6,6',7-Trimethoxy-2-methyl-1',2'-didehydrooxyacanthan-12'-ol

Details

• Internal ID: 65cbab87-23ef-4ccc-aece-d4a6f3892176
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: (14S)-20,21,25-trimethoxy-15-methyl-8,23-dioxa-15,30-diazaheptacyclo[22.6.2.29,12.13,7.114,18.027,31.022,33]hexatriaconta-1(30),3(36),4,6,9(35),10,12(34),18,20,22(33),24,26,31-tridecaen-6-ol
• SMILES (Canonical): CN1CCC2=CC(=C(C3=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6=NCCC7=CC(=C(O3)C=C76)OC)O)OC)OC
• SMILES (Isomeric): CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6=NCCC7=CC(=C(O3)C=C76)OC)O)OC)OC
• InChI: InChI=1S/C36H36N2O6/c1-38-14-12-24-19-33(41-3)35(42-4)36-34(24)28(38)16-21-5-8-25(9-6-21)43-30-17-22(7-10-29(30)39)15-27-26-20-32(44-36)31(40-2)18-23(26)11-13-37-27/h5-10,17-20,28,39H,11-16H2,1-4H3/t28-/m0/s1
• InChI Key: LMRJRQYDISGTIE-NDEPHWFRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₃₆N₂O₆
• Molecular Weight: 592.70 g/mol
• Exact Mass: 592.25733687 g/mol
• Topological Polar Surface Area (TPSA): 82.00 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 6.68
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 12-O-Demethylcoclobine
• 6,6',7-trimethoxy-2-methyl-1',2'-didehydrooxyacanthan-12'-ol
• DTXSID60923140
• 2H-1,24:12,15-Dietheno-6,10-metheno-16H-pyrido(2',3':17,18)(1,10)dioxacycloeicosino(2,3,4-ij)isoquinolin-9-ol, 3,5,16a,17,18,19-hexahydro-21,22,26-trimethoxy-17-methyl-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7901	79.01%
Caco-2	-	0.5452	54.52%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.4703	47.03%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.9155	91.55%
OATP1B3 inhibitior	+	0.9403	94.03%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.9940	99.40%
P-glycoprotein inhibitior	+	0.9557	95.57%
P-glycoprotein substrate	+	0.6856	68.56%
CYP3A4 substrate	+	0.7147	71.47%
CYP2C9 substrate	-	0.6166	61.66%
CYP2D6 substrate	+	0.4532	45.32%
CYP3A4 inhibition	-	0.6487	64.87%
CYP2C9 inhibition	-	0.9224	92.24%
CYP2C19 inhibition	-	0.8854	88.54%
CYP2D6 inhibition	-	0.8767	87.67%
CYP1A2 inhibition	-	0.9002	90.02%
CYP2C8 inhibition	+	0.6256	62.56%
CYP inhibitory promiscuity	-	0.9777	97.77%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6411	64.11%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9525	95.25%
Skin irritation	-	0.7673	76.73%
Skin corrosion	-	0.9422	94.22%
Ames mutagenesis	+	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8802	88.02%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8702	87.02%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7694	76.94%
Acute Oral Toxicity (c)	III	0.7326	73.26%
Estrogen receptor binding	+	0.8374	83.74%
Androgen receptor binding	+	0.6939	69.39%
Thyroid receptor binding	+	0.7043	70.43%
Glucocorticoid receptor binding	+	0.8256	82.56%
Aromatase binding	+	0.6014	60.14%
PPAR gamma	+	0.7014	70.14%
Honey bee toxicity	-	0.7203	72.03%
Biodegradation	-	1.0000	100.00%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.8151	81.51%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.63%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.39%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	93.81%	91.49%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.09%	93.40%
CHEMBL261	P00915	Carbonic anhydrase I	92.08%	96.76%
CHEMBL217	P14416	Dopamine D2 receptor	91.68%	95.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.58%	95.89%
CHEMBL2056	P21728	Dopamine D1 receptor	91.41%	91.00%
CHEMBL2581	P07339	Cathepsin D	91.32%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.12%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	90.73%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.52%	99.17%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	90.10%	82.38%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.89%	93.99%
CHEMBL5747	Q92793	CREB-binding protein	88.63%	95.12%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.37%	92.94%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	87.69%	91.79%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.44%	94.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.40%	82.67%
CHEMBL2535	P11166	Glucose transporter	86.92%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.55%	99.15%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	83.92%	90.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.83%	96.77%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.53%	80.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.25%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.96%	89.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.72%	97.53%
CHEMBL1744525	P43490	Nicotinamide phosphoribosyltransferase	82.64%	96.25%
CHEMBL4208	P20618	Proteasome component C5	82.22%	90.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.88%	95.53%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.80%	100.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.63%	91.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.62%	99.23%

Plants that contains it

• Guatteria guianensis

Cross-Links

• PubChem: 189707
• LOTUS: LTS0016998
• wikiData: Q82897075