methyl (1R,2R,4S)-4-[5-[5-[[(2R,6S)-3-amino-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-4-hydroxy-6-methyloxan-2-yl]oxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
| Internal ID | 1b5387e1-407a-40da-a93d-ecd5f55aab88 |
| Taxonomy | Phenylpropanoids and polyketides > Anthracyclines |
| IUPAC Name | methyl (1R,2R,4S)-4-[5-[5-[[(2R,6S)-3-amino-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-4-hydroxy-6-methyloxan-2-yl]oxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate |
| SMILES (Canonical) | CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C=CC(=C4C3=O)O)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7C(=CC(=O)C(O7)C)N)O)N(C)C)O |
| SMILES (Isomeric) | CC[C@]1(C[C@@H](C2=C(C3=C(C=C2[C@H]1C(=O)OC)C(=O)C4=C(C=CC(=C4C3=O)O)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)O[C@H]7C(=CC(=O)[C@@H](O7)C)N)O)N(C)C)O |
| InChI | InChI=1S/C42H52N2O16/c1-8-42(53)15-27(30-19(34(42)40(52)54-7)11-20-31(36(30)50)37(51)33-24(46)10-9-23(45)32(33)35(20)49)58-28-13-22(44(5)6)38(17(3)55-28)59-29-14-26(48)39(18(4)56-29)60-41-21(43)12-25(47)16(2)57-41/h9-12,16-18,22,26-29,34,38-39,41,45-46,48,50,53H,8,13-15,43H2,1-7H3/t16-,17?,18?,22?,26?,27-,28?,29?,34-,38?,39?,41-,42+/m0/s1 |
| InChI Key | GFEWKUPUJDGEKH-YAYISERDSA-N |
| Popularity | 3 references in papers |
| Molecular Formula | C42H52N2O16 |
| Molecular Weight | 840.90 g/mol |
| Exact Mass | 840.33168358 g/mol |
| Topological Polar Surface Area (TPSA) | 263.00 Ų |
| XlogP | 3.00 |
| Atomic LogP (AlogP) | 1.93 |
| H-Bond Acceptor | 18 |
| H-Bond Donor | 6 |
| Rotatable Bonds | 9 |
| methyl (1R,2R,4S)-4-[5-[5-[[(2R,6S)-3-amino-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-4-hydroxy-6-methyloxan-2-yl]oxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate |
| NSC293858 |
| 1-Naphthacenecarboxylic acid,6-dihydro-6-methyl-5-oxo-2H-pyran-2-yl)-2,6-dideoxy-.alpha.-L-lyxo-hexopyranosyl]-2,3,6-trideoxy-3-[dimethylamino]-.alpha.-L-lyxo-hexopyranosyl]oxy]-2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7,10-tetrahydroxy-6,11-dioxo-, methyl ester, (1R-(1.alpha.,2.beta.,4.beta.(2R*,6S*)))- |
![2D Structure of methyl (1R,2R,4S)-4-[5-[5-[[(2R,6S)-3-amino-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-4-hydroxy-6-methyloxan-2-yl]oxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate](https://plantaedb.com/storage/docs/compounds/2023/11/98962e90-7e83-11ee-a5cd-6b5e8766c990.jpg "2D Structure of methyl (1R,2R,4S)-4-[5-[5-[[(2R,6S)-3-amino-6-methyl-5-oxo-2H-pyran-2-yl]oxy]-4-hydroxy-6-methyloxan-2-yl]oxy-4-(dimethylamino)-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.8670 | 86.70% |
| Caco-2 | - | 0.8651 | 86.51% |
| Blood Brain Barrier | - | 0.8250 | 82.50% |
| Human oral bioavailability | - | 0.6143 | 61.43% |
| Subcellular localzation | Lysosomes | 0.4845 | 48.45% |
| OATP2B1 inhibitior | - | 0.7171 | 71.71% |
| OATP1B1 inhibitior | + | 0.8828 | 88.28% |
| OATP1B3 inhibitior | + | 0.9461 | 94.61% |
| MATE1 inhibitior | - | 0.9800 | 98.00% |
| OCT2 inhibitior | - | 0.8250 | 82.50% |
| BSEP inhibitior | + | 0.7070 | 70.70% |
| P-glycoprotein inhibitior | + | 0.7503 | 75.03% |
| P-glycoprotein substrate | + | 0.8687 | 86.87% |
| CYP3A4 substrate | + | 0.7288 | 72.88% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8603 | 86.03% |
| CYP3A4 inhibition | - | 0.7523 | 75.23% |
| CYP2C9 inhibition | - | 0.8328 | 83.28% |
| CYP2C19 inhibition | - | 0.8081 | 80.81% |
| CYP2D6 inhibition | - | 0.8239 | 82.39% |
| CYP1A2 inhibition | - | 0.6586 | 65.86% |
| CYP2C8 inhibition | + | 0.5187 | 51.87% |
| CYP inhibitory promiscuity | - | 0.7626 | 76.26% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 0.9400 | 94.00% |
| Carcinogenicity (trinary) | Non-required | 0.4999 | 49.99% |
| Eye corrosion | - | 0.9863 | 98.63% |
| Eye irritation | - | 0.9070 | 90.70% |
| Skin irritation | - | 0.7819 | 78.19% |
| Skin corrosion | - | 0.9243 | 92.43% |
| Ames mutagenesis | + | 0.9300 | 93.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5000 | 50.00% |
| Micronuclear | + | 0.7200 | 72.00% |
| Hepatotoxicity | + | 0.6722 | 67.22% |
| skin sensitisation | - | 0.8581 | 85.81% |
| Respiratory toxicity | + | 0.9111 | 91.11% |
| Reproductive toxicity | + | 0.9111 | 91.11% |
| Mitochondrial toxicity | + | 0.9375 | 93.75% |
| Nephrotoxicity | - | 0.8383 | 83.83% |
| Acute Oral Toxicity (c) | III | 0.4769 | 47.69% |
| Estrogen receptor binding | + | 0.8673 | 86.73% |
| Androgen receptor binding | + | 0.8257 | 82.57% |
| Thyroid receptor binding | + | 0.5727 | 57.27% |
| Glucocorticoid receptor binding | + | 0.8553 | 85.53% |
| Aromatase binding | + | 0.8091 | 80.91% |
| PPAR gamma | + | 0.8189 | 81.89% |
| Honey bee toxicity | - | 0.6619 | 66.19% |
| Biodegradation | - | 0.8500 | 85.00% |
| Crustacea aquatic toxicity | - | 0.5700 | 57.00% |
| Fish aquatic toxicity | + | 0.9530 | 95.30% |
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 |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 99.87% | 91.11% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 98.39% | 96.09% |
| CHEMBL226 | P30542 | Adenosine A1 receptor | 97.78% | 95.93% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 96.98% | 89.00% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 96.88% | 97.09% |
| CHEMBL2581 | P07339 | Cathepsin D | 96.64% | 98.95% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 92.94% | 95.89% |
| CHEMBL5845 | P23415 | Glycine receptor subunit alpha-1 | 92.18% | 90.71% |
| CHEMBL3864 | Q06124 | Protein-tyrosine phosphatase 2C | 91.72% | 94.42% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 91.04% | 85.14% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 90.48% | 90.00% |
| CHEMBL4685 | P14902 | Indoleamine 2,3-dioxygenase | 90.27% | 96.38% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 89.97% | 95.56% |
| CHEMBL3880 | P07900 | Heat shock protein HSP 90-alpha | 89.89% | 96.21% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 89.59% | 94.45% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 87.81% | 91.19% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 87.78% | 86.33% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 86.35% | 100.00% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 85.91% | 94.00% |
| CHEMBL241 | Q14432 | Phosphodiesterase 3A | 85.61% | 92.94% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 83.75% | 99.23% |
| CHEMBL3922 | P50579 | Methionine aminopeptidase 2 | 83.32% | 97.28% |
| CHEMBL2378 | P30307 | Dual specificity phosphatase Cdc25C | 83.25% | 96.67% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 83.10% | 99.17% |
| CHEMBL1907605 | P24864 | Cyclin-dependent kinase 2/cyclin E1 | 82.18% | 92.88% |
| CHEMBL2373 | P21730 | C5a anaphylatoxin chemotactic receptor | 81.73% | 92.62% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 81.49% | 99.15% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 80.24% | 94.73% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 80.23% | 96.00% |
| CHEMBL2345 | P51812 | Ribosomal protein S6 kinase alpha 3 | 80.22% | 95.64% |
| CHEMBL3004 | P33527 | Multidrug resistance-associated protein 1 | 80.09% | 96.37% |
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 | 325320 |
| LOTUS | LTS0232500 |
| wikiData | Q105106494 |