NAV

5alpha-androstane-3beta,17alpha-diol

Identification

Generic Name
5alpha-androstane-3beta,17alpha-diol
DrugBank Accession Number
DB03926
Background

5alpha-androstane-3beta,17alpha-diol is the unspecified form of the steroid, normally a major metabolite of testosterone with androgenic activity. It has been implicated as a regulator of gonadotropin secretion.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 292.4562
Monoisotopic: 292.240230268
Chemical Formula
C19H32O2
Synonyms
  • 3beta,17alpha-Dihydroxy-5alpha-androstane
  • 5alpha-Androstan-3beta,17alpha-diol
  • 5α-androstane-3β,17α-diol
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-beta-hydroxysteroids / 17-hydroxysteroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / 3-beta-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Cyclic alcohol / Hydrocarbon derivative / Hydroxysteroid / Organic oxygen compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3beta-hydroxy steroid, 17alpha-hydroxy steroid, androstane-3,17-diol (CHEBI:40836) / C19 steroids (androgens) and derivatives (LMST02020080)
Affected organisms
Not Available

Chemical Identifiers

UNII
0IF82ZEY2K
CAS number
5856-11-1
InChI Key
CBMYJHIOYJEBSB-MFXFBURESA-N
InChI
InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17+,18-,19-/m0/s1
IUPAC Name
(1R,3aS,3bR,5aS,7S,9aS,9bS,11aS)-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthrene-1,7-diol
SMILES
[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C

References

General References
Not Available
PubChem Compound
446934
PubChem Substance
46505400
ChemSpider
394165
ChEBI
40836
ZINC
ZINC000006500050
PDBe Ligand
AON
PDB Entries
1lhn

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0193 mg/mLALOGPS
logP3.56ALOGPS
logP3.2Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.3Chemaxon
pKa (Strongest Basic)-0.76Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity84.63 m3·mol-1Chemaxon
Polarizability35.45 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9594
Caco-2 permeable+0.8756
P-glycoprotein substrateSubstrate0.6149
P-glycoprotein inhibitor INon-inhibitor0.768
P-glycoprotein inhibitor IINon-inhibitor0.8804
Renal organic cation transporterNon-inhibitor0.8018
CYP450 2C9 substrateNon-substrate0.7997
CYP450 2D6 substrateNon-substrate0.891
CYP450 3A4 substrateSubstrate0.7189
CYP450 1A2 substrateInhibitor0.7258
CYP450 2C9 inhibitorNon-inhibitor0.9164
CYP450 2D6 inhibitorNon-inhibitor0.9658
CYP450 2C19 inhibitorNon-inhibitor0.9117
CYP450 3A4 inhibitorNon-inhibitor0.8729
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9084
Ames testNon AMES toxic0.9176
CarcinogenicityNon-carcinogens0.8999
BiodegradationNot ready biodegradable0.9858
Rat acute toxicity2.3334 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9223
hERG inhibition (predictor II)Inhibitor0.5
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002f-0090000000-65fc42e86d9de94cc4c4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-58f961d0737c2e2d3336
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-cc08d0cda75cca67b15c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-4930000000-6ffa83c23a4f4375d50b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-0090000000-6183e653a184071476a0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-6e21973b5afece47877a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-177.9662958
predicted
DarkChem Lite v0.1.0
[M-H]-173.41946
predicted
DeepCCS 1.0 (2019)
[M+H]+175.0432958
predicted
DarkChem Lite v0.1.0
[M+H]+175.3149
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.0802958
predicted
DarkChem Lite v0.1.0
[M+Na]+181.09282
predicted
DeepCCS 1.0 (2019)

Carriers

Details1. Sex hormone-binding globulin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52