ChemFOnt: Showing chemical card for 11(R)-HPETE (CFc000002179)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:00 UTC

Chemfont ID

CFc000002179

Molecule Identification

Common Name

11(R)-HPETE

Definition

11R-HPETE is a hydroperoxyeicosatetraenoic acid eicosanoid derived from arachidonic acid. 11R-HPETE is formed from arachidonic acid in the prostaglandin endoperoxide H synthase-1 cyclooxygenase site. 11R-HPETE has been described in other mammalian tissues (rat, sheep). There are two distinct isozymes of prostaglandin H synthase (PGHS), the key enzyme in prostaglandin biosynthesis; PGHS-1 is generally considered to play a housekeeping role, whereas PGHS-2 has been linked to various pathological processes. Both PGHS isozymes have two catalytic activities; they are a cyclooxygenase activity that converts arachidonic acid (AA) to prostaglandin G2 (PGG2) and a peroxidase activity that catalyzes the transformation of PGG2 to prostaglandin H2. Oxygenase activity is completely abolished in aspirin-treated PGHS-1 (ASA-PGHS-1), whereas aspirin-treated PGHS-2 (ASA-PGHS-2) still catalyzes formation of 11(R)-HPETE. (PMID: 12664566 , 15292194 , 15964853 , 12167656 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(11R,12E)-11-hydroperoxyicosa-5,8,12,14-tetraenoic acid

Traditional Name

(11R,12E)-11-hydroperoxyicosa-5,8,12,14-tetraenoic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-4-5-7-10-13-16-19(24-23)17-14-11-8-6-9-12-15-18-20(21)22/h6-7,9-11,13-14,16,19,23H,2-5,8,12,15,17-18H2,1H3,(H,21,22)/b9-6?,10-7?,14-11?,16-13+/t19-/m0/s1

InChI Key

PCGWZQXAGFGRTQ-BTAHDKLUSA-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

Extracellular (HMDB: HMDB0004696)
Membrane (HMDB: HMDB0004696)

Source

Exogenous

Exogenous (HMDB: HMDB0004696)

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: HMDB0004696)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	5.89	ALOGPS
logP	5.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.82	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

FDB023411

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

Not Available

Showing chemical card for 11(R)-HPETE (CFc000002179)

MOL for CFc000002179 (11(R)-HPETE)

3D MOL for CFc000002179 (11(R)-HPETE)

3D SDF for CFc000002179 (11(R)-HPETE)

3D-SDF for CFc000002179 (11(R)-HPETE)

PDB for CFc000002179 (11(R)-HPETE)

3D PDB for CFc000002179 (11(R)-HPETE)

SMILES for CFc000002179 (11(R)-HPETE)

INCHI for CFc000002179 (11(R)-HPETE)

Structure for CFc000002179 (11(R)-HPETE)

3D Structure for CFc000002179 (11(R)-HPETE)