ChemFOnt: Showing chemical card for FAHFA(18:0/12-O-18:0) (CFc000092529)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:03:29 UTC

Chemfont ID

CFc000092529

Molecule Identification

Common Name

FAHFA(18:0/12-O-18:0)

Definition

Branched 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(18:0/12-O-18:0), in particular, is formed from the condensation of the carboxy group of stearic acid with the hydroxy group of 12-hydroxyoctadecanoic acid. It is alternatively named 12-SAHSA since it is the 12-hydroxy isomer of the SAHSA (stearic acid-hydroxystearic acid) family.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
12-(Stearoyloxy)stearic acid	ChEBI
12-Octadecanoyloxy-octadecanoic acid	ChEBI
12-SAHSA	ChEBI
12-(Stearoyloxy)stearate	Generator
12-Octadecanoyloxy-octadecanoate	Generator
12-(Octadecanoyloxy)octadecanoate	HMDB
12-[(1-Oxooctadecyl)oxy]-octadecanoic acid	HMDB
12-(Stearoyloxy)octadecanoic acid	HMDB
Stearic acid-12-hydroxystearic acid	HMDB
FAHFA(18:0/12-O-18:0)	SMPDB, ChEBI

Chemical Formula

C₃₆H₇₀O₄

Average Molecular Weight

566.952

Monoisotopic Molecular Weight

566.527410734

IUPAC Name

12-(octadecanoyloxy)octadecanoic acid

Traditional Name

12-(octadecanoyloxy)octadecanoic acid

CAS Registry Number

51350-61-9

SMILES

CCCCCCCCCCCCCCCCCC(=O)OC(CCCCCC)CCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C36H70O4/c1-3-5-7-9-10-11-12-13-14-15-16-17-22-25-29-33-36(39)40-34(30-26-8-6-4-2)31-27-23-20-18-19-21-24-28-32-35(37)38/h34H,3-33H2,1-2H3,(H,37,38)

InChI Key

HCUIHIKPUYHKSQ-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0112120)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.5e-05 g/L	ALOGPS
logP	10.2	ALOGPS
logP	13.57	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	170.75 m³·mol⁻¹	ChemAxon
Polarizability	77.26 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0112120

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14379370

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13847803

PDB ID

Not Available

ChEBI ID

137089

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for FAHFA(18:0/12-O-18:0) (CFc000092529)

MOL for CFc000092529 (FAHFA(18:0/12-O-18:0))

3D MOL for CFc000092529 (FAHFA(18:0/12-O-18:0))

3D SDF for CFc000092529 (FAHFA(18:0/12-O-18:0))

3D-SDF for CFc000092529 (FAHFA(18:0/12-O-18:0))

PDB for CFc000092529 (FAHFA(18:0/12-O-18:0))

3D PDB for CFc000092529 (FAHFA(18:0/12-O-18:0))

SMILES for CFc000092529 (FAHFA(18:0/12-O-18:0))

INCHI for CFc000092529 (FAHFA(18:0/12-O-18:0))

Structure for CFc000092529 (FAHFA(18:0/12-O-18:0))

3D Structure for CFc000092529 (FAHFA(18:0/12-O-18:0))