ChemFOnt: Showing chemical card for 13-L-Hydroperoxylinoleic acid (CFc000001981)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:45 UTC

Chemfont ID

CFc000001981

Molecule Identification

Common Name

13-L-Hydroperoxylinoleic acid

Definition

13-L-Hydroperoxylinoleic acid (13(S)-HPODE) is one of the primary products of the major polyunsaturated fatty acids (linoleic acid and arachidonic acid) from the 15-lipoxygenase pathway (EC 1.13.11.31). 13(S)-HPODE is a rather unstable metabolite and is rapidly metabolized to more stable secondary products such as diverse forms of hydroxy fatty acids (via reduction of the hydroperoxy group), alkoxy radicals (via homolytic cleavage of the peroxy group), forms of dihydro(pero)xy fatty acids (via lipoxygenase-catalysed double and triple oxygenation), or epoxy leukotrienes (via a hydrogen abstraction from a doubly allylic methylene group and a homolytic cleavage of the hydroperoxy group) (PMID: 9082450 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
13-L-Hydroperoxylinoleate	Generator

Chemical Formula

C₁₈H₃₂O₄

Average Molecular Weight

312.4443

Monoisotopic Molecular Weight

312.230059512

IUPAC Name

(13S)-13-hydroperoxyoctadeca-9,11-dienoic acid

Traditional Name

(13S)-13-hydroperoxyoctadeca-9,11-dienoic acid

CAS Registry Number

33964-75-9

SMILES

[H][C@@](CCCCC)(OO)C=CC=CCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O4/c1-2-3-11-14-17(22-21)15-12-9-7-5-4-6-8-10-13-16-18(19)20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)/t17-/m0/s1

InChI Key

JDSRHVWSAMTSSN-KRWDZBQOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Hydroperoxy fatty acid
Fatty acid
Unsaturated fatty acid
Allylic hydroperoxide
Hydroperoxide
Alkyl hydroperoxide
Peroxol
Monocarboxylic acid or derivatives
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

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Membrane (HMDB: HMDB0003871)
Extracellular (HMDB: HMDB0003871)

Source

Exogenous

Exogenous (HMDB: HMDB0003871)

Endogenous

Endogenous (HMDB: HMDB0003871)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0033 g/L	ALOGPS
logP	5.76	ALOGPS
logP	5.64	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	91.38 m³·mol⁻¹	ChemAxon
Polarizability	39.18 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023240

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440455

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Baba, N.; Yoneda, K.; Iwasa, J.; Tahara, S. Asymmetric synthesis of diacylglycerophosphocholine hydroperoxide VIa, lipoxygenase-catalyzed hydroperoxidation of linoleic acid and lipase-catalyzed enantioselective stearoylation of 2-O-benzoyl-1,3-propanediol. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1992), 31B(12), 824-7.

Showing chemical card for 13-L-Hydroperoxylinoleic acid (CFc000001981)

MOL for CFc000001981 (13-L-Hydroperoxylinoleic acid)

3D MOL for CFc000001981 (13-L-Hydroperoxylinoleic acid)

3D SDF for CFc000001981 (13-L-Hydroperoxylinoleic acid)

3D-SDF for CFc000001981 (13-L-Hydroperoxylinoleic acid)

PDB for CFc000001981 (13-L-Hydroperoxylinoleic acid)

3D PDB for CFc000001981 (13-L-Hydroperoxylinoleic acid)

SMILES for CFc000001981 (13-L-Hydroperoxylinoleic acid)

INCHI for CFc000001981 (13-L-Hydroperoxylinoleic acid)

Structure for CFc000001981 (13-L-Hydroperoxylinoleic acid)

3D Structure for CFc000001981 (13-L-Hydroperoxylinoleic acid)