(13S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol

Details

• Internal ID: 781c2e4f-ebbe-4e69-bb0f-bdf471f0c8e1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Estrane steroids > Estrogens and derivatives
• IUPAC Name: (13S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
• SMILES (Canonical): CC12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
• SMILES (Isomeric): C[C@]12CCC3C(C1CC(C2O)O)CCC4=C3C=CC(=C4)O
• InChI: InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13?,14?,15?,16?,17?,18-/m0/s1
• InChI Key: PROQIPRRNZUXQM-KXGAMWBWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₄O₃
• Molecular Weight: 288.40 g/mol
• Exact Mass: 288.17254462 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• AKOS025310086
• NCGC00094674-01
• NCGC00094674-02
• A828047
• (13S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9962	99.62%
Caco-2	+	0.7925	79.25%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7869	78.69%
OATP2B1 inhibitior	-	0.8840	88.40%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9672	96.72%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8666	86.66%
P-glycoprotein inhibitior	-	0.9448	94.48%
P-glycoprotein substrate	+	0.7808	78.08%
CYP3A4 substrate	+	0.7444	74.44%
CYP2C9 substrate	+	0.6944	69.44%
CYP2D6 substrate	+	0.3779	37.79%
CYP3A4 inhibition	-	0.8932	89.32%
CYP2C9 inhibition	-	0.9399	93.99%
CYP2C19 inhibition	-	0.7086	70.86%
CYP2D6 inhibition	-	0.9619	96.19%
CYP1A2 inhibition	-	0.6618	66.18%
CYP2C8 inhibition	+	0.9459	94.59%
CYP inhibitory promiscuity	-	0.9152	91.52%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.6400	64.00%
Carcinogenicity (trinary)	Danger	0.3846	38.46%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9678	96.78%
Skin irritation	+	0.5780	57.80%
Skin corrosion	-	0.8547	85.47%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3979	39.79%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	+	0.9500	95.00%
skin sensitisation	-	0.8252	82.52%
Respiratory toxicity	+	0.9667	96.67%
Reproductive toxicity	+	1.0000	100.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.9398	93.98%
Acute Oral Toxicity (c)	III	0.5947	59.47%
Estrogen receptor binding	+	0.9075	90.75%
Androgen receptor binding	+	0.8696	86.96%
Thyroid receptor binding	+	0.7551	75.51%
Glucocorticoid receptor binding	+	0.8270	82.70%
Aromatase binding	+	0.7457	74.57%
PPAR gamma	-	0.6677	66.77%
Honey bee toxicity	-	0.8719	87.19%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6900	69.00%
Fish aquatic toxicity	+	0.9874	98.74%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL206	P03372	Estrogen receptor alpha	1.995 nM; 72 nM	EC50; EC50	via Super-PRED; via Super-PRED
CHEMBL242	Q92731	Estrogen receptor beta	0.1259 nM; 11 nM	EC50; EC50	via Super-PRED; via Super-PRED
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	79.4 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	223.9 nM	Potency	via Super-PRED
CHEMBL3305	P04278	Testis-specific androgen-binding protein	234.42 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.09%	91.11%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	97.86%	89.05%
CHEMBL226	P30542	Adenosine A1 receptor	97.17%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.28%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.10%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.96%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.34%	100.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	90.24%	91.79%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.10%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.01%	86.33%
CHEMBL238	Q01959	Dopamine transporter	88.90%	95.88%
CHEMBL2581	P07339	Cathepsin D	88.55%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.68%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.52%	97.25%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.70%	90.71%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.52%	97.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.47%	95.89%
CHEMBL217	P14416	Dopamine D2 receptor	84.02%	95.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.71%	89.62%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	82.87%	97.23%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.99%	100.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.85%	85.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.98%	93.40%

Plants that contains it

• Angelica decursiva
• Asarum sieboldii
• Foeniculum vulgare
• Zanthoxylum bungeanum

Cross-Links

• PubChem: 16757678
• NPASS: NPC214224