ChemFOnt: Showing chemical card for (5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate (CFc000283493)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:49 UTC

Chemfont ID

CFc000283493

Molecule Identification

Common Name

(5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate

Definition

(5z)-(15s)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate, also known as 15-dehydro-prostaglandin e2 anion, is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds 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 (5z)-(15s)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (5z)-(15s)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate can be found in a number of food items such as maitake, green zucchini, yellow pond-lily, and canada blueberry, which makes (5z)-(15s)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
15-Dehydro-prostaglandin e2 anion	ChEBI
15-Oxoprostaglandin e2	ChEBI
15-oxo-Prostaglandin e2	ChEBI
9,15-dioxo-11-Hydroxyprosta-5,13-dienoic acid	MeSH
15-keto-PGE2	MeSH
15-keto-Prostaglandin e2	MeSH
15-Ketoprostaglandin e2	MeSH
15-oxo-PGE2	MeSH
15-Ketoprostaglandin e2, (11alpha)-isomer	MeSH
(5Z)-(15S)-11-Α-hydroxy-9,15-dioxoprosta-13-enoic acid	Generator

Chemical Formula

C₂₀H₂₉O₅

Average Molecular Weight

349.448

Monoisotopic Molecular Weight

349.202047614

IUPAC Name

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

Traditional Name

15-dehydro-prostaglandin E2

CAS Registry Number

Not Available

SMILES

[H]\C(CCCC([O-])=O)=C(/[H])C[C@@]1([H])C(=O)C[C@@]([H])(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/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/p-1/b7-4-,13-12+/t16-,17-,19-/m1/s1

InChI Key

YRTJDWROBKPZNV-KMXMBPPJSA-M

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandin carboxylic acid anion (CHEBI:57400 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.034 g/L	ALOGPS
logP	3.1	ALOGPS
logP	3.64	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.5 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	109.37 m³·mol⁻¹	ChemAxon
Polarizability	38.55 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

HMDB0303977

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030125

KNApSAcK ID

Not Available

Chemspider ID

26330771

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

57400

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate (CFc000283493)

MOL for CFc000283493 ((5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate)

3D MOL for CFc000283493 ((5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate)

3D SDF for CFc000283493 ((5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate)

3D-SDF for CFc000283493 ((5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate)

PDB for CFc000283493 ((5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate)

3D PDB for CFc000283493 ((5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate)

SMILES for CFc000283493 ((5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate)

INCHI for CFc000283493 ((5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate)

Structure for CFc000283493 ((5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate)

3D Structure for CFc000283493 ((5Z)-(15S)-11-alpha-hydroxy-9,15-dioxoprosta-13-enoate)