2,3,4,9,10-pentamethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline

Details

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Internal ID 1d675bd1-6d5e-4c14-a027-5752438ce70b
Taxonomy Alkaloids and derivatives > Protoberberine alkaloids and derivatives
IUPAC Name 2,3,4,9,10-pentamethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
SMILES (Canonical) COC1=C(C2=C(CC3C4=CC(=C(C(=C4CCN3C2)OC)OC)OC)C=C1)OC
SMILES (Isomeric) COC1=C(C2=C(CC3C4=CC(=C(C(=C4CCN3C2)OC)OC)OC)C=C1)OC
InChI InChI=1S/C22H27NO5/c1-24-18-7-6-13-10-17-15-11-19(25-2)22(28-5)21(27-4)14(15)8-9-23(17)12-16(13)20(18)26-3/h6-7,11,17H,8-10,12H2,1-5H3
InChI Key ODXIINJWIDRSBL-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C22H27NO5
Molecular Weight 385.50 g/mol
Exact Mass 385.18892296 g/mol
Topological Polar Surface Area (TPSA) 49.40 Ų
XlogP 3.20
Atomic LogP (AlogP) 3.39
H-Bond Acceptor 6
H-Bond Donor 0
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 2,3,4,9,10-pentamethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9392 93.92%
Caco-2 + 0.8988 89.88%
Blood Brain Barrier + 0.7000 70.00%
Human oral bioavailability - 0.7286 72.86%
Subcellular localzation Mitochondria 0.6651 66.51%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9358 93.58%
OATP1B3 inhibitior + 0.9456 94.56%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior + 0.5500 55.00%
BSEP inhibitior - 0.4909 49.09%
P-glycoprotein inhibitior - 0.4873 48.73%
P-glycoprotein substrate - 0.5652 56.52%
CYP3A4 substrate + 0.5883 58.83%
CYP2C9 substrate + 0.7753 77.53%
CYP2D6 substrate + 0.8760 87.60%
CYP3A4 inhibition - 0.8034 80.34%
CYP2C9 inhibition - 0.9476 94.76%
CYP2C19 inhibition - 0.7742 77.42%
CYP2D6 inhibition + 0.5497 54.97%
CYP1A2 inhibition - 0.5995 59.95%
CYP2C8 inhibition - 0.6009 60.09%
CYP inhibitory promiscuity - 0.8359 83.59%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6200 62.00%
Eye corrosion - 0.9891 98.91%
Eye irritation - 0.9602 96.02%
Skin irritation - 0.7869 78.69%
Skin corrosion - 0.9479 94.79%
Ames mutagenesis - 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8917 89.17%
Micronuclear - 0.5700 57.00%
Hepatotoxicity - 0.5375 53.75%
skin sensitisation - 0.8946 89.46%
Respiratory toxicity + 0.8667 86.67%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity - 0.7130 71.30%
Acute Oral Toxicity (c) II 0.4852 48.52%
Estrogen receptor binding + 0.6470 64.70%
Androgen receptor binding + 0.5877 58.77%
Thyroid receptor binding + 0.6661 66.61%
Glucocorticoid receptor binding + 0.6061 60.61%
Aromatase binding - 0.7978 79.78%
PPAR gamma - 0.6221 62.21%
Honey bee toxicity - 0.8573 85.73%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity + 0.7400 74.00%
Fish aquatic toxicity - 0.4067 40.67%

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 98.38% 96.09%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 97.01% 93.40%
CHEMBL5747 Q92793 CREB-binding protein 95.87% 95.12%
CHEMBL217 P14416 Dopamine D2 receptor 95.76% 95.62%
CHEMBL4302 P08183 P-glycoprotein 1 95.06% 92.98%
CHEMBL240 Q12809 HERG 94.15% 89.76%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.38% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.99% 94.45%
CHEMBL2056 P21728 Dopamine D1 receptor 86.90% 91.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 86.87% 95.89%
CHEMBL3192 Q9BY41 Histone deacetylase 8 86.61% 93.99%
CHEMBL261 P00915 Carbonic anhydrase I 86.56% 96.76%
CHEMBL2535 P11166 Glucose transporter 86.52% 98.75%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.02% 95.56%
CHEMBL2069156 Q14145 Kelch-like ECH-associated protein 1 85.56% 82.38%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 85.41% 89.62%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 84.48% 95.89%
CHEMBL2581 P07339 Cathepsin D 84.36% 98.95%
CHEMBL3438 Q05513 Protein kinase C zeta 84.26% 88.48%
CHEMBL2146302 O94925 Glutaminase kidney isoform, mitochondrial 83.91% 100.00%
CHEMBL4208 P20618 Proteasome component C5 82.12% 90.00%
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 81.77% 89.05%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.73% 85.14%

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.
Parabaena sagittata

Cross-Links

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PubChem 14487605
LOTUS LTS0129446
wikiData Q105190082