methyl 10-hydroxy-2,11-dimethoxy-2,3,5,6,8,9-hexahydro-1H-indolo[7a,1-a]isoquinoline-12-carboxylate

Details

• Internal ID: 94f929b7-4658-4a17-9155-8ebe18301b0d
• Taxonomy: Alkaloids and derivatives > Erythrina alkaloids > Erythrinanes
• IUPAC Name: methyl 10-hydroxy-2,11-dimethoxy-2,3,5,6,8,9-hexahydro-1H-indolo[7a,1-a]isoquinoline-12-carboxylate
• SMILES (Canonical): COC1CC=C2CCN3C2(C1)C4=C(CC3)C(=C(C(=C4)C(=O)OC)OC)O
• SMILES (Isomeric): COC1CC=C2CCN3C2(C1)C4=C(CC3)C(=C(C(=C4)C(=O)OC)OC)O
• InChI: InChI=1S/C20H25NO5/c1-24-13-5-4-12-6-8-21-9-7-14-16(20(12,21)11-13)10-15(19(23)26-3)18(25-2)17(14)22/h4,10,13,22H,5-9,11H2,1-3H3
• InChI Key: MMZBOILCDYNGKK-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.40 g/mol
• Exact Mass: 359.17327290 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.38
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9800	98.00%
Caco-2	+	0.8887	88.87%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7873	78.73%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8937	89.37%
OATP1B3 inhibitior	+	0.9207	92.07%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.7519	75.19%
P-glycoprotein inhibitior	-	0.4867	48.67%
P-glycoprotein substrate	-	0.5856	58.56%
CYP3A4 substrate	+	0.6479	64.79%
CYP2C9 substrate	-	0.6156	61.56%
CYP2D6 substrate	+	0.4084	40.84%
CYP3A4 inhibition	-	0.9652	96.52%
CYP2C9 inhibition	-	0.9033	90.33%
CYP2C19 inhibition	-	0.8995	89.95%
CYP2D6 inhibition	-	0.6521	65.21%
CYP1A2 inhibition	-	0.7744	77.44%
CYP2C8 inhibition	+	0.5058	50.58%
CYP inhibitory promiscuity	-	0.9225	92.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4591	45.91%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8863	88.63%
Skin irritation	-	0.7603	76.03%
Skin corrosion	-	0.9384	93.84%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4397	43.97%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.6474	64.74%
skin sensitisation	-	0.8419	84.19%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7950	79.50%
Acute Oral Toxicity (c)	III	0.5120	51.20%
Estrogen receptor binding	+	0.7609	76.09%
Androgen receptor binding	+	0.5553	55.53%
Thyroid receptor binding	+	0.5801	58.01%
Glucocorticoid receptor binding	+	0.8058	80.58%
Aromatase binding	+	0.6961	69.61%
PPAR gamma	+	0.7730	77.30%
Honey bee toxicity	-	0.8909	89.09%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9191	91.91%

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	99.03%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.76%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.34%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.30%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	87.83%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.32%	94.00%
CHEMBL4208	P20618	Proteasome component C5	86.67%	90.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.44%	93.40%
CHEMBL2535	P11166	Glucose transporter	86.12%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.37%	91.07%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.94%	94.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.77%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.34%	95.89%
CHEMBL5028	O14672	ADAM10	81.11%	97.50%

Plants that contains it

• Cocculus laurifolius

Cross-Links

• PubChem: 163041803
• LOTUS: LTS0238255
• wikiData: Q105168204