ChemFOnt: Showing chemical card for 18-Hydroxyarachidonic acid (CFc000002683)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:37 UTC

Chemfont ID

CFc000002683

Molecule Identification

Common Name

18-Hydroxyarachidonic acid

Definition

(18R)-Hydroxyarachidonate is a substrate for CYP4F8 or leukotriene-B4 20-monooxygenase (EC 1.14.13.30). This enzyme hydroxylates arachdonic acid (20:4n-6) to (18R)-hydroxyarachidonate in the endoplasmic reticulum. This reaction is irreversible. CYP4F8 is a member of the cytochrome P450 superfamily of enzymes. The cytochrome P450 proteins are monooxygenases which catalyze many reactions involved in drug metabolism and synthesis of cholesterol, steroids and other lipids. This protein localizes to the endoplasmic reticulum and functions as a 19-hydroxylase of prostaglandins in seminal vesicles. In particular, CYP4F8 catalyzes the 2-hydroxylation of PGH1 and PGH2, which will lead to biosynthesis of the two main PGs of human seminal fluid, (19R)-hydroxy-PGE1 and (19R)-hydroxy-PGE2 (PMID: 10791960 ). 18-Hydroxyarachidonic acid is an intermediate in eicosanoid metabolism.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
18-Hydroxyarachidonate	Generator

Chemical Formula

C₂₀H₃₂O₃

Average Molecular Weight

320.4663

Monoisotopic Molecular Weight

320.23514489

IUPAC Name

(18R)-18-hydroxyicosa-5,8,11,14-tetraenoic acid

Traditional Name

(18R)-18-hydroxyicosa-5,8,11,14-tetraenoic acid

CAS Registry Number

124411-81-0

SMILES

[H][C@@](O)(CC)CCC=CCC=CCC=CCC=CCCCC(O)=O

InChI Identifier

InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/t19-/m1/s1

InChI Key

PPCHNRUZQWLEMF-LJQANCHMSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatetraenoic acids

Alternative Parents

Substituents

Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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: 20671299)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0006245)

Extracellular (HMDB: HMDB0006245)
Membrane (HMDB: HMDB0006245)

Source

Exogenous

Exogenous (HMDB: HMDB0006245)

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: HMDB0006245)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	5.81	ALOGPS
logP	5.2	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	101.62 m³·mol⁻¹	ChemAxon
Polarizability	38.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

FDB023857

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

54200787

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Romanov, Stepan G.; Ivanov, Igor V.; Groza, Nataliya V.; Kuhn, Hartmut; Myagkova, Galina I. Total synthesis of (5Z,8Z,11Z,14Z)-18- and 19-oxoeicosa-5,8,11,14-tetraenoic acids. Tetrahedron (2002), 58(42), 8483-8487.

Showing chemical card for 18-Hydroxyarachidonic acid (CFc000002683)

MOL for CFc000002683 (18-Hydroxyarachidonic acid)

3D MOL for CFc000002683 (18-Hydroxyarachidonic acid)

3D SDF for CFc000002683 (18-Hydroxyarachidonic acid)

3D-SDF for CFc000002683 (18-Hydroxyarachidonic acid)

PDB for CFc000002683 (18-Hydroxyarachidonic acid)

3D PDB for CFc000002683 (18-Hydroxyarachidonic acid)

SMILES for CFc000002683 (18-Hydroxyarachidonic acid)

INCHI for CFc000002683 (18-Hydroxyarachidonic acid)

Structure for CFc000002683 (18-Hydroxyarachidonic acid)

3D Structure for CFc000002683 (18-Hydroxyarachidonic acid)