSA-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

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
logP10.21ALOGPS
logP13.57ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)4.44ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity170.75 m³·mol⁻¹ChemAxon
Polarizability76.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-9164373000-b0c36e2cc9007b91d9a3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00m0-6193720000-23c3b82654634f47c539Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00l2-0050090000-c51fcfdc977f53df16b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015j-0190020000-0155c90187a7941323d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0076-3390100000-79f119cdd18c011b60e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0040090000-739d34fe1de0248cd73fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00l2-1090040000-5f8889b08de2b0ccf597Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5d-4190000000-a472cc32894172760b5eSpectrum
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 Compound101527487
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.