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
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIIW980KJ009P
CAS numberNot Available
WeightAverage: 346.4605
Monoisotopic: 346.214409448
Chemical FormulaC21H30O4
InChI KeyOMFXVFTZEKFJBZ-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[8.7.0.0²,⁷.0¹¹,¹⁵]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
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Mineralocorticoid receptorProteinunknownNot AvailableHumanP08235 details
Corticosteroid 11-beta-dehydrogenase isozyme 1ProteinunknownNot AvailableHumanP28845 details
Nuclear receptor coactivator 1ProteinunknownNot AvailableHumanQ15788 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
17-alpha-hydroxylase deficiency (CYP17)DiseaseSMP00566
Corticosterone methyl oxidase I deficiency (CMO I)DiseaseSMP00577
SteroidogenesisMetabolicSMP00130
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase DeficiencyDiseaseSMP00373
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHDiseaseSMP00371
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase DeficiencyDiseaseSMP00372
11-beta-hydroxylase deficiency (CYP11B1)DiseaseSMP00575
Corticosterone methyl oxidase II deficiency - CMO IIDiseaseSMP00578
21-hydroxylase deficiency (CYP21)DiseaseSMP00576
Apparent mineralocorticoid excess syndromeDiseaseSMP00717
3-Beta-Hydroxysteroid Dehydrogenase DeficiencyDiseaseSMP00718
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.046 mg/mLALOGPS
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 Area74.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity96 m3·mol-1ChemAxon
Polarizability38.79 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9926
Blood Brain Barrier+0.9451
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.771
P-glycoprotein inhibitor INon-inhibitor0.7124
P-glycoprotein inhibitor IINon-inhibitor0.7259
Renal organic cation transporterNon-inhibitor0.7122
CYP450 2C9 substrateNon-substrate0.8363
CYP450 2D6 substrateNon-substrate0.9143
CYP450 3A4 substrateSubstrate0.7636
CYP450 1A2 substrateNon-inhibitor0.9255
CYP450 2C9 inhibitorNon-inhibitor0.9211
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9593
CYP450 3A4 inhibitorNon-inhibitor0.8246
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8716
Ames testNon AMES toxic0.926
CarcinogenicityNon-carcinogens0.9497
BiodegradationNot ready biodegradable0.9454
Rat acute toxicity1.5110 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9403
hERG inhibition (predictor II)Non-inhibitor0.5206
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 2 TMS)splash10-0f9l-4920000000-13c56138ef34befd6786View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 MEOX; 2 TMS)splash10-0f7c-4921100000-1d2ace868fd94080c88eView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-014i-1798000000-b39fe3c8aaf8f09d7cdeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0009000000-81d0a5e41401c962645eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05fs-2910000000-7a585bd042169de23cfeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0597-6900000000-4c9bb40342921d7ff55eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-014i-1798000000-e8ef26b439701fc96537View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0009000000-362accabc0136898e549View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0459000000-e31660ef75e29d9d9d78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00fr-0941000000-1453953f7526fa9b8de6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00e9-0920000000-da03f39d4590a6248157View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00gi-0900000000-2ec9e62e392a282f6de4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0009000000-1db6d72ffc02b6efa63dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00ba-1964000000-d35661aaf929a1609854View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00dj-2920000000-b29d21507e63bc379164View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05fv-3900000000-8cd56447e4fa2da8c30bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0596-4900000000-0fdf5a6f27425f6540baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-052f-6900000000-d6cd49302b0991f7a681View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00mo-9800000000-fcf363e8a5a69914ad88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00mp-9600000000-493d479336ae32a15124View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-016u-9500000000-5e6760693c17aadb3f80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0169000000-f22e1aba4ac6510b7c67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0759000000-8c04fadb6bd7d3e86c28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05gi-3920000000-db0dc9413f5ca5cb69e3View in MoNA
MSMass Spectrum (Electron Ionization)splash10-014i-8953000000-cdd7d53a6012a6eb3f28View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative ParentsGluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 3-oxo delta-4-steroids / 11-beta-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Alpha-hydroxy ketones / Secondary alcohols / Cyclic alcohols and derivatives / Primary alcohols
SubstituentsProgestogin-skeleton / 21-hydroxysteroid / Pregnane-skeleton / 20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / 11-hydroxysteroid / 11-beta-hydroxysteroid / Oxosteroid / Delta-4-steroid
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors3-oxo steroid, 11beta-hydroxy steroid, glucocorticoid, 20-oxo steroid, 21-hydroxy steroid, C21-steroid (CHEBI:16827 ) / Pregnane and derivatives [Fig], C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives, Mineralocorticoids (C02140 ) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030186 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates target genes. The effect of MC is to increase ion and water transport and thus raise extracellular fluid volume and blood pressure and lower potassium levels.
Gene Name:
NR3C2
Uniprot ID:
P08235
Molecular Weight:
107066.575 Da
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:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
11-beta-hydroxysteroid dehydrogenase [nad(p)] activity
Specific Function:
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
Gene Name:
HSD11B1
Uniprot ID:
P28845
Molecular Weight:
32400.665 Da
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:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Transcription coactivator activity
Specific Function:
Nuclear receptor coactivator that directly binds nuclear receptors and stimulates the transcriptional activities in a hormone-dependent fashion. Involved in the coactivation of different nuclear receptors, such as for steroids (PGR, GR and ER), retinoids (RXRs), thyroid hormone (TRs) and prostanoids (PPARs). Also involved in coactivation mediated by STAT3, STAT5A, STAT5B and STAT6 transcription...
Gene Name:
NCOA1
Uniprot ID:
Q15788
Molecular Weight:
156755.44 Da
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:10592235 ]
Drug created on September 11, 2007 11:49 / Updated on June 11, 2017 16:36