(3S,5S,8S,9S,10R,13S,14S,17R)-17-[(1S)-1-[(2R,5S)-1,5-dimethylpiperidin-2-yl]ethyl]-3-hydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one

Details

• Internal ID: 079bb053-cd4b-4354-b195-4f70894d31b1
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal alkaloids > 22,26-epiminocholestanes
• IUPAC Name: (3S,5S,8S,9S,10R,13S,14S,17R)-17-[(1S)-1-[(2R,5S)-1,5-dimethylpiperidin-2-yl]ethyl]-3-hydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC1CCC(N(C1)C)C(C)C2CCC3C2(CCC4C3CC(=O)C5C4(CCC(C5)O)C)C
• SMILES (Isomeric): C[C@H]1CC[C@@H](N(C1)C)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC(=O)[C@@H]5[C@@]4(CC[C@@H](C5)O)C)C
• InChI: InChI=1S/C28H47NO2/c1-17-6-9-25(29(5)16-17)18(2)21-7-8-22-20-15-26(31)24-14-19(30)10-12-28(24,4)23(20)11-13-27(21,22)3/h17-25,30H,6-16H2,1-5H3/t17-,18-,19-,20-,21+,22-,23-,24+,25+,27+,28+/m0/s1
• InChI Key: HEOBUSMYCWXIQQ-NGLBEBEOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₇NO₂
• Molecular Weight: 429.70 g/mol
• Exact Mass: 429.360679742 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 5.55
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9864	98.64%
Caco-2	+	0.5197	51.97%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.4559	45.59%
OATP2B1 inhibitior	-	0.5780	57.80%
OATP1B1 inhibitior	+	0.8308	83.08%
OATP1B3 inhibitior	+	0.9442	94.42%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.6845	68.45%
P-glycoprotein inhibitior	-	0.6368	63.68%
P-glycoprotein substrate	+	0.6211	62.11%
CYP3A4 substrate	+	0.7401	74.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	-	0.6538	65.38%
CYP2C9 inhibition	-	0.8949	89.49%
CYP2C19 inhibition	-	0.9405	94.05%
CYP2D6 inhibition	-	0.6198	61.98%
CYP1A2 inhibition	-	0.8697	86.97%
CYP2C8 inhibition	-	0.8906	89.06%
CYP inhibitory promiscuity	-	0.9921	99.21%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6433	64.33%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9490	94.90%
Skin irritation	-	0.6984	69.84%
Skin corrosion	-	0.8349	83.49%
Ames mutagenesis	-	0.7570	75.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4833	48.33%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.5311	53.11%
skin sensitisation	-	0.8534	85.34%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.8469	84.69%
Acute Oral Toxicity (c)	III	0.5338	53.38%
Estrogen receptor binding	+	0.7776	77.76%
Androgen receptor binding	+	0.8032	80.32%
Thyroid receptor binding	+	0.5275	52.75%
Glucocorticoid receptor binding	+	0.7066	70.66%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	-	0.5721	57.21%
Honey bee toxicity	-	0.7387	73.87%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	-	0.7482	74.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.28%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.81%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.24%	96.77%
CHEMBL2581	P07339	Cathepsin D	94.06%	98.95%
CHEMBL238	Q01959	Dopamine transporter	93.65%	95.88%
CHEMBL4072	P07858	Cathepsin B	92.85%	93.67%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	92.12%	95.58%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.83%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	90.46%	98.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.32%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.70%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.12%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.87%	93.56%
CHEMBL3837	P07711	Cathepsin L	86.77%	96.61%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.60%	93.04%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.57%	82.69%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.30%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.20%	93.00%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	85.85%	94.78%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.59%	85.11%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.01%	100.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	83.52%	98.46%
CHEMBL1871	P10275	Androgen Receptor	83.33%	96.43%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.03%	91.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.39%	97.14%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.18%	89.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.05%	95.89%
CHEMBL3045	P05771	Protein kinase C beta	81.90%	97.63%
CHEMBL1914	P06276	Butyrylcholinesterase	81.49%	95.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.47%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	81.21%	90.17%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.41%	98.33%
CHEMBL5255	O00206	Toll-like receptor 4	80.25%	92.50%

Plants that contains it

• Fritillaria cirrhosa
• Fritillaria delavayi
• Fritillaria monantha
• Fritillaria pallidiflora
• Fritillaria przewalskii
• Fritillaria taipaiensis
• Fritillaria unibracteata
• Fritillaria verticillata
• Fritillaria walujewii

Cross-Links

• PubChem: 10693900
• NPASS: NPC105255