ChemFOnt: Showing chemical card for 15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid (CFc000042712)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:45:22 UTC

Chemfont ID

CFc000042712

Molecule Identification

Common Name

15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid

Definition

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

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5S,6R,7E,9E,11Z)-5,6-Dihydroxy-15-oxoicosa-7,9,11,13-tetraenoate	Generator
15-oxo-5S,6R-Dihydroxy-7E,9E,11Z,13E-eicosatetraenoate	Generator
15-keto-Lipoxin a4	HMDB
15-keto-LXA4	HMDB
15-oxo-LXA4	HMDB

Chemical Formula

C₂₀H₃₀O₅

Average Molecular Weight

350.455

Monoisotopic Molecular Weight

350.209324066

IUPAC Name

(5S,6R,7E,9E,11Z)-5,6-dihydroxy-15-oxoicosa-7,9,11,13-tetraenoic acid

Traditional Name

(5S,6R,7E,9E,11Z)-5,6-dihydroxy-15-oxoicosa-7,9,11,13-tetraenoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O5/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/h4-7,9-10,13-14,18-19,22-23H,2-3,8,11-12,15-16H2,1H3,(H,24,25)/b6-4-,7-5+,13-9?,14-10+/t18-,19+/m1/s1

InChI Key

KMQGFEBCBYXSPZ-LJWKICLNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lipoxins. These are eicosanoids with a trihydroxyicosatetraenoic acid skeleton (a c20-fatty acid, with the chain bearing three hydroxyl groups and four double bonds). Lipoxins have four double bonds, which are all conjugated. In some cases a hydroxyl group is substituted by a C=O group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Lipoxins

Alternative Parents

Substituents

Lipoxin
Long-chain fatty acid
Hydroxy fatty acid
Unsaturated fatty acid
Fatty acid
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
1,2-diol
Secondary alcohol
Ketone
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

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062300)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.03 g/L	ALOGPS
logP	3.58	ALOGPS
logP	3.46	ChemAxon
logS	-4.1	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	14	ChemAxon
Refractivity	103.45 m³·mol⁻¹	ChemAxon
Polarizability	40.67 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

HMDB0062300

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid (CFc000042712)

MOL for CFc000042712 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid)

3D MOL for CFc000042712 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid)

3D SDF for CFc000042712 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid)

3D-SDF for CFc000042712 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid)

PDB for CFc000042712 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid)

3D PDB for CFc000042712 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid)

SMILES for CFc000042712 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid)

INCHI for CFc000042712 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid)

Structure for CFc000042712 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid)

3D Structure for CFc000042712 (15-oxo-5S,6R-dihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid)