Showing Compound 11-Dehydrocorticosterone (FDB023282)

Record Information

Version

1.0

Creation date

2011-09-21 00:27:26 UTC

Update date

2015-07-21 06:57:37 UTC

Primary ID

FDB023282

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

11-Dehydrocorticosterone

Description

11-Dehydrocorticosterone is a mineral corticosteroid. The conversion of inactive 11-ketoglucocorticoids such as 11-dehydrocorticosterone) into active 11b-hydroxyglucocorticoids (such as corticosterone) is catalyzed by 11beta-hydroxysteroid dehydrogenase (11b-HSD1, EC 1.1.1.146), which is expressed in many tissues and plays an important role in metabolically relevant tissues such as the liver, adipose tissue, skeletal muscles and possibly kidney. Chronically elevated local glucocorticoid action as a result of increased 11beta-HSD1 activity rather than elevated systemic glucocorticoid levels has been associated with metabolic syndrome, which is characterized by obesity, insulin resistance, type 2 diabetes and cardiovascular complications. Recent studies indicate that compounds inhibiting 11beta-HSD1 activity ameliorate the adverse effects of excessive glucocorticoid concentrations on metabolic processes, providing promising opportunities for the development of therapeutic interventions. 11-dehydrocorticosterone and corticosterone display antinatriuretic activity, although 11-dehydrocorticosterone is generally a more potent sodium retainer than corticosterone. (PMID: 17584152, Endocr Metab Immune Disord Drug Targets. 2007 Jun;7(2):125-40.) [HMDB]

CAS Number

72-23-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
11-Dehydro-corticosterone	HMDB
11-dehydro-Corticosterone	hmdb
11-Dehydrocorticosteron	HMDB
11-Dehydrocorticosterone	hmdb
11-Dehydrocorticosterone, 4-(14)C labeled	HMDB
11-oxo-11-Deoxycorticosterone	HMDB
11-Oxo-11-deoxycorticosterone	hmdb
11-Oxocorticosterone	HMDB
17-(1-Keto-2-hydroxyethyl)-D4-androsten-3,11-dione	HMDB
17-(1-keto-2-Hydroxyethyl)-D4-androsten-3,11-dione	hmdb

Showing 1 to 10 of 20 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.048 g/L	ALOGPS
logP	2.44	ALOGPS
logP	2.41	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.07 m³·mol⁻¹	ChemAxon
Polarizability	37.88 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

Chemical Formula

C21H28O4

IUPAC name

(1S,2R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione

InChI Identifier

InChI=1S/C21H28O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-16,19,22H,3-8,10-11H2,1-2H3/t14-,15-,16?,19+,20-,21-/m0/s1

InChI Key

FUFLCEKSBBHCMO-IWBQTIMDSA-N

Isomeric SMILES

[H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Average Molecular Weight

344.4446

Monoisotopic Molecular Weight

344.198759384

Classification

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
11-oxosteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Cyclic ketone
Ketone
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030192 )

Ontology

Kidney cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Organ and components:

Tissue and substructures:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Industrial application:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	11-Dehydrocorticosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ay0-2957000000-6fc60a97523bfe760310	Spectrum
Predicted GC-MS	11-Dehydrocorticosterone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0w99-2659500000-a5e26ad4a729c9a867d2	Spectrum
Predicted GC-MS	11-Dehydrocorticosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	11-Dehydrocorticosterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0019000000-d48d3281c7605fd415d6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056s-0339000000-f07a3d76700b80e9485d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0api-4492000000-80b6e037fc1d1086338b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-f015e4b72a589e24a7e8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08ic-2029000000-f97310fcb21967516849	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ap0-3092000000-ddd908beb917ff18d4ba	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-0009000000-943372b86ff9e56ce09d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03el-0098000000-90a6dc3c6a8170909d50	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0296-1193000000-7d8449abca862335c651	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0029000000-f4e5c8056552eb42bc35	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0550-0294000000-33002f06eeb92b214f1f	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-4890000000-85148d9abab856e92013	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

24850107

ChEMBL ID

Not Available

KEGG Compound ID

C05490

Pubchem Compound ID

13783449

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04029

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB