NAV

5beta-dihydrotestosterone

Identification

Generic Name
5beta-dihydrotestosterone
DrugBank Accession Number
DB07447
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 290.4403
Monoisotopic: 290.224580204
Chemical Formula
C19H30O2
Synonyms
  • (5β,17β)-17-hydroxyandrostan-3-one
  • (5β,8α,17β)-17-hydroxyandrostan-3-one
  • 17β-hydroxyetiocholan-3-one
  • 5-beta-DHT
  • 5β-androstan-17β-ol-3-one
  • 5β-dihydrotestosterone
  • 5β,17β-hydroxyandrostan-3-one
  • etiocholan-17-beta-ol-3-one
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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
TargetActionsOrganism
U3-oxo-5-beta-steroid 4-dehydrogenaseNot AvailableHumans
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
PathwayCategory
17-beta Hydroxysteroid Dehydrogenase III DeficiencyDisease
Androgen and Estrogen MetabolismMetabolic
Aromatase DeficiencyDisease
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.
DrugInteraction
Integrate drug-drug
interactions in your software
Abciximab5beta-dihydrotestosterone may increase the anticoagulant activities of Abciximab.
Acenocoumarol5beta-dihydrotestosterone may increase the anticoagulant activities of Acenocoumarol.
Alteplase5beta-dihydrotestosterone may increase the anticoagulant activities of Alteplase.
Ancrod5beta-dihydrotestosterone may increase the anticoagulant activities of Ancrod.
Anistreplase5beta-dihydrotestosterone may increase the anticoagulant activities of Anistreplase.
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-oxo-5-beta-steroids / 17-hydroxysteroids / Secondary alcohols / Cyclic ketones / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / 3-oxo-5-beta-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Carbonyl group / Cyclic alcohol / Cyclic ketone / Hydrocarbon derivative
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-hydroxy steroid, 17beta-hydroxyandrostan-3-one (CHEBI:2150) / C19 steroids (androgens) and derivatives (C05293) / C19 steroids (androgens) and derivatives (LMST02020069)
Affected organisms
Not Available

Chemical Identifiers

UNII
SVX1G0C5VD
CAS number
571-22-2
InChI Key
NVKAWKQGWWIWPM-MISPCMORSA-N
InChI
InChI=1S/C19H30O2/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/h12,14-17,21H,3-11H2,1-2H3/t12-,14+,15+,16+,17+,18+,19+/m1/s1
IUPAC Name
(1S,3aS,3bR,5aR,9aS,9bS,11aS)-1-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

References

General References
Not Available
Human Metabolome Database
HMDB0006770
KEGG Compound
C05293
PubChem Compound
11302
PubChem Substance
99443918
ChemSpider
10827
BindingDB
50410540
ChEBI
2150
ChEMBL
CHEMBL373357
ZINC
ZINC000003814418
PDBe Ligand
BDT
PDB Entries
3dop / 3uzy

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 Solubility0.00998 mg/mLALOGPS
logP3.37ALOGPS
logP3.41Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19.38Chemaxon
pKa (Strongest Basic)-0.88Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity83.6 m3·mol-1Chemaxon
Polarizability34.62 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9818
Caco-2 permeable+0.8846
P-glycoprotein substrateSubstrate0.57
P-glycoprotein inhibitor INon-inhibitor0.5631
P-glycoprotein inhibitor IINon-inhibitor0.846
Renal organic cation transporterNon-inhibitor0.7884
CYP450 2C9 substrateNon-substrate0.7715
CYP450 2D6 substrateNon-substrate0.93
CYP450 3A4 substrateSubstrate0.7314
CYP450 1A2 substrateNon-inhibitor0.6853
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.971
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8546
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9647
Ames testNon AMES toxic0.9414
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9686
Rat acute toxicity1.9757 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9444
hERG inhibition (predictor II)Non-inhibitor0.576
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03gj-0390000000-9eeab8ff981af1be878c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-0090000000-40d733d9ba1759623bda
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-a795513fa4f735cb43e0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0axr-1950000000-4ab9164a94284c5f2434
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-9f179f519d35e457f736
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-1715fadea1c002681f51
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-c80f645eeb2a77fca2da
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]-177.1639681
predicted
DarkChem Lite v0.1.0
[M-H]-177.2387681
predicted
DarkChem Lite v0.1.0
[M-H]-176.91835
predicted
DeepCCS 1.0 (2019)
[M+H]+178.4668681
predicted
DarkChem Lite v0.1.0
[M+H]+178.4136681
predicted
DarkChem Lite v0.1.0
[M+H]+178.81377
predicted
DeepCCS 1.0 (2019)
[M+Na]+177.1210681
predicted
DarkChem Lite v0.1.0
[M+Na]+177.4351681
predicted
DarkChem Lite v0.1.0
[M+Na]+184.9243
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 3-oxo-5-beta-steroid 4-dehydrogenase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid binding
Specific Function
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihyd...
Gene Name
AKR1D1
Uniprot ID
P51857
Uniprot Name
3-oxo-5-beta-steroid 4-dehydrogenase
Molecular Weight
37376.615 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. [Article]

Drug created at September 15, 2010 21:21 / Updated at June 12, 2020 16:52