(2S)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid
| Internal ID | 65705704-ef2e-4937-a888-0b0a8bd7f6f8 |
| Taxonomy | Alkaloids and derivatives > Camptothecins |
| IUPAC Name | (2S)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid |
| SMILES (Canonical) | CCC1=C2CN3C(=CC(=C(C3=O)CO)C(CC)(C(=O)O)O)C2=NC4=C1C=C(C=C4)O |
| SMILES (Isomeric) | CCC1=C2CN3C(=CC(=C(C3=O)CO)[C@@](CC)(C(=O)O)O)C2=NC4=C1C=C(C=C4)O |
| InChI | InChI=1S/C22H22N2O6/c1-3-12-13-7-11(26)5-6-17(13)23-19-14(12)9-24-18(19)8-16(15(10-25)20(24)27)22(30,4-2)21(28)29/h5-8,25-26,30H,3-4,9-10H2,1-2H3,(H,28,29)/t22-/m0/s1 |
| InChI Key | IRKZFHZUIBLGKU-QFIPXVFZSA-N |
| Popularity | 2 references in papers |
| Molecular Formula | C22H22N2O6 |
| Molecular Weight | 410.40 g/mol |
| Exact Mass | 410.14778643 g/mol |
| Topological Polar Surface Area (TPSA) | 131.00 Ų |
| XlogP | 1.20 |
| Atomic LogP (AlogP) | 1.87 |
| H-Bond Acceptor | 7 |
| H-Bond Donor | 4 |
| Rotatable Bonds | 5 |
| CHEMBL2074578 |
| SN-38C |
| SN-38 carboxylic acid |
| CHEBI:149481 |
| BDBM50485568 |
| (2S)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid |
| CS-0164104 |
| (2S)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-9,11-dihydroindolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid |
| (S)-2-(12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-9,11-dihydroindolizino[1,2-b]quinolin-7-yl)-2-hydroxybutanoic acid? (Irinotecan Impurity pound(c) |
![2D Structure of (2S)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid](https://plantaedb.com/storage/docs/compounds/2023/11/3a63ad00-877c-11ee-86ae-f13b26fafec5.jpg "2D Structure of (2S)-2-[12-ethyl-2-hydroxy-8-(hydroxymethyl)-9-oxo-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoic acid")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.8284 | 82.84% |
| Caco-2 | - | 0.9039 | 90.39% |
| Blood Brain Barrier | - | 0.6750 | 67.50% |
| Human oral bioavailability | - | 0.6571 | 65.71% |
| Subcellular localzation | Mitochondria | 0.5612 | 56.12% |
| OATP2B1 inhibitior | + | 0.5793 | 57.93% |
| OATP1B1 inhibitior | + | 0.8587 | 85.87% |
| OATP1B3 inhibitior | + | 0.9328 | 93.28% |
| MATE1 inhibitior | - | 0.8200 | 82.00% |
| OCT2 inhibitior | - | 0.9750 | 97.50% |
| BSEP inhibitior | + | 0.8367 | 83.67% |
| P-glycoprotein inhibitior | - | 0.8028 | 80.28% |
| P-glycoprotein substrate | - | 0.5491 | 54.91% |
| CYP3A4 substrate | + | 0.6277 | 62.77% |
| CYP2C9 substrate | - | 0.8012 | 80.12% |
| CYP2D6 substrate | - | 0.8893 | 88.93% |
| CYP3A4 inhibition | + | 0.5899 | 58.99% |
| CYP2C9 inhibition | - | 0.8080 | 80.80% |
| CYP2C19 inhibition | - | 0.8169 | 81.69% |
| CYP2D6 inhibition | - | 0.8829 | 88.29% |
| CYP1A2 inhibition | + | 0.7491 | 74.91% |
| CYP2C8 inhibition | + | 0.5346 | 53.46% |
| CYP inhibitory promiscuity | - | 0.7144 | 71.44% |
| UGT catelyzed | - | 0.5000 | 50.00% |
| Carcinogenicity (binary) | - | 0.8400 | 84.00% |
| Carcinogenicity (trinary) | Non-required | 0.5430 | 54.30% |
| Eye corrosion | - | 0.9900 | 99.00% |
| Eye irritation | - | 0.9125 | 91.25% |
| Skin irritation | - | 0.8006 | 80.06% |
| Skin corrosion | - | 0.9410 | 94.10% |
| Ames mutagenesis | + | 0.5446 | 54.46% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5527 | 55.27% |
| Micronuclear | + | 0.7700 | 77.00% |
| Hepatotoxicity | + | 0.5500 | 55.00% |
| skin sensitisation | - | 0.8826 | 88.26% |
| Respiratory toxicity | + | 0.7889 | 78.89% |
| Reproductive toxicity | + | 0.9333 | 93.33% |
| Mitochondrial toxicity | + | 0.9125 | 91.25% |
| Nephrotoxicity | - | 0.6977 | 69.77% |
| Acute Oral Toxicity (c) | III | 0.4400 | 44.00% |
| Estrogen receptor binding | + | 0.8399 | 83.99% |
| Androgen receptor binding | + | 0.8004 | 80.04% |
| Thyroid receptor binding | + | 0.5854 | 58.54% |
| Glucocorticoid receptor binding | + | 0.8402 | 84.02% |
| Aromatase binding | + | 0.7683 | 76.83% |
| PPAR gamma | + | 0.6972 | 69.72% |
| Honey bee toxicity | - | 0.9232 | 92.32% |
| Biodegradation | - | 0.8500 | 85.00% |
| Crustacea aquatic toxicity | - | 0.6700 | 67.00% |
| Fish aquatic toxicity | + | 0.8589 | 85.89% |
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 |
|---|---|---|---|---|
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 99.09% | 85.14% |
| CHEMBL2581 | P07339 | Cathepsin D | 98.55% | 98.95% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 95.66% | 86.33% |
| CHEMBL1781 | P11387 | DNA topoisomerase I | 95.25% | 97.00% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 93.74% | 96.09% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 89.47% | 95.56% |
| CHEMBL202 | P00374 | Dihydrofolate reductase | 88.85% | 89.92% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 88.44% | 89.00% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 87.57% | 91.11% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 87.48% | 99.23% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 86.10% | 94.00% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 83.65% | 99.17% |
| CHEMBL4829 | O00763 | Acetyl-CoA carboxylase 2 | 82.01% | 98.00% |
| CHEMBL4040 | P28482 | MAP kinase ERK2 | 81.11% | 83.82% |
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.
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| There are no matching plants. |
| PubChem | 443149 |
| LOTUS | LTS0095215 |
| wikiData | Q105118928 |