Epitestosterone

Details

• Internal ID: 0f5a9ba8-2eb0-418a-8978-91f6bc1a8b5e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Androstane steroids > Androgens and derivatives
• IUPAC Name: (8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• SMILES (Canonical): CC12CCC3C(C1CCC2O)CCC4=CC(=O)CCC34C
• SMILES (Isomeric): C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@H]2O)CCC4=CC(=O)CC[C@]34C
• 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/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17+,18-,19-/m0/s1
• InChI Key: MUMGGOZAMZWBJJ-KZYORJDKSA-N
• Popularity: 750 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₈O₂
• Molecular Weight: 288.40 g/mol
• Exact Mass: 288.208930132 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.88
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 481-30-1
• Isotestosterone
• cis-Testosterone
• 17-Epitestosterone
• epi-Testosterone
• 17-alpha-Testosterone
• 17alpha-Hydroxyandrost-4-en-3-one
• 17-epi-Testosterone
• NSC 26499
• 17.alpha.-Testosterone
• 17alpha-cis-Testosterone
• 17-alpha-Hydroxyandrost-4-en-3-one
• Testosterone, cis-
• alpha epitestosterone
• (17-alpha)-17-Hydroxyandrost-4-en-3-one
• 17alpha-Testosterone
• 17.alpha.-Hydroxyandrost-4-en-3-one
• (8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• DTXSID8022329
• CHEBI:42534
• NSC-26499
• 48L726977Z
• (10alpha,13alpha,14beta,17alpha)-17-Hydroxyandrost-4-En-3-One
• Androst-4-en-3-one, 17.alpha.-hydroxy-
• Androst-4-en-3-one, 17-hydroxy-, (17.alpha.)-
• 17alpha-Hydroxyandrost-4-en-3-one (Epitestosterone)
• BRN 1915396
• 4-Androsten-17.alpha.-ol-3-one
• UNII-48L726977Z
• NCGC00091018-01
• Androst-4-en-3-one, 17-hydroxy-, (17alpha)-
• 17a-cis-Testosterone
• Androst-4-en-3-one, 17alpha-hydroxy-
• 17-Hydroxyandrost-4-en-3-one, (17.alpha.)-
• ANDROST-4-EN-3-ONE, 17-alpha-HYDROXY-
• EPITESTOSTERONE [MI]
• Androst-4-en-3-one, 17-hydroxy-, (17-alpha)-
• BIDD:ER0485
• SCHEMBL334193
• CHEMBL196228
• DTXCID002329
• MUMGGOZAMZWBJJ-KZYORJDKSA-N
• 17.ALPHA.-CIS-TESTOSTERONE
• NSC26499
• Tox21_111058
• BDBM50410492
• LMST02020051
• DB07768
• Androst-4-en-3-one, (17.alpha.)-
• SMP2_000253
• NCGC00091018-02
• CAS-481-30-1
• (17alpha)-17-hydroxyandrost-4-en-3-one
• Epitestosterone 1.0 mg/ml in Acetonitrile
• 4-ANDROSTENE-17.ALPHA.-OL-3-ONE
• ANDROST-4-EN-17.ALPHA.-OL-3-ONE
• TESTOSTERONE IMPURITY C [EP IMPURITY]
• Q416852
• BRD-K25836724-001-01-6
• (8R,10R,13S,17R)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[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	+	0.8779	87.79%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7307	73.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9328	93.28%
OATP1B3 inhibitior	+	0.9834	98.34%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.7651	76.51%
BSEP inhibitior	+	0.8147	81.47%
P-glycoprotein inhibitior	+	0.6194	61.94%
P-glycoprotein substrate	-	0.9363	93.63%
CYP3A4 substrate	+	0.7980	79.80%
CYP2C9 substrate	+	1.0000	100.00%
CYP2D6 substrate	-	0.8653	86.53%
CYP3A4 inhibition	-	0.8812	88.12%
CYP2C9 inhibition	-	0.9500	95.00%
CYP2C19 inhibition	-	0.6668	66.68%
CYP2D6 inhibition	-	0.9452	94.52%
CYP1A2 inhibition	-	0.9005	90.05%
CYP2C8 inhibition	-	0.9883	98.83%
CYP inhibitory promiscuity	-	0.8683	86.83%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Warning	0.4896	48.96%
Eye corrosion	-	0.9939	99.39%
Eye irritation	-	0.9830	98.30%
Skin irritation	+	0.6475	64.75%
Skin corrosion	-	0.9598	95.98%
Ames mutagenesis	-	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6161	61.61%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	-	0.5379	53.79%
Respiratory toxicity	+	0.9889	98.89%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8918	89.18%
Acute Oral Toxicity (c)	III	0.5718	57.18%
Estrogen receptor binding	+	0.8997	89.97%
Androgen receptor binding	+	0.9202	92.02%
Thyroid receptor binding	+	0.8703	87.03%
Glucocorticoid receptor binding	+	0.9432	94.32%
Aromatase binding	+	0.8125	81.25%
PPAR gamma	-	0.6720	67.20%
Honey bee toxicity	-	0.8584	85.84%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9850	98.50%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1871	P10275	Androgen Receptor	2.7 nM	IC50	via Super-PRED
CHEMBL1978	P11511	Cytochrome P450 19A1	600 nM	Ki	via Super-PRED
CHEMBL4523454	Q9H255	Olfactory receptor 51E2	0.69 nM	EC50	via Super-PRED
CHEMBL3305	P04278	Testis-specific androgen-binding protein	0.631 nM	Kd	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	31.6 nM	Potency	via Super-PRED
CHEMBL1940	Q13936	Voltage-gated L-type calcium channel alpha-1C subunit	34 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1994	P08235	Mineralocorticoid receptor	97.25%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.81%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.09%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.36%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.67%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	85.51%	95.93%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	85.45%	94.78%
CHEMBL2581	P07339	Cathepsin D	84.96%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.45%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.86%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.28%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.90%	82.69%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.23%	92.94%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.19%	90.71%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.16%	85.30%

Plants that contains it

• Vitex agnus-castus

Cross-Links

• PubChem: 10204
• LOTUS: LTS0046173
• wikiData: Q416852