(2R,13bS)-2,11,12-trimethoxy-1,2,5,6-tetrahydroindolo[7a,1-a]isoquinoline-3,8,9-trione

Details

• Internal ID: 08a3484d-49c5-4a9f-a31f-65ecbea88bf5
• Taxonomy: Alkaloids and derivatives > Erythrina alkaloids > Erythrinanes
• IUPAC Name: (2R,13bS)-2,11,12-trimethoxy-1,2,5,6-tetrahydroindolo[7a,1-a]isoquinoline-3,8,9-trione
• SMILES (Canonical): COC1CC23C(=CC1=O)CCN2C(=O)C(=O)C4=CC(=C(C=C34)OC)OC
• SMILES (Isomeric): CO[C@@H]1C[C@@]23C(=CC1=O)CCN2C(=O)C(=O)C4=CC(=C(C=C34)OC)OC
• InChI: InChI=1S/C19H19NO6/c1-24-14-7-11-12(8-15(14)25-2)19-9-16(26-3)13(21)6-10(19)4-5-20(19)18(23)17(11)22/h6-8,16H,4-5,9H2,1-3H3/t16-,19+/m1/s1
• InChI Key: QKDKQEMXPXECKA-APWZRJJASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₉NO₆
• Molecular Weight: 357.40 g/mol
• Exact Mass: 357.12123733 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.24
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	+	0.8206	82.06%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8578	85.78%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9071	90.71%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6322	63.22%
BSEP inhibitior	+	0.8526	85.26%
P-glycoprotein inhibitior	-	0.6203	62.03%
P-glycoprotein substrate	-	0.5218	52.18%
CYP3A4 substrate	+	0.6251	62.51%
CYP2C9 substrate	-	0.7914	79.14%
CYP2D6 substrate	-	0.8282	82.82%
CYP3A4 inhibition	-	0.8593	85.93%
CYP2C9 inhibition	-	0.7706	77.06%
CYP2C19 inhibition	-	0.7738	77.38%
CYP2D6 inhibition	-	0.8413	84.13%
CYP1A2 inhibition	-	0.6964	69.64%
CYP2C8 inhibition	-	0.8155	81.55%
CYP inhibitory promiscuity	-	0.6940	69.40%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5605	56.05%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9134	91.34%
Skin irritation	-	0.7766	77.66%
Skin corrosion	-	0.9374	93.74%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5651	56.51%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	-	0.5057	50.57%
skin sensitisation	-	0.8629	86.29%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4504	45.04%
Acute Oral Toxicity (c)	III	0.6206	62.06%
Estrogen receptor binding	+	0.7831	78.31%
Androgen receptor binding	+	0.6716	67.16%
Thyroid receptor binding	+	0.5263	52.63%
Glucocorticoid receptor binding	+	0.7561	75.61%
Aromatase binding	-	0.5497	54.97%
PPAR gamma	-	0.5140	51.40%
Honey bee toxicity	-	0.7213	72.13%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9202	92.02%

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	96.92%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.34%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.59%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.39%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.39%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.63%	93.40%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.00%	96.38%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	88.65%	94.78%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.13%	97.14%
CHEMBL220	P22303	Acetylcholinesterase	86.85%	94.45%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	86.55%	96.86%
CHEMBL5747	Q92793	CREB-binding protein	86.24%	95.12%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	85.82%	92.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.74%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.52%	86.33%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	85.38%	95.53%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.92%	93.99%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.80%	94.00%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	84.53%	82.38%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	84.41%	90.24%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.39%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.32%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.96%	82.69%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.90%	95.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.78%	89.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	82.49%	96.09%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.68%	91.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.66%	99.23%
CHEMBL4208	P20618	Proteasome component C5	80.32%	90.00%

Plants that contains it

• Erythrina subumbrans

Cross-Links

• PubChem: 24770438
• LOTUS: LTS0028211
• wikiData: Q105223023