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(2R,3R,12bS)-3-ethenyl-9-methoxy-2-[(6-methoxy-9H-pyrido[3,4-b]indol-1-yl)methyl]-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID c2235f2c-32e2-445d-af10-f68fd5b911aa
Taxonomy Alkaloids and derivatives > Harmala alkaloids
IUPAC Name (2R,3R,12bS)-3-ethenyl-9-methoxy-2-[(6-methoxy-9H-pyrido[3,4-b]indol-1-yl)methyl]-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine
SMILES (Canonical) COC1=CC2=C(C=C1)NC3=C2CCN4C3CC(C(C4)C=C)CC5=NC=CC6=C5NC7=C6C=C(C=C7)OC
SMILES (Isomeric) COC1=CC2=C(C=C1)NC3=C2CCN4[C@H]3C[C@@H]([C@H](C4)C=C)CC5=NC=CC6=C5NC7=C6C=C(C=C7)OC
InChI InChI=1S/C31H32N4O2/c1-4-18-17-35-12-10-23-25-16-21(37-3)6-8-27(25)34-31(23)29(35)14-19(18)13-28-30-22(9-11-32-28)24-15-20(36-2)5-7-26(24)33-30/h4-9,11,15-16,18-19,29,33-34H,1,10,12-14,17H2,2-3H3/t18-,19-,29-/m0/s1
InChI Key HJDMYPURJXUHSR-GWZHAIQQSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C31H32N4O2
Molecular Weight 492.60 g/mol
Exact Mass 492.25252628 g/mol
Topological Polar Surface Area (TPSA) 66.20 Ų
XlogP 5.60
Atomic LogP (AlogP) 6.18
H-Bond Acceptor 4
H-Bond Donor 2
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R,3R,12bS)-3-ethenyl-9-methoxy-2-[(6-methoxy-9H-pyrido[3,4-b]indol-1-yl)methyl]-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9898 98.98%
Caco-2 - 0.7119 71.19%
Blood Brain Barrier + 0.7650 76.50%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.8430 84.30%
OATP2B1 inhibitior - 0.7138 71.38%
OATP1B1 inhibitior + 0.8919 89.19%
OATP1B3 inhibitior + 0.9309 93.09%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior + 0.6250 62.50%
BSEP inhibitior + 0.9962 99.62%
P-glycoprotein inhibitior + 0.9506 95.06%
P-glycoprotein substrate + 0.8241 82.41%
CYP3A4 substrate + 0.6941 69.41%
CYP2C9 substrate - 0.6106 61.06%
CYP2D6 substrate + 0.6788 67.88%
CYP3A4 inhibition + 0.6500 65.00%
CYP2C9 inhibition - 0.8164 81.64%
CYP2C19 inhibition - 0.7086 70.86%
CYP2D6 inhibition + 0.9120 91.20%
CYP1A2 inhibition + 0.6135 61.35%
CYP2C8 inhibition + 0.5317 53.17%
CYP inhibitory promiscuity + 0.8352 83.52%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6544 65.44%
Eye corrosion - 0.9891 98.91%
Eye irritation - 0.9464 94.64%
Skin irritation - 0.6946 69.46%
Skin corrosion - 0.9310 93.10%
Ames mutagenesis - 0.6100 61.00%
Human Ether-a-go-go-Related Gene inhibition + 0.9455 94.55%
Micronuclear + 0.6200 62.00%
Hepatotoxicity + 0.6199 61.99%
skin sensitisation - 0.8830 88.30%
Respiratory toxicity + 0.7889 78.89%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.9250 92.50%
Nephrotoxicity + 0.4560 45.60%
Acute Oral Toxicity (c) III 0.4621 46.21%
Estrogen receptor binding + 0.7768 77.68%
Androgen receptor binding + 0.8223 82.23%
Thyroid receptor binding + 0.6739 67.39%
Glucocorticoid receptor binding + 0.7762 77.62%
Aromatase binding + 0.6433 64.33%
PPAR gamma + 0.6508 65.08%
Honey bee toxicity - 0.7668 76.68%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity + 0.6100 61.00%
Fish aquatic toxicity + 0.8604 86.04%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL240 Q12809 HERG 99.43% 89.76%
CHEMBL1951 P21397 Monoamine oxidase A 99.21% 91.49%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.15% 96.09%
CHEMBL5747 Q92793 CREB-binding protein 98.94% 95.12%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 98.09% 93.40%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.91% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.10% 91.11%
CHEMBL241 Q14432 Phosphodiesterase 3A 96.48% 92.94%
CHEMBL3192 Q9BY41 Histone deacetylase 8 96.45% 93.99%
CHEMBL1907 P15144 Aminopeptidase N 94.11% 93.31%
CHEMBL3137262 O60341 LSD1/CoREST complex 92.87% 97.09%
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 89.73% 95.17%
CHEMBL255 P29275 Adenosine A2b receptor 89.72% 98.59%
CHEMBL4208 P20618 Proteasome component C5 89.59% 90.00%
CHEMBL2243 O00519 Anandamide amidohydrolase 89.26% 97.53%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.19% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.79% 95.56%
CHEMBL4302 P08183 P-glycoprotein 1 88.36% 92.98%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 86.49% 94.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 85.16% 99.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 85.13% 95.89%
CHEMBL1938212 Q9UPP1 Histone lysine demethylase PHF8 84.99% 98.33%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 84.56% 91.71%
CHEMBL4145 Q9UKV0 Histone deacetylase 9 84.46% 85.49%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 83.94% 91.03%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.06% 86.33%
CHEMBL1907598 P05106 Integrin alpha-V/beta-3 81.71% 95.71%
CHEMBL2535 P11166 Glucose transporter 81.36% 98.75%
CHEMBL1744525 P43490 Nicotinamide phosphoribosyltransferase 80.80% 96.25%
CHEMBL2581 P07339 Cathepsin D 80.77% 98.95%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.68% 100.00%
CHEMBL1781 P11387 DNA topoisomerase I 80.59% 97.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.23% 95.89%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Cinchona calisaya

Cross-Links

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PubChem 163187857
LOTUS LTS0181256
wikiData Q105029164