(1R,2S,4S,5'S,6S,7R,9S,12R,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-ol

Details

• Internal ID: d9f1a7b7-ac52-45ee-94e9-f20e82457f8b
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > Spirosolanes and derivatives
• IUPAC Name: (1R,2S,4S,5'S,6S,7R,9S,12R,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-ol
• SMILES (Canonical): CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)O)C)C)C)NC1
• SMILES (Isomeric): C[C@H]1CC[C@]2([C@@H](C3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)O)C)C)C)NC1
• InChI: InChI=1S/C27H45NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28-29H,5-15H2,1-4H3/t16-,17+,18-,19-,20+,21+,22-,23-,24?,25-,26-,27-/m0/s1
• InChI Key: XYNPYHXGMWJBLV-IAQRSOHTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₅NO₂
• Molecular Weight: 415.70 g/mol
• Exact Mass: 415.345029678 g/mol
• Topological Polar Surface Area (TPSA): 41.50 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 5.37
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9904	99.04%
Caco-2	-	0.5625	56.25%
Blood Brain Barrier	+	0.7879	78.79%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Lysosomes	0.5355	53.55%
OATP2B1 inhibitior	-	0.5716	57.16%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	-	0.4922	49.22%
P-glycoprotein inhibitior	-	0.6134	61.34%
P-glycoprotein substrate	-	0.5949	59.49%
CYP3A4 substrate	+	0.7144	71.44%
CYP2C9 substrate	-	0.7859	78.59%
CYP2D6 substrate	-	0.7002	70.02%
CYP3A4 inhibition	-	0.9681	96.81%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9354	93.54%
CYP2C8 inhibition	-	0.6302	63.02%
CYP inhibitory promiscuity	-	0.9450	94.50%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5808	58.08%
Eye corrosion	-	0.9867	98.67%
Eye irritation	-	0.9463	94.63%
Skin irritation	-	0.7721	77.21%
Skin corrosion	-	0.8912	89.12%
Ames mutagenesis	-	0.7454	74.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4544	45.44%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.7313	73.13%
skin sensitisation	-	0.8311	83.11%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7062	70.62%
Acute Oral Toxicity (c)	III	0.7096	70.96%
Estrogen receptor binding	+	0.7039	70.39%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	+	0.6964	69.64%
Glucocorticoid receptor binding	+	0.7683	76.83%
Aromatase binding	+	0.7302	73.02%
PPAR gamma	+	0.5858	58.58%
Honey bee toxicity	-	0.6871	68.71%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	-	0.8175	81.75%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4931	Q15125	3-beta-hydroxysteroid-delta(8),delta(7)-isomerase	583 nM	Ki	via Super-PRED
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	398.1 nM	Potency	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	96.00%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.76%	97.09%
CHEMBL204	P00734	Thrombin	95.10%	96.01%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	92.89%	89.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.66%	91.11%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	90.21%	97.31%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	89.91%	95.58%
CHEMBL238	Q01959	Dopamine transporter	89.38%	95.88%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.30%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.01%	100.00%
CHEMBL233	P35372	Mu opioid receptor	87.50%	97.93%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.21%	92.88%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.79%	92.94%
CHEMBL3045	P05771	Protein kinase C beta	86.15%	97.63%
CHEMBL1871	P10275	Androgen Receptor	85.95%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.74%	94.45%
CHEMBL237	P41145	Kappa opioid receptor	85.04%	98.10%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	85.03%	96.38%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	84.75%	98.99%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.02%	91.03%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.93%	96.61%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	82.57%	95.48%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.53%	96.95%
CHEMBL2996	Q05655	Protein kinase C delta	81.79%	97.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.34%	95.89%
CHEMBL4581	P52732	Kinesin-like protein 1	80.95%	93.18%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.80%	97.28%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.77%	93.04%
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	80.65%	95.42%
CHEMBL221	P23219	Cyclooxygenase-1	80.10%	90.17%
CHEMBL242	Q92731	Estrogen receptor beta	80.03%	98.35%

Plants that contains it

• Solanum lycopersicum

Cross-Links

• PubChem: 50987408
• NPASS: NPC49748