ChemFOnt: Showing chemical card for 16(17)-EpDPE (CFc000008512)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:19 UTC

Chemfont ID

CFc000008512

Molecule Identification

Common Name

16(17)-EpDPE

Definition

16(17)-EpETE is the DHA homolog of 14(15)-EpETrE, derived via epoxidation of the 16,17-double bond of docosahexaenoic acid (DHA). The EDHF (endothelium-derived hyperpolarizing factor) activity of 16(17)-EpDPE has not yet been determined. The epoxygenase metabolites of DHA have also been detected in a murine inflammation model (PMID: 12391014 ). EDHF is an unidentified mediator released from vascular endothelial cells in response to acetylcholine and bradykinin which is distinct from the NOS- (nitric oxide) and COX-derived (prostacyclin) vasodilators (PMID: 9504399 , 10519554 ). Cytochrome P450 (CYP450) metabolism of polyunsaturated fatty acids produces epoxides such as 14(15)-EpETrE which are prime candidates for the actual active mediator (PMID: 9401962 ). However, the CYP450 metabolites of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) have been little studied relative to arachidonate epoxygenase metabolites.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
16(17)-Epoxy-4Z,7Z,10Z,13Z,19Z-docosapentaenoic acid	ChEBI
16,17-EDP	ChEBI
16,17-Epoxydocosapentaenoic acid	ChEBI
16(17)-Epoxy-4Z,7Z,10Z,13Z,19Z-docosapentaenoate	Generator
16,17-Epoxydocosapentaenoate	Generator
16(17)-EpDoPE	HMDB

Chemical Formula

C₂₂H₃₂O₃

Average Molecular Weight

344.4877

Monoisotopic Molecular Weight

344.23514489

IUPAC Name

(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoic acid

Traditional Name

(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoic acid

CAS Registry Number

None

SMILES

CC\C=C/CC1OC1C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O

InChI Identifier

InChI=1S/C22H32O3/c1-2-3-14-17-20-21(25-20)18-15-12-10-8-6-4-5-7-9-11-13-16-19-22(23)24/h3,5-8,11-15,20-21H,2,4,9-10,16-19H2,1H3,(H,23,24)/b7-5-,8-6-,13-11-,14-3-,15-12-

InChI Key

BCTXZWCPBLWCRV-ZYADFMMDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Epoxy fatty acid
Heterocyclic fatty acid
Unsaturated fatty acid
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

EpDPE (CHEBI:72855 )
Docosanoids (LMFA04000037 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0013621)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0013621)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013621)

Source

Endogenous

Endogenous (HMDB: HMDB0013621)

Animal

Animal (HMDB: HMDB0013621)

Exogenous

Food

Food (HMDB: HMDB0013621)

Exogenous (HMDB: HMDB0013621)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013621)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013621)

Lipid metabolism pathway (HMDB: HMDB0013621)

Cellular process

Cell signaling (HMDB: HMDB0013621)

Biochemical process

Lipid transport (HMDB: HMDB0013621)

Role

Biological role

Energy source (HMDB: HMDB0013621)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013621)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00027 g/L	ALOGPS
logP	6.16	ALOGPS
logP	5.81	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	109.79 m³·mol⁻¹	ChemAxon
Polarizability	40.41 Å³	ChemAxon
Number of Rings	1	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

HMDB0013621

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029598

KNApSAcK ID

Not Available

Chemspider ID

21466945

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14392758

PDB ID

Not Available

ChEBI ID

72855

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 16(17)-EpDPE (CFc000008512)

MOL for CFc000008512 (16(17)-EpDPE)

3D MOL for CFc000008512 (16(17)-EpDPE)

3D SDF for CFc000008512 (16(17)-EpDPE)

3D-SDF for CFc000008512 (16(17)-EpDPE)

PDB for CFc000008512 (16(17)-EpDPE)

3D PDB for CFc000008512 (16(17)-EpDPE)

SMILES for CFc000008512 (16(17)-EpDPE)

INCHI for CFc000008512 (16(17)-EpDPE)

Structure for CFc000008512 (16(17)-EpDPE)

3D Structure for CFc000008512 (16(17)-EpDPE)