Dihydrotestosterone

Details

• Internal ID: 8522a8e9-c912-4a61-8c0b-7a9d57981d78
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Androstane steroids > Androgens and derivatives
• IUPAC Name: (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• 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-/m0/s1
• InChI Key: NVKAWKQGWWIWPM-ABEVXSGRSA-N
• Popularity: 11,447 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₀O₂
• Molecular Weight: 290.40 g/mol
• Exact Mass: 290.224580195 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.96
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• Androstanolone
• dihydrotestosterone
• 521-18-6
• Andractim
• Anabolex
• Androlone
• Neodrol
• 4-Dihydrotestosterone
• 5alpha-Dihydrotestosterone
• Anaboleen
• Proteina
• Stanaprol
• Protona
• Cristerona MB
• 17beta-Hydroxy-5alpha-androstan-3-one
• DHT
• Androstanolona
• Androstanolonum
• 5alpha-Androstan-17beta-ol-3-one
• 5-alpha-Dihydrotestosterone
• Testosterone, dihydro-
• 4,5alpha-Dihydrotestosterone
• Stanorone
• Dihydrotestosteron
• 17beta-Hydroxyandrostan-3-one
• 5alpha-DHT
• 17beta-Hydroxy-3-androstanone
• dihydrotestosterone (dht)
• NSC 10972
• 5alpha,17beta-Hydroxyandrostan-3-one
• Androstanolone [INN]
• CHEBI:16330
• 17-beta-Hydroxy-5-alpha-androstan-3-one
• 5alpha-dihydrotesosterone
• 5alpha dihydrotestosterone
• NSC-10972
• Androstan-3-one, 17-hydroxy-, (5alpha,17beta)-
• 5.alpha.-Dihydrotestosterone
• 5alpha-Androstan-3-one, 17beta-hydroxy-
• CHEMBL27769
• 4,5.alpha.-Dihydrotestosterone
• 17beta-Hydroxy-androstan-3-one
• 5-alpha-Androstan-3-one, 17-beta-hydroxy-
• DTXSID9022364
• 521-18-6 (free)
• 17.beta.-Hydroxy-3-androstanone
• 08J2K08A3Y
• (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• Androstanolone (INN)
• 17beta-Hydroxy-5alpha-androstane-3-one
• 5.alpha.-Androstan-17.beta.-ol-3-one
• NCGC00091013-01
• Stanolon
• 5.alpha.,17.beta.-Hydroxyandrostan-3-one
• (5alpha,17beta)-17-hydroxyandrostan-3-one
• [3H]DHT
• DTXCID202364
• 5alpha-Dihydroxytestosterone
• Androstan-17beta-ol-3-one
• Androstanolonum [INN-Latin]
• (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one
• CAS-521-18-6
• Androstanolona [INN-Spanish]
• 4,5-alpha-Dihydrotestosterone
• 5-.alpha.-Androstanolone
• 5.alpha.-Androstan-3-one, 17.beta.-hydroxy-
• 17-Hydroxyandrostan-3-one
• [3H]dihydrotestosterone
• [3H]-dihydrotestosterone
• EINECS 208-307-3
• 5alpha,17eta-Hydroxyandrostan-3-one
• Androstan-17.beta.-ol-3-one
• 5-alpha-Androstan-17-beta-ol-3-one
• 17-beta-hydroxyandrostan-3-one
• Androstan-3-one, 17-hydroxy-, (5.alpha.,17.beta.)-
• Andrin
• UNII-08J2K08A3Y
• (+)-Androstan-17.beta.-ol-3-one
• 1kdk
• 2ama
• Androstan-3-one, 17-hydroxy-, (5a,17b)-
• (5-alpha,17-beta)-17-Hydroxyandrostan-3-one
• Andractim (TN)
• 5-a-Androstanolone
• 5alpha-Androstanolone
• 5a-Dihydrotestosterone
• Androstanolone (DHT)
• 17-.beta.-Hydroxy-5-.alpha.-androstan-3-one
• 5-alpha-Androstanolone
• 1d2s
• 1t5z
• 1t7r
• STANOLONE [MI]
• (5.alpha.,17.beta.)-17-Hydroxy-androstan-3-one
• 4,5a-Dihydrotestosterone
• Androstan-17b-ol-3-one
• Epitope ID:135868
• 17-Hydroxyandrostan-3-one, (5.alpha.,17.beta.)- #
• EC 208-307-3
• 17b-Hydroxy-3-androstanone
• BIDD:PXR0075
• SCHEMBL15163
• 17-Hydroxy-androstan-3-one
• MLS001304063
• 5a-Androstan-17b-ol-3-one
• BIDD:ER0136
• 5.alpha.-Dihydroxytestosterone
• 5A-Androstan-3-on-17B-ol
• 5B-Androstan-3-on-17B-ol
• ANDROSTANOLONE [MART.]
• GTPL2856
• GTPL3455
• ANDROSTANOLONE [WHO-DD]
• BDBM18161
• 1t63
• (+)-Androstan-17beta-ol-3-one
• HMS2272H05
• AMY22298
• HY-A0120
• NSC10972
• Tox21_111056
• Tox21_200987
• Tox21_303655
• BDBM50366473
• LMST02020042
• s4757
• AKOS015894892
• CCG-267385
• CS-5096
• DB02901
• GS-6587
• NCGC00091013-02
• NCGC00091013-03
• NCGC00257456-01
• NCGC00258540-01
• 17beta-hydroxy-3-oxo-5alpha-androstanone
• AC-16144
• AC-33095
• SMR000058342
• TESTOSTERONE IMPURITY F [EP IMPURITY]
• 5alpha-Androstan-17beta-ol-3-one, >=97.5%
• C03917
• D07456
• 5Alpha-Dihydrotestosterone, 1mg/ml in Acetonitrile
• Q411054
• 17.BETA.-HYDROXY-5.ALPHA.-ANDROSTAN-3-ONE
• 17.BETA.-HYDROXY-5.ALPHA.-ANDROSTANE-3-ONE
• Androstanolone (5alpha-Dihydrotestosterone, Stanolone)
• 5alpha-Androstan-17beta-ol-3-one, purum, >=99.0% (TLC)
• 5alpha-Androstan-17beta-ol-3-one, VETRANAL(TM), analytical standard
• Androstanolone (5alpha-Dihydrotestosterone, Stanolone) 1.0 mg/ml in Acetonitrile
• (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadecan-5-one
• (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-one
• (5S,8R,10S,13S,17S)-17-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one
• 17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,10,11,12,13,14,15,16, 17-hexadecahydrocyclopenta[a]phenanthren-3-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7262	72.62%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6935	69.35%
OATP2B1 inhibitior	-	0.8704	87.04%
OATP1B1 inhibitior	+	0.9123	91.23%
OATP1B3 inhibitior	+	0.9765	97.65%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.9500	95.00%
BSEP inhibitior	+	0.5753	57.53%
P-glycoprotein inhibitior	-	0.5785	57.85%
P-glycoprotein substrate	-	0.7392	73.92%
CYP3A4 substrate	+	0.7254	72.54%
CYP2C9 substrate	-	0.5308	53.08%
CYP2D6 substrate	-	0.7538	75.38%
CYP3A4 inhibition	-	0.8546	85.46%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9710	97.10%
CYP1A2 inhibition	-	0.6853	68.53%
CYP2C8 inhibition	-	0.9332	93.32%
CYP inhibitory promiscuity	-	0.9647	96.47%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5215	52.15%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9022	90.22%
Skin irritation	+	0.7045	70.45%
Skin corrosion	-	0.9031	90.31%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7753	77.53%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	+	0.9247	92.47%
skin sensitisation	-	0.6182	61.82%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8583	85.83%
Acute Oral Toxicity (c)	III	0.7855	78.55%
Estrogen receptor binding	+	0.9106	91.06%
Androgen receptor binding	+	0.8697	86.97%
Thyroid receptor binding	+	0.8462	84.62%
Glucocorticoid receptor binding	+	0.8975	89.75%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	-	0.6944	69.44%
Honey bee toxicity	-	0.8676	86.76%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9434	94.34%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1871	P10275	Androgen Receptor	0.05 nM	IC50	via Super-PRED
CHEMBL1978	P11511	Cytochrome P450 19A1	220 nM	Ki	via Super-PRED
CHEMBL2034	P04150	Glucocorticoid receptor	540 nM	IC50	via Super-PRED
CHEMBL1994	P08235	Mineralocorticoid receptor	360 nM	IC50	via Super-PRED
CHEMBL3305	P04278	Testis-specific androgen-binding protein	0.182 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.71%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.47%	91.11%
CHEMBL204	P00734	Thrombin	91.66%	96.01%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.02%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.30%	98.95%
CHEMBL1902	P62942	FK506-binding protein 1A	85.39%	97.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.93%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.41%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.19%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.04%	96.38%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.89%	92.94%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.59%	85.11%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10635
• LOTUS: LTS0189879
• wikiData: Q411054