(3S,4aS,6aR,6bS,9S,11aS,11bR)-9-[(1S)-1-[(2R,5S)-1,5-dimethylpiperidin-2-yl]ethyl]-3-hydroxy-10,11b-dimethyl-2,3,4,4a,6,6a,6b,7,8,9,11,11a-dodecahydro-1H-benzo[a]fluoren-5-one

Details

• Internal ID: 3db6b1f2-e524-4bcc-9beb-b3d8e6a011ea
• Taxonomy: Organoheterocyclic compounds > Piperidines
• IUPAC Name: (3S,4aS,6aR,6bS,9S,11aS,11bR)-9-[(1S)-1-[(2R,5S)-1,5-dimethylpiperidin-2-yl]ethyl]-3-hydroxy-10,11b-dimethyl-2,3,4,4a,6,6a,6b,7,8,9,11,11a-dodecahydro-1H-benzo[a]fluoren-5-one
• SMILES (Canonical): CC1CCC(N(C1)C)C(C)C2CCC3C4CC(=O)C5CC(CCC5(C4CC3=C2C)C)O
• SMILES (Isomeric): C[C@H]1CC[C@@H](N(C1)C)[C@@H](C)[C@@H]2CC[C@H]3[C@@H]4CC(=O)[C@H]5C[C@H](CC[C@@]5([C@H]4CC3=C2C)C)O
• InChI: InChI=1S/C28H45NO2/c1-16-6-9-26(29(5)15-16)18(3)20-7-8-21-22(17(20)2)13-24-23(21)14-27(31)25-12-19(30)10-11-28(24,25)4/h16,18-21,23-26,30H,6-15H2,1-5H3/t16-,18-,19-,20+,21+,23-,24-,25+,26+,28+/m0/s1
• InChI Key: ZQRCSCBRFOPBME-AYYYJXAZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₅NO₂
• Molecular Weight: 427.70 g/mol
• Exact Mass: 427.345029678 g/mol
• Topological Polar Surface Area (TPSA): 40.50 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 5.47
• 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	+	0.9922	99.22%
Caco-2	+	0.6039	60.39%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5560	55.60%
OATP2B1 inhibitior	-	0.7174	71.74%
OATP1B1 inhibitior	+	0.8737	87.37%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9062	90.62%
P-glycoprotein inhibitior	-	0.5674	56.74%
P-glycoprotein substrate	+	0.6955	69.55%
CYP3A4 substrate	+	0.7200	72.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4463	44.63%
CYP3A4 inhibition	-	0.7879	78.79%
CYP2C9 inhibition	-	0.8921	89.21%
CYP2C19 inhibition	-	0.9344	93.44%
CYP2D6 inhibition	-	0.5250	52.50%
CYP1A2 inhibition	-	0.8756	87.56%
CYP2C8 inhibition	-	0.8394	83.94%
CYP inhibitory promiscuity	-	0.9758	97.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5488	54.88%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9419	94.19%
Skin irritation	-	0.6845	68.45%
Skin corrosion	-	0.8745	87.45%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5065	50.65%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	-	0.5414	54.14%
skin sensitisation	-	0.8166	81.66%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.8632	86.32%
Acute Oral Toxicity (c)	III	0.5285	52.85%
Estrogen receptor binding	+	0.6868	68.68%
Androgen receptor binding	+	0.7825	78.25%
Thyroid receptor binding	-	0.5228	52.28%
Glucocorticoid receptor binding	+	0.7669	76.69%
Aromatase binding	-	0.4879	48.79%
PPAR gamma	-	0.5254	52.54%
Honey bee toxicity	-	0.7375	73.75%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	-	0.4051	40.51%

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	97.38%	97.25%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	97.13%	95.58%
CHEMBL4072	P07858	Cathepsin B	97.06%	93.67%
CHEMBL2581	P07339	Cathepsin D	94.24%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.98%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.03%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.99%	90.71%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.38%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.38%	96.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.76%	96.47%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	90.10%	98.46%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.64%	93.00%
CHEMBL238	Q01959	Dopamine transporter	89.04%	95.88%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.66%	97.09%
CHEMBL325	Q13547	Histone deacetylase 1	87.68%	95.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.27%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	87.21%	90.17%
CHEMBL5103	Q969S8	Histone deacetylase 10	86.66%	90.08%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.61%	100.00%
CHEMBL3837	P07711	Cathepsin L	85.86%	96.61%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.62%	89.05%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.62%	93.56%
CHEMBL1937	Q92769	Histone deacetylase 2	85.46%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.23%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.54%	85.14%
CHEMBL1075317	P61964	WD repeat-containing protein 5	83.47%	96.33%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.23%	91.03%
CHEMBL1871	P10275	Androgen Receptor	82.68%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.54%	89.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.48%	92.86%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.12%	96.38%
CHEMBL4506	Q96EB6	NAD-dependent deacetylase sirtuin 1	81.76%	88.33%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.76%	98.75%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.71%	94.78%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.67%	86.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.12%	85.00%
CHEMBL4073	P09237	Matrix metalloproteinase 7	80.06%	97.56%

Plants that contains it

• Fritillaria imperialis

Cross-Links

• PubChem: 162922854
• LOTUS: LTS0052768
• wikiData: Q105381684