(3R,8S,10aS,11S,11aS)-8-[(4R,4aS,6S,8aR)-4,6-dihydroxy-1,8a-dimethyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl]-3,11-dimethyl-1,2,3,4,6a,7,8,9,10,10a,11,11a-dodecahydrobenzo[b]quinolizin-6-one

Details

• Internal ID: b14eb247-4183-43fe-953a-5ffdbd4773a1
• Taxonomy: Organoheterocyclic compounds > Isoquinolines and derivatives > Naphthylisoquinolines
• IUPAC Name: (3R,8S,10aS,11S,11aS)-8-[(4R,4aS,6S,8aR)-4,6-dihydroxy-1,8a-dimethyl-2,3,4,4a,5,6,7,8-octahydro-1H-naphthalen-2-yl]-3,11-dimethyl-1,2,3,4,6a,7,8,9,10,10a,11,11a-dodecahydrobenzo[b]quinolizin-6-one
• SMILES (Canonical): CC1CCC2C(C3CCC(CC3C(=O)N2C1)C4CC(C5CC(CCC5(C4C)C)O)O)C
• SMILES (Isomeric): C[C@@H]1CC[C@H]2[C@H]([C@@H]3CC[C@@H](CC3C(=O)N2C1)C4C[C@H]([C@H]5C[C@H](CC[C@@]5(C4C)C)O)O)C
• InChI: InChI=1S/C27H45NO3/c1-15-5-8-24-16(2)20-7-6-18(11-22(20)26(31)28(24)14-15)21-13-25(30)23-12-19(29)9-10-27(23,4)17(21)3/h15-25,29-30H,5-14H2,1-4H3/t15-,16+,17?,18+,19+,20+,21?,22?,23-,24+,25-,27-/m1/s1
• InChI Key: XZPRQKJVCMRJRU-ZYMYBQQJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₅NO₃
• Molecular Weight: 431.70 g/mol
• Exact Mass: 431.33994430 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 4.48
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9812	98.12%
Caco-2	-	0.6402	64.02%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7580	75.80%
OATP2B1 inhibitior	-	0.5772	57.72%
OATP1B1 inhibitior	+	0.8355	83.55%
OATP1B3 inhibitior	+	0.9497	94.97%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6064	60.64%
BSEP inhibitior	+	0.7427	74.27%
P-glycoprotein inhibitior	-	0.6879	68.79%
P-glycoprotein substrate	+	0.5592	55.92%
CYP3A4 substrate	+	0.7171	71.71%
CYP2C9 substrate	-	0.8202	82.02%
CYP2D6 substrate	-	0.8127	81.27%
CYP3A4 inhibition	-	0.8054	80.54%
CYP2C9 inhibition	-	0.8430	84.30%
CYP2C19 inhibition	-	0.8338	83.38%
CYP2D6 inhibition	-	0.8469	84.69%
CYP1A2 inhibition	-	0.8941	89.41%
CYP2C8 inhibition	-	0.8054	80.54%
CYP inhibitory promiscuity	-	0.9437	94.37%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6410	64.10%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9401	94.01%
Skin irritation	-	0.7469	74.69%
Skin corrosion	-	0.9141	91.41%
Ames mutagenesis	-	0.7678	76.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.6938	69.38%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5497	54.97%
skin sensitisation	-	0.8824	88.24%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	+	0.5354	53.54%
Acute Oral Toxicity (c)	III	0.5411	54.11%
Estrogen receptor binding	+	0.7183	71.83%
Androgen receptor binding	+	0.7504	75.04%
Thyroid receptor binding	-	0.4895	48.95%
Glucocorticoid receptor binding	+	0.7090	70.90%
Aromatase binding	-	0.5115	51.15%
PPAR gamma	-	0.5639	56.39%
Honey bee toxicity	-	0.8244	82.44%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	-	0.4022	40.22%

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	96.96%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.78%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.37%	97.09%
CHEMBL238	Q01959	Dopamine transporter	91.84%	95.88%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.69%	82.69%
CHEMBL1871	P10275	Androgen Receptor	88.37%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.03%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	87.25%	97.05%
CHEMBL284	P27487	Dipeptidyl peptidase IV	86.65%	95.69%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.23%	89.05%
CHEMBL221	P23219	Cyclooxygenase-1	84.98%	90.17%
CHEMBL2581	P07339	Cathepsin D	84.95%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.81%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.40%	96.77%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	84.09%	94.78%
CHEMBL1937	Q92769	Histone deacetylase 2	82.88%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.82%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.74%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.06%	93.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	81.06%	98.46%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.37%	85.11%
CHEMBL4394	Q9NYA1	Sphingosine kinase 1	80.23%	96.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.17%	97.14%

Plants that contains it

• Fritillaria monantha

Cross-Links

• PubChem: 6325354
• NPASS: NPC226879