5beta-dihydrotestosterone

Identification

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Name
5beta-dihydrotestosterone
Accession Number
DB07447
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
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
Categories
UNII
Not Available
CAS number
571-22-2
Weight
Average: 290.4403
Monoisotopic: 290.224580204
Chemical Formula
C19H30O2
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,2S,7R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
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
(R)-warfarin5beta-dihydrotestosterone may increase the anticoagulant activities of (R)-warfarin.
(S)-Warfarin5beta-dihydrotestosterone may increase the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarin5beta-dihydrotestosterone may increase the anticoagulant activities of 4-hydroxycoumarin.
Abciximab5beta-dihydrotestosterone may increase the anticoagulant activities of Abciximab.
Acenocoumarol5beta-dihydrotestosterone may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acid5beta-dihydrotestosterone may increase the anticoagulant activities of Acetylsalicylic acid.
Alteplase5beta-dihydrotestosterone may increase the anticoagulant activities of Alteplase.
Amediplase5beta-dihydrotestosterone may increase the anticoagulant activities of Amediplase.
Anagrelide5beta-dihydrotestosterone may increase the anticoagulant activities of Anagrelide.
Ancrod5beta-dihydrotestosterone may increase the anticoagulant activities of Ancrod.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

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

Clinical Trials

Clinical Trials
Not Available

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
Polarizability34.46 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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Androgen-skeleton / 3-oxosteroid / 3-oxo-5-beta-steroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Cyclic alcohol / Cyclic ketone / Secondary alcohol / Ketone
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)

Targets

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. [PubMed:10592235]

Drug created on September 15, 2010 15:21 / Updated on November 02, 2019 02:10