(4R)-4-(4,7-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-7,10-dimethoxy-1,2,3,4-tetrahydroindolo[2,3-a]quinolizine

Details

• Internal ID: 2e3aaa88-772f-48a8-9f34-d2d3cc1d6d5e
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: (4R)-4-(4,7-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-7,10-dimethoxy-1,2,3,4-tetrahydroindolo[2,3-a]quinolizine
• SMILES (Canonical): COC1=CC2=C(C=C1)C3=C(N2)C(=NC=C3OC)C4CCCC5=C6C(=C7C=CC(=CC7=N6)OC)C(=CN45)OC
• SMILES (Isomeric): COC1=CC2=C(C=C1)C3=C(N2)C(=NC=C3OC)[C@H]4CCCC5=C6C(=C7C=CC(=CC7=N6)OC)C(=CN45)OC
• InChI: InChI=1S/C30H28N4O4/c1-35-16-9-11-19-20(12-16)32-28-22-6-5-7-23(34(22)15-25(38-4)27(19)28)29-30-26(24(37-3)14-31-29)18-10-8-17(36-2)13-21(18)33-30/h8-15,23,33H,5-7H2,1-4H3/t23-/m1/s1
• InChI Key: ZLXVSSDCCKVREE-HSZRJFAPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₂₈N₄O₄
• Molecular Weight: 508.60 g/mol
• Exact Mass: 508.21105539 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 6.13
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	-	0.6961	69.61%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8391	83.91%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8796	87.96%
OATP1B3 inhibitior	+	0.9333	93.33%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.5221	52.21%
BSEP inhibitior	+	0.9911	99.11%
P-glycoprotein inhibitior	+	0.9185	91.85%
P-glycoprotein substrate	+	0.7256	72.56%
CYP3A4 substrate	+	0.6800	68.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7162	71.62%
CYP3A4 inhibition	+	0.8039	80.39%
CYP2C9 inhibition	-	0.7390	73.90%
CYP2C19 inhibition	-	0.6503	65.03%
CYP2D6 inhibition	-	0.6309	63.09%
CYP1A2 inhibition	+	0.7117	71.17%
CYP2C8 inhibition	+	0.8128	81.28%
CYP inhibitory promiscuity	+	0.9276	92.76%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6061	60.61%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9599	95.99%
Skin irritation	-	0.8163	81.63%
Skin corrosion	-	0.9446	94.46%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9032	90.32%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9196	91.96%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7716	77.16%
Acute Oral Toxicity (c)	III	0.5531	55.31%
Estrogen receptor binding	+	0.8272	82.72%
Androgen receptor binding	+	0.7965	79.65%
Thyroid receptor binding	+	0.7749	77.49%
Glucocorticoid receptor binding	+	0.8452	84.52%
Aromatase binding	+	0.6731	67.31%
PPAR gamma	+	0.7203	72.03%
Honey bee toxicity	-	0.8822	88.22%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	-	0.4812	48.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5747	Q92793	CREB-binding protein	99.00%	95.12%
CHEMBL3192	Q9BY41	Histone deacetylase 8	98.48%	93.99%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.47%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	96.94%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.48%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.48%	92.94%
CHEMBL1937	Q92769	Histone deacetylase 2	94.27%	94.75%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.93%	91.11%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	93.18%	97.31%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.65%	97.09%
CHEMBL325	Q13547	Histone deacetylase 1	92.61%	95.92%
CHEMBL1781	P11387	DNA topoisomerase I	92.42%	97.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.01%	95.56%
CHEMBL213	P08588	Beta-1 adrenergic receptor	91.96%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	91.31%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.26%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.99%	99.17%
CHEMBL2243	O00519	Anandamide amidohydrolase	89.97%	97.53%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	89.95%	91.79%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.87%	95.89%
CHEMBL202	P00374	Dihydrofolate reductase	89.82%	89.92%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.19%	86.33%
CHEMBL2535	P11166	Glucose transporter	89.04%	98.75%
CHEMBL284	P27487	Dipeptidyl peptidase IV	88.68%	95.69%
CHEMBL2000	P03952	Plasma kallikrein	87.98%	93.92%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	87.95%	85.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.28%	92.62%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	87.05%	92.38%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	86.78%	89.32%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.14%	94.45%
CHEMBL4302	P08183	P-glycoprotein 1	85.62%	92.98%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.53%	97.36%
CHEMBL1907	P15144	Aminopeptidase N	84.99%	93.31%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.69%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.55%	99.23%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.97%	95.78%
CHEMBL4208	P20618	Proteasome component C5	83.32%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.30%	89.62%
CHEMBL3438	Q05513	Protein kinase C zeta	80.90%	88.48%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.68%	99.18%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	80.68%	91.81%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.06%	96.00%

Plants that contains it

• Perriera madagascariensis

Cross-Links

• PubChem: 5324316
• LOTUS: LTS0128477
• wikiData: Q105379272