(2R,9R,13bS)-2,11,12-trimethoxy-7-oxido-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-7-ium-9-ol

Details

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Internal ID 39dba5ec-2c6a-44f1-8906-3f464dfb092a
Taxonomy Alkaloids and derivatives > Erythrina alkaloids > Erythrinanes
IUPAC Name (2R,9R,13bS)-2,11,12-trimethoxy-7-oxido-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-7-ium-9-ol
SMILES (Canonical) COC1CC23C(=CC[N+]2(CC(C4=CC(=C(C=C34)OC)OC)O)[O-])C=C1
SMILES (Isomeric) CO[C@@H]1C[C@@]23C(=CC[N+]2(C[C@@H](C4=CC(=C(C=C34)OC)OC)O)[O-])C=C1
InChI InChI=1S/C19H23NO5/c1-23-13-5-4-12-6-7-20(22)11-16(21)14-8-17(24-2)18(25-3)9-15(14)19(12,20)10-13/h4-6,8-9,13,16,21H,7,10-11H2,1-3H3/t13-,16-,19-,20?/m0/s1
InChI Key DWXDTNCZRDEMJI-YNCSRZAISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C19H23NO5
Molecular Weight 345.40 g/mol
Exact Mass 345.15762283 g/mol
Topological Polar Surface Area (TPSA) 66.00 Ų
XlogP 0.50
Atomic LogP (AlogP) 2.18
H-Bond Acceptor 5
H-Bond Donor 1
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R,9R,13bS)-2,11,12-trimethoxy-7-oxido-2,6,8,9-tetrahydro-1H-indolo[7a,1-a]isoquinolin-7-ium-9-ol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7027 70.27%
Caco-2 + 0.7263 72.63%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability + 0.5714 57.14%
Subcellular localzation Mitochondria 0.4099 40.99%
OATP2B1 inhibitior - 0.8569 85.69%
OATP1B1 inhibitior + 0.8923 89.23%
OATP1B3 inhibitior + 0.9411 94.11%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.5750 57.50%
BSEP inhibitior + 0.6319 63.19%
P-glycoprotein inhibitior - 0.7001 70.01%
P-glycoprotein substrate - 0.5426 54.26%
CYP3A4 substrate + 0.6177 61.77%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.7426 74.26%
CYP3A4 inhibition - 0.9011 90.11%
CYP2C9 inhibition - 0.8118 81.18%
CYP2C19 inhibition - 0.7089 70.89%
CYP2D6 inhibition - 0.7665 76.65%
CYP1A2 inhibition - 0.7983 79.83%
CYP2C8 inhibition + 0.5555 55.55%
CYP inhibitory promiscuity - 0.9109 91.09%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.8500 85.00%
Carcinogenicity (trinary) Non-required 0.4402 44.02%
Eye corrosion - 0.9803 98.03%
Eye irritation - 0.9012 90.12%
Skin irritation - 0.7613 76.13%
Skin corrosion - 0.9209 92.09%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4160 41.60%
Micronuclear + 0.5600 56.00%
Hepatotoxicity + 0.6125 61.25%
skin sensitisation - 0.8234 82.34%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.9125 91.25%
Nephrotoxicity - 0.7765 77.65%
Acute Oral Toxicity (c) III 0.5680 56.80%
Estrogen receptor binding + 0.7871 78.71%
Androgen receptor binding + 0.5843 58.43%
Thyroid receptor binding + 0.8124 81.24%
Glucocorticoid receptor binding + 0.6467 64.67%
Aromatase binding + 0.5509 55.09%
PPAR gamma - 0.6098 60.98%
Honey bee toxicity - 0.8292 82.92%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5249 52.49%
Fish aquatic toxicity + 0.8462 84.62%

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
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.19% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.99% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.86% 94.45%
CHEMBL241 Q14432 Phosphodiesterase 3A 91.14% 92.94%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.84% 86.33%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 85.82% 89.62%
CHEMBL4208 P20618 Proteasome component C5 84.16% 90.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.96% 95.89%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 83.54% 85.14%
CHEMBL3060 Q9Y345 Glycine transporter 2 83.51% 99.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 82.55% 95.56%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 80.15% 91.03%

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.
Erythrina americana

Cross-Links

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PubChem 11152146
LOTUS LTS0010021
wikiData Q104375888