methyl (E)-4-(4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-4-oxobut-2-enoate

Details

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Internal ID aeb8e015-d62c-483d-a789-55b4ca5f2d9f
Taxonomy Alkaloids and derivatives > Harmala alkaloids
IUPAC Name methyl (E)-4-(4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-4-oxobut-2-enoate
SMILES (Canonical) COC1=CC=CC2=C1NC3=C2C(=CN=C3C(=O)C=CC(=O)OC)OC
SMILES (Isomeric) COC1=CC=CC2=C1NC3=C2C(=CN=C3C(=O)/C=C/C(=O)OC)OC
InChI InChI=1S/C18H16N2O5/c1-23-12-6-4-5-10-15-13(24-2)9-19-17(18(15)20-16(10)12)11(21)7-8-14(22)25-3/h4-9,20H,1-3H3/b8-7+
InChI Key FISAWESAYLLNSY-BQYQJAHWSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C18H16N2O5
Molecular Weight 340.30 g/mol
Exact Mass 340.10592162 g/mol
Topological Polar Surface Area (TPSA) 90.50 Ų
XlogP 2.40
Atomic LogP (AlogP) 2.65
H-Bond Acceptor 6
H-Bond Donor 1
Rotatable Bonds 5

Synonyms

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Picrasidine E
CHEMBL3400676
(E)-4-(4,8-Dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-4-oxo-2-butenoic acid methyl ester

2D Structure

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2D Structure of methyl (E)-4-(4,8-dimethoxy-9H-pyrido[3,4-b]indol-1-yl)-4-oxobut-2-enoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9933 99.33%
Caco-2 + 0.7309 73.09%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.7416 74.16%
OATP2B1 inhibitior - 0.8523 85.23%
OATP1B1 inhibitior + 0.9405 94.05%
OATP1B3 inhibitior + 0.9182 91.82%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior + 0.6442 64.42%
P-glycoprotein inhibitior + 0.6233 62.33%
P-glycoprotein substrate - 0.5718 57.18%
CYP3A4 substrate + 0.6415 64.15%
CYP2C9 substrate - 0.5958 59.58%
CYP2D6 substrate - 0.8762 87.62%
CYP3A4 inhibition + 0.5841 58.41%
CYP2C9 inhibition - 0.8202 82.02%
CYP2C19 inhibition - 0.8189 81.89%
CYP2D6 inhibition - 0.8699 86.99%
CYP1A2 inhibition + 0.6425 64.25%
CYP2C8 inhibition + 0.7848 78.48%
CYP inhibitory promiscuity + 0.6352 63.52%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9623 96.23%
Carcinogenicity (trinary) Non-required 0.3920 39.20%
Eye corrosion - 0.9910 99.10%
Eye irritation - 0.6825 68.25%
Skin irritation - 0.8617 86.17%
Skin corrosion - 0.9689 96.89%
Ames mutagenesis + 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4235 42.35%
Micronuclear + 0.7500 75.00%
Hepatotoxicity + 0.6333 63.33%
skin sensitisation - 0.9303 93.03%
Respiratory toxicity + 0.6444 64.44%
Reproductive toxicity + 0.5667 56.67%
Mitochondrial toxicity + 0.5125 51.25%
Nephrotoxicity - 0.6547 65.47%
Acute Oral Toxicity (c) III 0.6026 60.26%
Estrogen receptor binding + 0.8693 86.93%
Androgen receptor binding + 0.6989 69.89%
Thyroid receptor binding + 0.6857 68.57%
Glucocorticoid receptor binding + 0.9407 94.07%
Aromatase binding + 0.7182 71.82%
PPAR gamma + 0.7900 79.00%
Honey bee toxicity - 0.8464 84.64%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.8270 82.70%

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 96.93% 96.09%
CHEMBL2535 P11166 Glucose transporter 96.41% 98.75%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.86% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 94.37% 85.14%
CHEMBL213 P08588 Beta-1 adrenergic receptor 90.95% 95.56%
CHEMBL2292 Q13627 Dual-specificity tyrosine-phosphorylation regulated kinase 1A 89.98% 93.24%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 89.30% 94.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 89.20% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 87.92% 99.23%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.67% 99.17%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 86.49% 96.00%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 86.47% 89.44%
CHEMBL1937 Q92769 Histone deacetylase 2 86.40% 94.75%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.38% 94.45%
CHEMBL3976 Q9UHL4 Dipeptidyl peptidase II 85.03% 92.29%
CHEMBL1255126 O15151 Protein Mdm4 83.54% 90.20%
CHEMBL1868 P17948 Vascular endothelial growth factor receptor 1 83.14% 96.47%
CHEMBL3401 O75469 Pregnane X receptor 82.28% 94.73%
CHEMBL4145 Q9UKV0 Histone deacetylase 9 82.20% 85.49%
CHEMBL3192 Q9BY41 Histone deacetylase 8 81.98% 93.99%
CHEMBL1806 P11388 DNA topoisomerase II alpha 81.07% 89.00%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.51% 95.50%

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.
Picrasma quassioides

Cross-Links

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PubChem 5320551
NPASS NPC148889
LOTUS LTS0017939
wikiData Q104995837