ChemFOnt: Showing chemical card for 9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid (CFc000042709)

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

CFc000042709

Molecule Identification

Common Name

9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid

Definition

9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid is also known as 15-Deoxy-15-oxo-prostaglandin D2. 9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid is considered to be practically insoluble (in water) and acidic. 9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid is an eicosanoid lipid molecule

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(5Z,13E)-9alpha-Hydroxy-11,15-dioxoprosta-5,13-dienoate	ChEBI
15-Deoxy-15-oxo-prostaglandin D2	ChEBI
(5Z,13E)-9a-Hydroxy-11,15-dioxoprosta-5,13-dienoate	Generator
(5Z,13E)-9a-Hydroxy-11,15-dioxoprosta-5,13-dienoic acid	Generator
(5Z,13E)-9alpha-Hydroxy-11,15-dioxoprosta-5,13-dienoic acid	Generator
(5Z,13E)-9Α-hydroxy-11,15-dioxoprosta-5,13-dienoate	Generator
(5Z,13E)-9Α-hydroxy-11,15-dioxoprosta-5,13-dienoic acid	Generator
15-dehydro-Prostaglandin D2	KEGG
9S-Hydroxy-11,15-dioxo-5Z,13E-prostadienoate	Generator

Chemical Formula

C₂₀H₃₀O₅

Average Molecular Weight

350.455

Monoisotopic Molecular Weight

350.209324066

IUPAC Name

(5Z)-7-[(1R,2R,5S)-5-hydroxy-3-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

Traditional Name

15-dehydro-prostaglandin D2

CAS Registry Number

Not Available

SMILES

[H]\C(CCCC(O)=O)=C(/[H])C[C@@]1([H])[C@@]([H])(O)CC(=O)[C@]1([H])C([H])=C([H])C(=O)CCCCC

InChI Identifier

InChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-18,22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17-,18+/m1/s1

InChI Key

XEQAHADLFLAPQL-RBIQQSKKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Hydroxy fatty acid
Cyclopentanol
Unsaturated fatty acid
Fatty acid
Alpha,beta-unsaturated ketone
Cyclic alcohol
Acryloyl-group
Enone
Secondary alcohol
Cyclic ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandins D (CHEBI:15557 )
Prostaglandins (LMFA03010206 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0062297)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.057 g/L	ALOGPS
logP	3.27	ALOGPS
logP	3.64	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.4	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	98.54 m³·mol⁻¹	ChemAxon
Polarizability	40.05 Å³	ChemAxon
Number of Rings	1	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

HMDB0062297

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

C04758

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280727

PDB ID

Not Available

ChEBI ID

15557

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid (CFc000042709)

MOL for CFc000042709 (9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid)

3D MOL for CFc000042709 (9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid)

3D SDF for CFc000042709 (9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid)

3D-SDF for CFc000042709 (9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid)

PDB for CFc000042709 (9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid)

3D PDB for CFc000042709 (9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid)

SMILES for CFc000042709 (9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid)

INCHI for CFc000042709 (9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid)

Structure for CFc000042709 (9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid)

3D Structure for CFc000042709 (9S-hydroxy-11,15-dioxo-5Z,13E-prostadienoic acid)