Androsterone

Details

• Internal ID: 67c10d43-68aa-4828-b710-f4f5231730af
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Androstane steroids > Androgens and derivatives
• IUPAC Name: (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-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/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1
• InChI Key: QGXBDMJGAMFCBF-HLUDHZFRSA-N
• Popularity: 4,744 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

• 53-41-8
• Androkinine
• Androtine
• 5alpha-Androsterone
• 3alpha-Hydroxy-5alpha-androstan-17-one
• cis-Androsterone
• Atromide ICI
• 3-Epihydroxyetioallocholan-17-one
• 5alpha-Androstane-3alpha-ol-17-one
• 3alpha-Hydroxyetioallocholan-17-one
• 3alpha-Hydroxy-17-androstanone
• Androstanon-3-alpha-ol-17-one
• 3-alpha-Hydroxy-17-androstanone
• 3-alpha-Hydroxy-5-alpha-androstan-17-one
• 3-alpha-Hydroxyetioallocholan-17-one
• 5-alpha-Androstan-3-alpha-ol-17-one
• 5alpha-Androstan-3alpha-ol-17-one
• Androstan-17-one, 3-hydroxy-, (3a,5a)-
• Androstan-17-one, 3-hydroxy-, (3alpha,5alpha)-
• 5alpha-Androstan-17-one, 3alpha-hydroxy-
• (3alpha,5alpha)-3-hydroxyandrostan-17-one
• CHEBI:16032
• 5.alpha.-Androsterone
• Androstan-17-one, 3-hydroxy-, (3-alpha,5-alpha)-
• 3.alpha.-Hydroxy-17-androstanone
• U 6036
• (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
• CHEMBL87285
• MLS000069394
• C24W7J5D5R
• DTXSID3036525
• 5-alpha-Androstan-17-one, 3-alpha-hydroxy-
• NSC 9898
• NSC-9898
• 3.alpha.-Hydroxyetioallocholan-17-one
• SMR000058571
• 5.alpha.-Androstane-3.alpha.-ol-17-one
• 5.alpha.-Androstan-17-one, 3.alpha.-hydroxy-
• d-Epiandrosterone
• 3-Epiandrosterone
• Androkinin
• Caswell No. 051G
• Androsterone, epi-
• Androsterone, trans-
• Androstan-17-one, 3-hydroxy-, (3.alpha.,5.alpha.)-
• Esterase basic kit
• (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-Dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one
• 3-Hydroxyandrostan-17-one
• EINECS 200-173-4
• EPA Pesticide Chemical Code 126501
• BRN 2217626
• UNII-C24W7J5D5R
• 3-.beta.Hydroxyandrostan-17-one
• Androsterolone
• CAS-53-41-8
• 5.alpha.-Androstan-3.beta.-ol-17-one
• AOI
• Prestwick_689
• 5-alpha-Androsterone
• 1x8j
• Opera_ID_584
• Prestwick0_000411
• Prestwick1_000411
• Prestwick2_000411
• Prestwick3_000411
• ANDROSTERONE [MI]
• bmse000543
• Epitope ID:174330
• UPCMLD-DP124
• 5-androstan-3-ol-17-one
• BSPBio_000362
• 4-08-00-00642 (Beilstein Handbook Reference)
• MLS000563085
• MLS001146886
• MLS002153256
• 5a-Androstan-3a-ol-17-one
• SCHEMBL269981
• SPBio_002301
• BPBio1_000400
• DTXCID1016525
• UPCMLD-DP124:001
• BDBM17639
• NSC9898
• HMS1569C04
• HMS2096C04
• HMS2230I18
• HMS3713C04
• HY-N0933
• Tox21_303701
• LMST02020001
• s6352
• 5-alpha-Androstane-3alpha-ol-17-one
• AKOS015894886
• CCG-220411
• GS-3614
• 3alpha-hydroxy-5alpha-androstane-17-one
• NCGC00161664-01
• NCGC00161664-02
• NCGC00357021-01
• 3-alpha-hydroxy-5alpha-Androstan-17-one
• AC-16145
• 3-alpha-Hydroxy-5-alpha-androstane-17-one
• A0646
• CS-0014230
• Androstan-17-one, 3alpha-hydroxy-, 5alpha-
• C00523
• D95612
• 3-hydroxy-(3-alpha,5-alpha)-Androstan-17-one
• Androsterone, VETRANAL(TM), analytical standard
• A923412
• Q422469
• SR-01000759187
• SR-01000759187-3
• 3.ALPHA.-HYDROXY-5.ALPHA.-ANDROSTAN-17-ONE
• (3.ALPHA.,5.ALPHA.)-3-HYDROXYANDROSTAN-17-ONE
• 086DA2D0-D9AE-4593-9E08-991AF2BF2A47
• '(3alpha,5beta,8alpha,10alpha,13alpha,14beta)-3-hydroxyandrostan-17-one'
• (3alpha,5beta,8alpha,10alpha,13alpha,14beta)-3-hydroxyandrostan-17-one
• (1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadecan-14-one
• (1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-one
• (1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
• (3R,5S,8R,10S,13S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7232	72.32%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6935	69.35%
OATP2B1 inhibitior	-	0.8652	86.52%
OATP1B1 inhibitior	+	0.9077	90.77%
OATP1B3 inhibitior	+	0.9765	97.65%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.9500	95.00%
BSEP inhibitior	+	0.5518	55.18%
P-glycoprotein inhibitior	-	0.7636	76.36%
P-glycoprotein substrate	-	0.8029	80.29%
CYP3A4 substrate	+	0.6949	69.49%
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	-	0.8214	82.14%
CYP inhibitory promiscuity	-	0.9647	96.47%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5215	52.15%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9109	91.09%
Skin irritation	+	0.7045	70.45%
Skin corrosion	-	0.9031	90.31%
Ames mutagenesis	-	0.9154	91.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7497	74.97%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	+	0.6840	68.40%
skin sensitisation	-	0.6182	61.82%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7611	76.11%
Acute Oral Toxicity (c)	III	0.7855	78.55%
Estrogen receptor binding	+	0.8916	89.16%
Androgen receptor binding	+	0.8484	84.84%
Thyroid receptor binding	+	0.7643	76.43%
Glucocorticoid receptor binding	+	0.9205	92.05%
Aromatase binding	+	0.7688	76.88%
PPAR gamma	-	0.7308	73.08%
Honey bee toxicity	-	0.8128	81.28%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9434	94.34%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4234	P37058	Estradiol 17-beta-dehydrogenase 3	330 nM	IC50	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	707.9 nM; 501.2 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL3305	P04278	Testis-specific androgen-binding protein	70.79 nM; 707.95 nM	Kd; Kd	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1994	P08235	Mineralocorticoid receptor	91.91%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.50%	96.09%
CHEMBL1871	P10275	Androgen Receptor	90.95%	96.43%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.76%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.18%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.42%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.87%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	85.61%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.49%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.22%	93.04%
CHEMBL204	P00734	Thrombin	83.78%	96.01%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.98%	82.69%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.24%	90.71%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.40%	93.03%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5879
• LOTUS: LTS0154084
• wikiData: Q422469