ChemFOnt: Showing chemical card for 15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid (CFc000042703)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:21 UTC

Chemfont ID

CFc000042703

Molecule Identification

Common Name

15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid

Definition

15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid is also known as 13,14-dihydro-15-keto-Lipoxin a4 or DHK-LXA4. 15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid is considered to be practically insoluble (in water) and acidic. 15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid is an eicosanoid lipid molecule

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
13,14-Dihydro-15-keto-lipoxin a4	ChEBI
13,14-Dihydro-15-keto-lxa4	ChEBI
15-oxo-5S,6R-Dihydroxy-7E,9E,11Z-eicosatrienoic acid	ChEBI
DHK-LXA4	ChEBI
15-oxo-5S,6R-Dihydroxy-7E,9E,11Z-eicosatrienoate	Generator

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.471

Monoisotopic Molecular Weight

352.22497413

IUPAC Name

(5S,6R,7E,9E,11Z)-5,6-dihydroxy-15-oxoicosa-7,9,11-trienoic acid

Traditional Name

dhk-LXA4

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O5/c1-2-3-8-12-17(21)13-9-6-4-5-7-10-14-18(22)19(23)15-11-16-20(24)25/h4-7,10,14,18-19,22-23H,2-3,8-9,11-13,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,14-10+/t18-,19+/m1/s1

InChI Key

FPRPRBFSKMFXRV-JWVNNVTNSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatrienoic acids

Alternative Parents

Substituents

Hydroxyeicosatrienoic acid
Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Fatty acid
Secondary alcohol
Ketone
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:63993 )
icosanoid (CHEBI:63993 )
oxo fatty acid (CHEBI:63993 )
trienoic fatty acid (CHEBI:63993 )
hydroxy fatty acid (CHEBI:63993 )
Lipoxins (LMFA03040008 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062291)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	3.57	ALOGPS
logP	3.46	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	102.36 m³·mol⁻¹	ChemAxon
Polarizability	41.33 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

HMDB0062291

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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

52921885

PDB ID

Not Available

ChEBI ID

63993

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid (CFc000042703)

MOL for CFc000042703 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid)

3D MOL for CFc000042703 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid)

3D SDF for CFc000042703 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid)

3D-SDF for CFc000042703 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid)

PDB for CFc000042703 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid)

3D PDB for CFc000042703 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid)

SMILES for CFc000042703 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid)

INCHI for CFc000042703 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid)

Structure for CFc000042703 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid)

3D Structure for CFc000042703 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z-eicosatrienoic acid)