ChemFOnt: Showing chemical card for 5(S)-Hydroperoxyeicosatetraenoic acid (CFc000000929)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:27 UTC

Chemfont ID

CFc000000929

Molecule Identification

Common Name

5(S)-Hydroperoxyeicosatetraenoic acid

Definition

5(S)-Hydroperoxyeicosatetraenoic acid is a lipid hydroperoxide precursor of leukotrienes. The first step of biosynthesis of leukotrienes is conversion of arachidonic acid into 5(S)-hydroperoxy-6,8,11,14-(E,Z,Z,Z)-eicosatetraenoic acid [5(S)-HpETE] by 5- lipoxygenases (5-LOX). Lipid hydroperoxides undergo homolytic decomposition into bifunctional electrophiles, which react with DNA bases to form DNA adducts. These DNA modifications are proposed to be involved in the etiology of cancer, cardiovascular disease, and neurodegeneration. 5-LOX, the enzyme responsible for the formation of 5(S)-HpETE in vivo, is expressed primarily in leukocytes, including monocytes and macrophages. Studies have implicated the 5-LOX pathway as an important mediator in the pathology of atherosclerosis. (PMID: 15777099 ). Endogenously generated 5-hydroperoxyeicosatetraenoic acid is the preferred substrate for human leukocyte leukotriene A4 synthase activity. Thus, the arachidonic acid moiety is preferentially converted to LTA4 in a concerted reaction without dissociation of a 5-HPETE intermediate. (PMID: 3036580 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5(S)-Hydroperoxyeicosatetraenoate	Generator

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(5S,6E)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid

Traditional Name

(5S,6E)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid

CAS Registry Number

71774-08-8

SMILES

[H]C(CCCCC)=C([H])CC([H])=C([H])CC([H])=C([H])C(\[H])=C(/[H])[C@]([H])(CCCC(O)=O)OO

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6?,10-9?,13-12?,16-14+/t19-/m1/s1

InChI Key

JNUUNUQHXIOFDA-MSFIICATSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroperoxyeicosatetraenoic acids

Alternative Parents

Substituents

Hydroperoxyeicosatetraenoic acid
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

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0001193)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0001193)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	5.92	ALOGPS
logP	5.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.39	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	102.82 m³·mol⁻¹	ChemAxon
Polarizability	39.98 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

FDB022480

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Dussault, Patrick; Lee, In Quen. A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE. Journal of Organic Chemistry (1995), 60(1), 218-26.

Showing chemical card for 5(S)-Hydroperoxyeicosatetraenoic acid (CFc000000929)

MOL for CFc000000929 (5(S)-Hydroperoxyeicosatetraenoic acid)

3D MOL for CFc000000929 (5(S)-Hydroperoxyeicosatetraenoic acid)

3D SDF for CFc000000929 (5(S)-Hydroperoxyeicosatetraenoic acid)

3D-SDF for CFc000000929 (5(S)-Hydroperoxyeicosatetraenoic acid)

PDB for CFc000000929 (5(S)-Hydroperoxyeicosatetraenoic acid)

3D PDB for CFc000000929 (5(S)-Hydroperoxyeicosatetraenoic acid)

SMILES for CFc000000929 (5(S)-Hydroperoxyeicosatetraenoic acid)

INCHI for CFc000000929 (5(S)-Hydroperoxyeicosatetraenoic acid)

Structure for CFc000000929 (5(S)-Hydroperoxyeicosatetraenoic acid)

3D Structure for CFc000000929 (5(S)-Hydroperoxyeicosatetraenoic acid)