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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-08 16:27:04 UTC
Update Date2022-11-30 19:24:23 UTC
HMDB IDHMDB0112131
Secondary Accession NumbersNone
Metabolite Identification
Common NameFAHFA(18:0/10-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(18:0/10-O-18:0), in particular, is formed from the condensation of the carboxy group of stearic acid with the hydroxy group of 10-hydroxyoctadecanoic acid. It is alternatively named 10-SAHSA since it is the 10-hydroxy isomer of the SAHSA (stearic acid-hydroxystearic acid) family.
Structure
Thumb
Synonyms
ValueSource
10-SAHSAHMDB
10-[(1-Oxooctadecyl)oxy]-octadecanoic acidHMDB
10-(Stearoyloxy)octadecanoic acidHMDB
10-(Stearoyloxy)stearic acidHMDB
Stearic acid-10-hydroxystearic acidHMDB
FAHFA(18:0/10-O-18:0)SMPDB
Chemical FormulaC36H70O4
Average Molecular Weight566.952
Monoisotopic Molecular Weight566.527410734
IUPAC Name10-(octadecanoyloxy)octadecanoic acid
Traditional Name10-(octadecanoyloxy)octadecanoic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC(CCCCCCCC)CCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C36H70O4/c1-3-5-7-9-11-12-13-14-15-16-17-18-19-25-29-33-36(39)40-34(30-26-22-10-8-6-4-2)31-27-23-20-21-24-28-32-35(37)38/h34H,3-33H2,1-2H3,(H,37,38)
InChI KeyKARVIOOFYPUCOA-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
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
Predicted Chromatographic Properties
Spectra
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 ID57621601
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101527491
PDB IDNot Available
ChEBI IDNot Available
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 ]
  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.