ChemFOnt: Showing chemical card for 11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid (CFc000007231)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:53:27 UTC

Chemfont ID

CFc000007231

Molecule Identification

Common Name

11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid

Definition

11b,20-dihydroxy-3-oxopregn-4-en-21-oic acid or DHOPA is a major metabolite of corticosterone that is typically elevated in the liver. The in vivo conversion of corticosterone to DHOPA is thought to proceed via the aldehyde intermediate 11b-hydroxy-3,20-dioxopregn-4-en-21-al. Cytochrome P450 3A4 (CYP3A4), is known to convert corticosterone to the gem-diol form of the aldehyde. Because CYP3A4 is highly abundant in the liver, the conversion of corticosterone to its aldehyde presumably occurs readily, and the formation of DHOPA by isomerization of the aldehyde. DHOPA has also been identified as a biomarker that is elevated (50 X) in animals that have been treated with PPARalpha agonists. Peroxisome proliferator-activated receptor alpha (PPARalpha) is a nuclear receptor with manifold effects on intermediary metabolism (PMID: 17550978 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
11b,20-Dihydroxy-3-oxopregn-4-en-21-Oate	Generator
11b,20-Dihydroxy-3-oxopregn-4-en-21-Oic acid	Generator
11beta,20-Dihydroxy-3-oxopregn-4-en-21-Oate	Generator
11Β,20-dihydroxy-3-oxopregn-4-en-21-Oate	Generator
11Β,20-dihydroxy-3-oxopregn-4-en-21-Oic acid	Generator
DHOPA	HMDB
3-[(2R,15S,17S)-17-Hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-3-oxopropanoate	Generator

Chemical Formula

C₂₂H₃₀O₅

Average Molecular Weight

374.4706

Monoisotopic Molecular Weight

374.20932407

IUPAC Name

3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-3-oxopropanoic acid

Traditional Name

3-[(2R,15S,17S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-3-oxopropanoic acid

CAS Registry Number

None

SMILES

C[C@]12C[C@H](O)C3C(CCC4=CC(=O)CC[C@]34C)C1CCC2C(=O)CC(O)=O

InChI Identifier

InChI=1S/C22H30O5/c1-21-8-7-13(23)9-12(21)3-4-14-15-5-6-16(17(24)10-19(26)27)22(15,2)11-18(25)20(14)21/h9,14-16,18,20,25H,3-8,10-11H2,1-2H3,(H,26,27)/t14?,15?,16?,18-,20?,21-,22-/m0/s1

InChI Key

VUDYWBBYQWVFAG-GKLBWGGBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

20-oxosteroids

Alternative Parents

Substituents

20-oxosteroid
Androgen-skeleton
Steroid acid
Androstane-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Beta-keto acid
1,3-dicarbonyl compound
Beta-hydroxy ketone
Keto acid
Cyclic alcohol
Secondary alcohol
Cyclic ketone
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0011651)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0011651)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0011651)

Source

Endogenous

Endogenous (HMDB: HMDB0011651)

Animal

Animal (HMDB: HMDB0011651)

Exogenous

Food

Food (HMDB: HMDB0011651)

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: HMDB0011651)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0011651)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0011651)

Lipid metabolism pathway (HMDB: HMDB0011651)

Cellular process

Cell signaling (HMDB: HMDB0011651)

Biochemical process

Lipid transport (HMDB: HMDB0011651)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0011651)

Molecular messenger

Signaling molecule (HMDB: HMDB0011651)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0011651)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	2.28	ALOGPS
logP	2.73	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.21	ChemAxon
pKa (Strongest Basic)	-0.26	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	3	ChemAxon
Refractivity	100.64 m³·mol⁻¹	ChemAxon
Polarizability	41.03 Å³	ChemAxon
Number of Rings	4	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

HMDB0011651

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028342

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

53481011

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid (CFc000007231)

MOL for CFc000007231 (11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid)

3D MOL for CFc000007231 (11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid)

3D SDF for CFc000007231 (11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid)

3D-SDF for CFc000007231 (11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid)

PDB for CFc000007231 (11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid)

3D PDB for CFc000007231 (11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid)

SMILES for CFc000007231 (11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid)

INCHI for CFc000007231 (11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid)

Structure for CFc000007231 (11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid)

3D Structure for CFc000007231 (11beta,20-Dihydroxy-3-oxopregn-4-en-21-oic acid)