(3S,5R,8R,9R,10R,13R,14R,15S)-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15-decahydro-1H-cyclopenta[a]phenanthrene-3,15-diol

Details

• Internal ID: 9f2899cb-ece3-44b8-a915-0e5692bc6aac
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Hydroxysteroids > 3-hydroxysteroids > 3-beta-hydroxysteroids
• IUPAC Name: (3S,5R,8R,9R,10R,13R,14R,15S)-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15-decahydro-1H-cyclopenta[a]phenanthrene-3,15-diol
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1O)C)CCC4C3(C(C=C4)O)C)C)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC[C@H]4[C@]3([C@H](C=C4)O)C)C)(C)C)O
• InChI: InChI=1S/C22H36O2/c1-19(2)15-10-13-21(4)16(20(15,3)12-11-17(19)23)8-6-14-7-9-18(24)22(14,21)5/h7,9,14-18,23-24H,6,8,10-13H2,1-5H3/t14-,15+,16-,17+,18+,20+,21-,22+/m1/s1
• InChI Key: JFYPLXOOAASGRS-TUUZUYIFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₆O₂
• Molecular Weight: 332.50 g/mol
• Exact Mass: 332.271530387 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 4.55
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• BDBM50447862

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7142	71.42%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5589	55.89%
OATP2B1 inhibitior	-	0.8581	85.81%
OATP1B1 inhibitior	+	0.9055	90.55%
OATP1B3 inhibitior	+	0.9421	94.21%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.6519	65.19%
P-glycoprotein inhibitior	-	0.8833	88.33%
P-glycoprotein substrate	-	0.9004	90.04%
CYP3A4 substrate	+	0.6127	61.27%
CYP2C9 substrate	-	0.6131	61.31%
CYP2D6 substrate	-	0.7305	73.05%
CYP3A4 inhibition	-	0.8981	89.81%
CYP2C9 inhibition	-	0.9084	90.84%
CYP2C19 inhibition	-	0.7777	77.77%
CYP2D6 inhibition	-	0.9652	96.52%
CYP1A2 inhibition	-	0.5393	53.93%
CYP2C8 inhibition	-	0.8269	82.69%
CYP inhibitory promiscuity	-	0.8020	80.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.5778	57.78%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9501	95.01%
Skin irritation	+	0.6095	60.95%
Skin corrosion	-	0.9514	95.14%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4653	46.53%
Micronuclear	-	0.9900	99.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	+	0.5501	55.01%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.8424	84.24%
Acute Oral Toxicity (c)	III	0.7551	75.51%
Estrogen receptor binding	+	0.7874	78.74%
Androgen receptor binding	+	0.5309	53.09%
Thyroid receptor binding	+	0.7366	73.66%
Glucocorticoid receptor binding	+	0.7135	71.35%
Aromatase binding	+	0.6716	67.16%
PPAR gamma	-	0.5288	52.88%
Honey bee toxicity	-	0.8149	81.49%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9780	97.80%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.03%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.43%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	86.89%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.68%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.87%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.85%	91.11%
CHEMBL2581	P07339	Cathepsin D	84.06%	98.95%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.03%	92.94%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.34%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.10%	94.45%

Plants that contains it

• Rosa rugosa

Cross-Links

• PubChem: 76317773
• NPASS: NPC11908
• LOTUS: LTS0273868
• wikiData: Q105127129