Metatacarboline A
| Internal ID | 0c1b4dbf-3c47-4daf-a72b-d5233a664ba4 |
| Taxonomy | Alkaloids and derivatives > Harmala alkaloids |
| IUPAC Name | 1-[3-[(2S)-2-carboxypyrrolidin-1-yl]-3-oxopropyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid |
| SMILES (Canonical) | C1CC(N(C1)C(=O)CCC2=C3C(=CC(=N2)C(=O)O)C4=CC=CC=C4N3)C(=O)O |
| SMILES (Isomeric) | C1C[C@H](N(C1)C(=O)CCC2=C3C(=CC(=N2)C(=O)O)C4=CC=CC=C4N3)C(=O)O |
| InChI | InChI=1S/C20H19N3O5/c24-17(23-9-3-6-16(23)20(27)28)8-7-14-18-12(10-15(21-14)19(25)26)11-4-1-2-5-13(11)22-18/h1-2,4-5,10,16,22H,3,6-9H2,(H,25,26)(H,27,28)/t16-/m0/s1 |
| InChI Key | VSQKKTIEHWELDM-INIZCTEOSA-N |
| Popularity | 2 references in papers |
| Molecular Formula | C20H19N3O5 |
| Molecular Weight | 381.40 g/mol |
| Exact Mass | 381.13247072 g/mol |
| Topological Polar Surface Area (TPSA) | 124.00 Ų |
| XlogP | 2.00 |
| Atomic LogP (AlogP) | 2.42 |
| H-Bond Acceptor | 4 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 5 |
| 1-[3-[(2S)-2-carboxypyrrolidin-1-yl]-3-oxopropyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid |
| 1-(3-((2S)-2-carboxypyrrolidin-1-yl)-3-oxopropyl)-9H-pyrido(3,4-b)indole-3-carboxylic acid |
| RefChem:156811 |
| CHEMBL3786550 |
| CHEBI:215285 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.6608 | 66.08% |
| Caco-2 | - | 0.9202 | 92.02% |
| Blood Brain Barrier | - | 0.6250 | 62.50% |
| Human oral bioavailability | + | 0.5714 | 57.14% |
| Subcellular localzation | Mitochondria | 0.8998 | 89.98% |
| OATP2B1 inhibitior | - | 0.7162 | 71.62% |
| OATP1B1 inhibitior | + | 0.8864 | 88.64% |
| OATP1B3 inhibitior | + | 0.9363 | 93.63% |
| MATE1 inhibitior | - | 0.9000 | 90.00% |
| OCT2 inhibitior | - | 0.7862 | 78.62% |
| BSEP inhibitior | + | 0.8788 | 87.88% |
| P-glycoprotein inhibitior | - | 0.6877 | 68.77% |
| P-glycoprotein substrate | - | 0.5744 | 57.44% |
| CYP3A4 substrate | + | 0.6110 | 61.10% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8417 | 84.17% |
| CYP3A4 inhibition | - | 0.9124 | 91.24% |
| CYP2C9 inhibition | - | 0.8048 | 80.48% |
| CYP2C19 inhibition | - | 0.8232 | 82.32% |
| CYP2D6 inhibition | - | 0.9760 | 97.60% |
| CYP1A2 inhibition | - | 0.9569 | 95.69% |
| CYP2C8 inhibition | + | 0.5147 | 51.47% |
| CYP inhibitory promiscuity | - | 0.7330 | 73.30% |
| UGT catelyzed | - | 0.0000 | 0.00% |
| Carcinogenicity (binary) | - | 0.9800 | 98.00% |
| Carcinogenicity (trinary) | Non-required | 0.6934 | 69.34% |
| Eye corrosion | - | 0.9947 | 99.47% |
| Eye irritation | - | 0.9822 | 98.22% |
| Skin irritation | - | 0.7985 | 79.85% |
| Skin corrosion | - | 0.9608 | 96.08% |
| Ames mutagenesis | - | 0.5000 | 50.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.6568 | 65.68% |
| Micronuclear | + | 0.7400 | 74.00% |
| Hepatotoxicity | + | 0.8125 | 81.25% |
| skin sensitisation | - | 0.9332 | 93.32% |
| Respiratory toxicity | + | 0.9111 | 91.11% |
| Reproductive toxicity | + | 0.9111 | 91.11% |
| Mitochondrial toxicity | + | 0.9000 | 90.00% |
| Nephrotoxicity | - | 0.8584 | 85.84% |
| Acute Oral Toxicity (c) | III | 0.6717 | 67.17% |
| Estrogen receptor binding | + | 0.7696 | 76.96% |
| Androgen receptor binding | + | 0.6582 | 65.82% |
| Thyroid receptor binding | - | 0.5000 | 50.00% |
| Glucocorticoid receptor binding | + | 0.5825 | 58.25% |
| Aromatase binding | + | 0.7097 | 70.97% |
| PPAR gamma | + | 0.5837 | 58.37% |
| Honey bee toxicity | - | 0.9098 | 90.98% |
| Biodegradation | - | 0.8500 | 85.00% |
| Crustacea aquatic toxicity | - | 0.6000 | 60.00% |
| Fish aquatic toxicity | + | 0.8354 | 83.54% |
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 | 95.33% | 96.09% |
| CHEMBL2581 | P07339 | Cathepsin D | 94.88% | 98.95% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 91.56% | 99.23% |
| CHEMBL213 | P08588 | Beta-1 adrenergic receptor | 90.72% | 95.56% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 89.75% | 95.56% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 86.92% | 91.11% |
| CHEMBL5203 | P33316 | dUTP pyrophosphatase | 86.56% | 99.18% |
| CHEMBL1781 | P11387 | DNA topoisomerase I | 86.12% | 97.00% |
| CHEMBL2035 | P08912 | Muscarinic acetylcholine receptor M5 | 85.15% | 94.62% |
| CHEMBL1795139 | Q8IU80 | Transmembrane protease serine 6 | 84.96% | 98.33% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 84.81% | 97.09% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 84.68% | 86.33% |
| CHEMBL3155 | P34969 | Serotonin 7 (5-HT7) receptor | 84.46% | 90.71% |
| CHEMBL3202 | P48147 | Prolyl endopeptidase | 84.12% | 90.65% |
| CHEMBL241 | Q14432 | Phosphodiesterase 3A | 83.45% | 92.94% |
| CHEMBL1944495 | P28065 | Proteasome subunit beta type-9 | 82.88% | 97.50% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 82.85% | 90.00% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 81.89% | 97.25% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 81.83% | 94.45% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 80.54% | 99.17% |
| CHEMBL2693 | Q9UIQ6 | Cystinyl aminopeptidase | 80.22% | 97.64% |
| CHEMBL1907600 | Q00535 | Cyclin-dependent kinase 5/CDK5 activator 1 | 80.11% | 93.03% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 71578886 |
| LOTUS | LTS0229628 |
| wikiData | Q77562603 |