2,3,9-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-1,10-diol

Details

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Internal ID f2c5893b-0bea-4675-8a8b-3a5ff797415a
Taxonomy Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name 2,3,9-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-1,10-diol
SMILES (Canonical) COC1=C(C(=C2C3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O)OC
SMILES (Isomeric) COC1=C(C(=C2C3CC4=C(CN3CCC2=C1)C(=C(C=C4)O)OC)O)OC
InChI InChI=1S/C20H23NO5/c1-24-16-9-12-6-7-21-10-13-11(4-5-15(22)19(13)25-2)8-14(21)17(12)18(23)20(16)26-3/h4-5,9,14,22-23H,6-8,10H2,1-3H3
InChI Key OVJXYLKOQXXUAJ-UHFFFAOYSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C20H23NO5
Molecular Weight 357.40 g/mol
Exact Mass 357.15762283 g/mol
Topological Polar Surface Area (TPSA) 71.40 Ų
XlogP 2.60
Atomic LogP (AlogP) 2.78
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 2,3,9-trimethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline-1,10-diol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6838 68.38%
Caco-2 + 0.8526 85.26%
Blood Brain Barrier + 0.6000 60.00%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.7523 75.23%
OATP2B1 inhibitior - 0.8598 85.98%
OATP1B1 inhibitior + 0.9361 93.61%
OATP1B3 inhibitior + 0.9403 94.03%
MATE1 inhibitior - 0.8600 86.00%
OCT2 inhibitior - 0.5000 50.00%
BSEP inhibitior - 0.6995 69.95%
P-glycoprotein inhibitior - 0.7193 71.93%
P-glycoprotein substrate - 0.5522 55.22%
CYP3A4 substrate + 0.6048 60.48%
CYP2C9 substrate + 0.7825 78.25%
CYP2D6 substrate + 0.8432 84.32%
CYP3A4 inhibition - 0.8968 89.68%
CYP2C9 inhibition - 0.9377 93.77%
CYP2C19 inhibition - 0.6280 62.80%
CYP2D6 inhibition + 0.5774 57.74%
CYP1A2 inhibition + 0.6710 67.10%
CYP2C8 inhibition + 0.4644 46.44%
CYP inhibitory promiscuity - 0.8882 88.82%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6277 62.77%
Eye corrosion - 0.9897 98.97%
Eye irritation - 0.9382 93.82%
Skin irritation - 0.7763 77.63%
Skin corrosion - 0.9429 94.29%
Ames mutagenesis - 0.5000 50.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3997 39.97%
Micronuclear - 0.5000 50.00%
Hepatotoxicity - 0.6625 66.25%
skin sensitisation - 0.8895 88.95%
Respiratory toxicity + 0.8778 87.78%
Reproductive toxicity + 0.7889 78.89%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity - 0.9046 90.46%
Acute Oral Toxicity (c) II 0.4472 44.72%
Estrogen receptor binding + 0.5814 58.14%
Androgen receptor binding + 0.5318 53.18%
Thyroid receptor binding + 0.6343 63.43%
Glucocorticoid receptor binding + 0.5639 56.39%
Aromatase binding - 0.7039 70.39%
PPAR gamma - 0.5982 59.82%
Honey bee toxicity - 0.8455 84.55%
Biodegradation - 1.0000 100.00%
Crustacea aquatic toxicity + 0.6000 60.00%
Fish aquatic toxicity - 0.4320 43.20%

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
CHEMBL217 P14416 Dopamine D2 receptor 98.20% 95.62%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.95% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.78% 96.09%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 95.72% 93.40%
CHEMBL2041 P07949 Tyrosine-protein kinase receptor RET 94.17% 91.79%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.64% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.93% 86.33%
CHEMBL241 Q14432 Phosphodiesterase 3A 90.24% 92.94%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.34% 95.89%
CHEMBL2535 P11166 Glucose transporter 88.89% 98.75%
CHEMBL3438 Q05513 Protein kinase C zeta 88.89% 88.48%
CHEMBL2056 P21728 Dopamine D1 receptor 88.75% 91.00%
CHEMBL5469 Q14289 Protein tyrosine kinase 2 beta 88.49% 91.03%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 87.71% 94.45%
CHEMBL4208 P20618 Proteasome component C5 87.50% 90.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 86.17% 93.99%
CHEMBL5747 Q92793 CREB-binding protein 86.01% 95.12%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 84.82% 82.38%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 84.42% 89.62%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.60% 94.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.33% 90.71%
CHEMBL3060 Q9Y345 Glycine transporter 2 82.47% 99.17%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 81.48% 99.15%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.87% 85.14%
CHEMBL2146302 O94925 Glutaminase kidney isoform, mitochondrial 80.86% 100.00%
CHEMBL2581 P07339 Cathepsin D 80.84% 98.95%

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.
Corydalis pallida
Stephania suberosa

Cross-Links

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PubChem 5315668
NPASS NPC31326
LOTUS LTS0013775
wikiData Q104394108