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Identification
NameDelta1-dihydrotestosterone
Accession NumberDB01481
TypeSmall Molecule
GroupsExperimental, Illicit
Description

Delta1-dihydrotestosterone is an anabolic steroid that differs from testosterone by having a 1,2-double bond instead of 4,5-double bond in its A ring. [Wikipedia]

Structure
Thumb
Synonyms
1-T
1-Testo
1-testosterone
17beta-hydroxy-5alpha-androst-1-en-3-one
External Identifiers 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
SaltsNot Available
CategoriesNot Available
UNIIY984BV1Q0G
CAS number65-06-5
WeightAverage: 288.4244
Monoisotopic: 288.20893014
Chemical FormulaC19H28O2
InChI KeyInChIKey=OKJCFMUGMSVJBG-ABEVXSGRSA-N
InChI
InChI=1S/C19H28O2/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/h7,9,12,14-17,21H,3-6,8,10-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
IUPAC Name
(1S,2R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one
SMILES
[H][C@@]12CC[[email protected]](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)C=C[C@]12C
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-oxo-5-alpha-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-1-steroid
  • Delta-1-steroid
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsDelta1-dihydrotestosterone binds to the androgen receptor, a nuclear receptor which binds the androgenic hormones testosterone and dihydrotestosterone. Once bound, the receptor/ligand complex localizes to the nucleus and acts as a DNA binding transcription factor, regulating gene expression. In animals, Delta1-dihydrotestosterone stimulates the growth of the prostate as well as the seminal vesicles.
Mechanism of actionDelta1-dihydrotestosterone binds to the androgen receptor, a nuclear receptor which binds the androgenic hormones testosterone and dihydrotestosterone. Once bound, the receptor/ligand complex localizes to the nucleus and acts as a DNA binding transcription factor, regulating gene expression.
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 organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9835
Caco-2 permeable+0.8943
P-glycoprotein substrateSubstrate0.6036
P-glycoprotein inhibitor INon-inhibitor0.5133
P-glycoprotein inhibitor IINon-inhibitor0.8114
Renal organic cation transporterNon-inhibitor0.791
CYP450 2C9 substrateNon-substrate0.7459
CYP450 2D6 substrateNon-substrate0.9292
CYP450 3A4 substrateSubstrate0.7431
CYP450 1A2 substrateNon-inhibitor0.7338
CYP450 2C9 inhibitorNon-inhibitor0.9397
CYP450 2D6 inhibitorNon-inhibitor0.9672
CYP450 2C19 inhibitorNon-inhibitor0.8086
CYP450 3A4 inhibitorNon-inhibitor0.8474
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.933
Ames testNon AMES toxic0.9268
CarcinogenicityNon-carcinogens0.9287
BiodegradationNot ready biodegradable0.983
Rat acute toxicity2.0714 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9314
hERG inhibition (predictor II)Non-inhibitor0.6661
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0128 mg/mLALOGPS
logP3.38ALOGPS
logP3.41ChemAxon
logS-4.3ALOGPS
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
Refractivity84.7 m3·mol-1ChemAxon
Polarizability34.06 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  1. Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schanzer W, Thevis M, Vollmer G, Zierau O, Diel P: 17beta-hydroxy-5alpha-androst-1-en-3-one (1-testosterone) is a potent androgen with anabolic properties. Toxicol Lett. 2006 Aug 20;165(2):149-55. Epub 2006 Apr 18. [PubMed:16621347 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  3. Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schanzer W, Thevis M, Vollmer G, Zierau O, Diel P: 17beta-hydroxy-5alpha-androst-1-en-3-one (1-testosterone) is a potent androgen with anabolic properties. Toxicol Lett. 2006 Aug 20;165(2):149-55. Epub 2006 Apr 18. [PubMed:16621347 ]
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Drug created on July 31, 2007 07:09 / Updated on September 16, 2013 17:14