2,3,6-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizine

Details

• Internal ID: 3c8a64e9-bbcb-41d4-a78f-1234f07da9ff
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Phenanthroquinolizidines
• IUPAC Name: 2,3,6-trimethoxy-11,12,13,14,14a,15-hexahydro-9H-phenanthro[9,10-b]quinolizine
• SMILES (Canonical): COC1=CC2=C(C=C1)C3=C(CC4CCCCN4C3)C5=CC(=C(C=C52)OC)OC
• SMILES (Isomeric): COC1=CC2=C(C=C1)C3=C(CC4CCCCN4C3)C5=CC(=C(C=C52)OC)OC
• InChI: InChI=1S/C24H27NO3/c1-26-16-7-8-17-19(11-16)21-13-24(28-3)23(27-2)12-20(21)18-10-15-6-4-5-9-25(15)14-22(17)18/h7-8,11-13,15H,4-6,9-10,14H2,1-3H3
• InChI Key: RSHYSOGXGSUUIJ-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₇NO₃
• Molecular Weight: 377.50 g/mol
• Exact Mass: 377.19909372 g/mol
• Topological Polar Surface Area (TPSA): 30.90 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.93
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• SCHEMBL12015053

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9826	98.26%
Caco-2	+	0.8934	89.34%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7406	74.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9270	92.70%
OATP1B3 inhibitior	+	0.9602	96.02%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	+	0.9706	97.06%
P-glycoprotein inhibitior	+	0.8433	84.33%
P-glycoprotein substrate	+	0.6343	63.43%
CYP3A4 substrate	+	0.5742	57.42%
CYP2C9 substrate	+	0.7753	77.53%
CYP2D6 substrate	+	0.8760	87.60%
CYP3A4 inhibition	-	0.8353	83.53%
CYP2C9 inhibition	-	0.9089	90.89%
CYP2C19 inhibition	-	0.7153	71.53%
CYP2D6 inhibition	+	0.7634	76.34%
CYP1A2 inhibition	+	0.5409	54.09%
CYP2C8 inhibition	-	0.6428	64.28%
CYP inhibitory promiscuity	-	0.7447	74.47%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6386	63.86%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9733	97.33%
Skin irritation	-	0.7407	74.07%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9117	91.17%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.9029	90.29%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.7098	70.98%
Acute Oral Toxicity (c)	II	0.6963	69.63%
Estrogen receptor binding	+	0.7466	74.66%
Androgen receptor binding	+	0.6843	68.43%
Thyroid receptor binding	+	0.6691	66.91%
Glucocorticoid receptor binding	+	0.7744	77.44%
Aromatase binding	+	0.6541	65.41%
PPAR gamma	-	0.6253	62.53%
Honey bee toxicity	-	0.8803	88.03%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.7700	77.00%
Fish aquatic toxicity	-	0.4360	43.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3438	Q05513	Protein kinase C zeta	95.76%	88.48%
CHEMBL2535	P11166	Glucose transporter	94.96%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.85%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.41%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.09%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.17%	95.56%
CHEMBL5747	Q92793	CREB-binding protein	93.05%	95.12%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	92.78%	89.62%
CHEMBL5203	P33316	dUTP pyrophosphatase	91.97%	99.18%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	90.18%	90.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.70%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.54%	86.33%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	87.27%	91.43%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.07%	91.11%
CHEMBL1907	P15144	Aminopeptidase N	86.14%	93.31%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.02%	92.62%
CHEMBL4208	P20618	Proteasome component C5	85.94%	90.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.80%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.83%	94.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	83.61%	91.79%
CHEMBL2581	P07339	Cathepsin D	83.22%	98.95%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.09%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.64%	94.45%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.53%	96.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	82.07%	95.53%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.67%	92.38%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	80.58%	96.47%
CHEMBL1871	P10275	Androgen Receptor	80.29%	96.43%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.24%	91.03%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	80.11%	92.67%

Plants that contains it

• Cryptocarya pleurosperma

Cross-Links

• PubChem: 3750957
• LOTUS: LTS0237278
• wikiData: Q105244663