13-Methoxy-6-methyl-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione

Details

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Internal ID 12c78ea1-56fb-4a3f-ae6a-0cf544db88d9
Taxonomy Alkaloids and derivatives > Indolonaphthyridine alkaloids
IUPAC Name 13-methoxy-6-methyl-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione
SMILES (Canonical) CN1C=CC2=C3C1=CC(=O)C(=O)N3C4=C2C=CC(=C4)OC
SMILES (Isomeric) CN1C=CC2=C3C1=CC(=O)C(=O)N3C4=C2C=CC(=C4)OC
InChI InChI=1S/C16H12N2O3/c1-17-6-5-11-10-4-3-9(21-2)7-12(10)18-15(11)13(17)8-14(19)16(18)20/h3-8H,1-2H3
InChI Key OXLYRYAVJWCSDD-UHFFFAOYSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C16H12N2O3
Molecular Weight 280.28 g/mol
Exact Mass 280.08479225 g/mol
Topological Polar Surface Area (TPSA) 51.50 Ų
XlogP 2.00
Atomic LogP (AlogP) 1.70
H-Bond Acceptor 5
H-Bond Donor 0
Rotatable Bonds 1

Synonyms

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Eurycomine E
BDBM50067496

2D Structure

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2D Structure of 13-Methoxy-6-methyl-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-4,7,9(16),10(15),11,13-hexaene-2,3-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9715 97.15%
Caco-2 + 0.9072 90.72%
Blood Brain Barrier + 0.8500 85.00%
Human oral bioavailability + 0.8143 81.43%
Subcellular localzation Mitochondria 0.8435 84.35%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9439 94.39%
OATP1B3 inhibitior + 0.9476 94.76%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9348 93.48%
BSEP inhibitior + 0.6895 68.95%
P-glycoprotein inhibitior - 0.7395 73.95%
P-glycoprotein substrate - 0.7565 75.65%
CYP3A4 substrate + 0.5614 56.14%
CYP2C9 substrate - 0.7698 76.98%
CYP2D6 substrate - 0.8443 84.43%
CYP3A4 inhibition - 0.6873 68.73%
CYP2C9 inhibition - 0.6941 69.41%
CYP2C19 inhibition + 0.5206 52.06%
CYP2D6 inhibition - 0.8665 86.65%
CYP1A2 inhibition + 0.8037 80.37%
CYP2C8 inhibition - 0.7648 76.48%
CYP inhibitory promiscuity + 0.6683 66.83%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.4982 49.82%
Eye corrosion - 0.9919 99.19%
Eye irritation - 0.7876 78.76%
Skin irritation - 0.8626 86.26%
Skin corrosion - 0.9650 96.50%
Ames mutagenesis + 0.6400 64.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5701 57.01%
Micronuclear + 0.7900 79.00%
Hepatotoxicity + 0.5994 59.94%
skin sensitisation - 0.9430 94.30%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity - 0.5655 56.55%
Acute Oral Toxicity (c) III 0.7228 72.28%
Estrogen receptor binding + 0.8795 87.95%
Androgen receptor binding + 0.8385 83.85%
Thyroid receptor binding + 0.6487 64.87%
Glucocorticoid receptor binding + 0.9191 91.91%
Aromatase binding + 0.6195 61.95%
PPAR gamma - 0.4930 49.30%
Honey bee toxicity - 0.8802 88.02%
Biodegradation - 0.9500 95.00%
Crustacea aquatic toxicity + 0.6200 62.00%
Fish aquatic toxicity - 0.4615 46.15%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 19180 nM
IC50
PMID: 25819098

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.10% 95.56%
CHEMBL2581 P07339 Cathepsin D 94.45% 98.95%
CHEMBL5697 Q9GZT9 Egl nine homolog 1 94.36% 93.40%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.26% 96.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 92.88% 94.00%
CHEMBL4208 P20618 Proteasome component C5 91.32% 90.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 90.72% 93.99%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 88.68% 99.15%
CHEMBL235 P37231 Peroxisome proliferator-activated receptor gamma 88.30% 95.39%
CHEMBL1293249 Q13887 Kruppel-like factor 5 87.63% 86.33%
CHEMBL255 P29275 Adenosine A2b receptor 87.19% 98.59%
CHEMBL3864 Q06124 Protein-tyrosine phosphatase 2C 85.27% 94.42%
CHEMBL2095172 P14867 GABA-A receptor; alpha-1/beta-2/gamma-2 83.85% 92.67%
CHEMBL2085 P14174 Macrophage migration inhibitory factor 83.20% 80.78%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.07% 96.00%
CHEMBL1907 P15144 Aminopeptidase N 81.98% 93.31%
CHEMBL2146302 O94925 Glutaminase kidney isoform, mitochondrial 81.62% 100.00%
CHEMBL2535 P11166 Glucose transporter 81.44% 98.75%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 80.73% 85.14%
CHEMBL3714130 P46095 G-protein coupled receptor 6 80.72% 97.36%

Cross-Links

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PubChem 10912909
NPASS NPC295898
ChEMBL CHEMBL3400666
LOTUS LTS0199958
wikiData Q105202775