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Identification
Name(11-BETA)-11,21-DIHYDROXY-PREGN-4-ENE-3,20-DIONE
Accession NumberDB04652
Typesmall molecule
Groupsexperimental
Description

An adrenocortical steroid that has modest but significant activities as a mineralocorticoid and a glucocorticoid. (From Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p1437)

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS numberNot Available
WeightAverage: 346.4605
Monoisotopic: 346.214409448
Chemical FormulaC21H30O4
InChI KeyInChIKey=OMFXVFTZEKFJBZ-HJTSIMOOSA-N
InChI
InChI=1S/C21H30O4/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/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1
IUPAC Name
(1S,2R,10S,11S,14S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@@]([H])(O)C[C@]12C)C(=O)CO
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsHydroxysteroids; Ketosteroids; Cyclohexanols; Ketones; Cyclic Alcohols and Derivatives; Primary Alcohols; Enolates; Polyamines; Aldehydes
Substituents3-keto-steroid; 11-hydroxy-steroid; 20-keto-steroid; cyclohexanol; cyclic alcohol; ketone; secondary alcohol; primary alcohol; enolate; polyamine; alcohol; carbonyl group; aldehyde
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9926
Blood Brain Barrier + 0.9451
Caco-2 permeable + 0.8867
P-glycoprotein substrate Substrate 0.771
P-glycoprotein inhibitor I Non-inhibitor 0.7124
P-glycoprotein inhibitor II Non-inhibitor 0.7259
Renal organic cation transporter Non-inhibitor 0.7122
CYP450 2C9 substrate Non-substrate 0.8363
CYP450 2D6 substrate Non-substrate 0.9143
CYP450 3A4 substrate Substrate 0.7636
CYP450 1A2 substrate Non-inhibitor 0.9255
CYP450 2C9 substrate Non-inhibitor 0.9211
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9593
CYP450 3A4 substrate Non-inhibitor 0.8246
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8716
Ames test Non AMES toxic 0.926
Carcinogenicity Non-carcinogens 0.9497
Biodegradation Not ready biodegradable 0.9454
Rat acute toxicity 1.5110 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9403
hERG inhibition (predictor II) Non-inhibitor 0.5206
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility4.60e-02 g/lALOGPS
logP2.09ALOGPS
logP2.02ChemAxon
logS-3.9ALOGPS
pKa (strongest acidic)13.86ChemAxon
pKa (strongest basic)-0.26ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count4ChemAxon
hydrogen donor count2ChemAxon
polar surface area74.6ChemAxon
rotatable bond count2ChemAxon
refractivity96ChemAxon
polarizability38.79ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound5753
PubChem Substance46504547
ChemSpider5550
HETC0R
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Mineralocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Mineralocorticoid receptor P08235 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

2. Corticosteroid 11-beta-dehydrogenase isozyme 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Corticosteroid 11-beta-dehydrogenase isozyme 1 P28845 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

3. Nuclear receptor coactivator 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Nuclear receptor coactivator 1 Q15788 Details

References:

  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

Comments
Drug created on September 11, 2007 11:49 / Updated on September 16, 2013 17:25