ChemFOnt: Showing chemical card for (13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid (CFc000001018)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:33 UTC

Chemfont ID

CFc000001018

Molecule Identification

Common Name

(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid

Definition

(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid is a substrate for Carbonyl reductase 1.Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoate	ChEBI
(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoate	Generator
(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoic acid	Generator
(13E)-11Α-hydroxy-9,15-dioxoprost-13-enoate	Generator
(13E)-11Α-hydroxy-9,15-dioxoprost-13-enoic acid	Generator
(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-en-1-Oic acid	HMDB
(13E)-11a-Hydroxy-9,15-dioxoprost-13-en-1-Oate	HMDB
(13E)-11a-Hydroxy-9,15-dioxoprost-13-en-1-Oic acid	HMDB
(13E)-11alpha-Hydroxy-9,15-dioxoprost-13-en-1-Oate	HMDB
(13E)-11Α-hydroxy-9,15-dioxoprost-13-en-1-Oate	HMDB
(13E)-11Α-hydroxy-9,15-dioxoprost-13-en-1-Oic acid	HMDB
(11a,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-Oate	HMDB
(11a,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-Oic acid	HMDB
(11alpha,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-Oate	HMDB
(11alpha,13E)-11-Hydroxy-9,15-dioxoprost-13-en-1-Oic acid	HMDB
(13E)-11-alpha-Hydroxy-9,15-dioxoprost-13-enoate	HMDB
(13E)-11-alpha-Hydroxy-9,15-dioxoprost-13-enoic acid	HMDB
1-Hydroxy-9,15-dioxo-(11a,13E)-prost-13-en-1-Oate	HMDB
1-Hydroxy-9,15-dioxo-(11a,13E)-prost-13-en-1-Oic acid	HMDB
15-Keto pge1	HMDB
15-Keto-pge	HMDB
15-Keto-pge1	HMDB
15-Keto-pge1-alpha	HMDB
15-Keto-prostaglandin e1	HMDB
15-Ketoprostaglandin e	HMDB
15-Ketoprostaglandin e1	HMDB
15-oxo-PGE1	HMDB
15-Oxoprostaglandin e1	HMDB
3-Hydroxy-5-oxo-2-(3-oxo-1-octenyl)-cyclopentaneheptanoate	HMDB
3-Hydroxy-5-oxo-2-(3-oxo-1-octenyl)-cyclopentaneheptanoic acid	HMDB
9,15-Dioxo-11R-hydroxy-13E-prostaenoate	HMDB
9,15-Dioxo-11R-hydroxy-13E-prostaenoic acid	HMDB
15-Ketoprostaglandin e, (11alpha,13E)-(+-)-isomer	HMDB
15-Ketoprostaglandin e, (5Z,11alpha)-isomer, 2H-labeled	HMDB
(13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acid	Generator

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

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

Traditional Name

15-keto-PGE1

CAS Registry Number

22973-19-9

SMILES

CCCCCC(=O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O

InChI Identifier

InChI=1S/C20H32O5/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/h12-13,16-17,19,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t16-,17-,19-/m1/s1

InChI Key

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandins E (CHEBI:15548 )
Prostaglandins (LMFA03010146 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001320)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001320)

Source

Endogenous

Endogenous (HMDB: HMDB0001320)

Animal

Animal (HMDB: HMDB0001320)

Exogenous

Food

Food (HMDB: HMDB0001320)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0001320)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0001320)

Modulator

Immunomodulator (HMDB: HMDB0001320)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001320)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.051 g/L	ALOGPS
logP	3.37	ALOGPS
logP	4	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.35	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	13	ChemAxon
Refractivity	97.42 m³·mol⁻¹	ChemAxon
Polarizability	40.82 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