ChemFOnt: Showing chemical card for 8,15-DiHETE (CFc000006228)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:09 UTC

Chemfont ID

CFc000006228

Molecule Identification

Common Name

8,15-DiHETE

Definition

8,15-DiHETE is a double oxidation product of arachadonic acid. It is generated through the action of 15-lipoxygenase (PMID: 8334154 ). 8,15-DiHETE is also known as eosinophil chemotactic factor of anaphylaxis (ECF-A). In particular it is able to selectively attract eosinophils and neutrophils from mixed leukocyte populations.Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₄

Average Molecular Weight

336.4657

Monoisotopic Molecular Weight

336.230059512

IUPAC Name

(9E)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid

Traditional Name

(9E)-8,15-dihydroxyicosa-5,9,11,13-tetraenoic acid

CAS Registry Number

77667-08-4

SMILES

CCCCCC(O)C=CC=C\C=C\C(O)CC=CCCCC(O)=O

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-8-13-18(21)14-9-4-5-10-15-19(22)16-11-6-7-12-17-20(23)24/h4-6,9-11,14-15,18-19,21-22H,2-3,7-8,12-13,16-17H2,1H3,(H,23,24)/b5-4?,11-6?,14-9?,15-10+

InChI Key

NNPWRKSGORGTIM-RIRWYGNESA-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
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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: HMDB0010219)

Source

Endogenous

Endogenous (HMDB: HMDB0010219)

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)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	5.37	ALOGPS
logP	4.13	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	102.98 m³·mol⁻¹	ChemAxon
Polarizability	41.35 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

FDB027372

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 8,15-DiHETE (CFc000006228)

MOL for CFc000006228 (8,15-DiHETE)

3D MOL for CFc000006228 (8,15-DiHETE)

3D SDF for CFc000006228 (8,15-DiHETE)

3D-SDF for CFc000006228 (8,15-DiHETE)

PDB for CFc000006228 (8,15-DiHETE)

3D PDB for CFc000006228 (8,15-DiHETE)

SMILES for CFc000006228 (8,15-DiHETE)

INCHI for CFc000006228 (8,15-DiHETE)

Structure for CFc000006228 (8,15-DiHETE)

3D Structure for CFc000006228 (8,15-DiHETE)