(9S)-7-[(2R,4S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,6,9,11-tetrahydroxy-9-(1-hydroxyethyl)-8,10-dihydro-7H-tetracene-5,12-dione
| Internal ID | 32deaca0-e0d3-4ac4-8cb0-de513bb97a9d |
| Taxonomy | Phenylpropanoids and polyketides > Anthracyclines |
| IUPAC Name | (9S)-7-[(2R,4S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,6,9,11-tetrahydroxy-9-(1-hydroxyethyl)-8,10-dihydro-7H-tetracene-5,12-dione |
| SMILES (Canonical) | |
| SMILES (Isomeric) | |
| InChI | InChI=1S/C40H51NO15/c1-16-23(43)10-11-27(51-16)55-39-18(3)53-29(13-25(39)45)56-38-17(2)52-28(12-22(38)41(5)6)54-26-15-40(50,19(4)42)14-21-31(26)37(49)33-32(35(21)47)34(46)20-8-7-9-24(44)30(20)36(33)48/h7-9,16-19,22,25-29,38-39,42,44-45,47,49-50H,10-15H2,1-6H3/t16-,17-,18-,19?,22-,25-,26?,27-,28-,29-,38?,39+,40-/m0/s1 |
| InChI Key | RFRIIINGCQOYCL-QCPFSNFXSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C40H51NO15 |
| Molecular Weight | 785.80 g/mol |
| Exact Mass | 785.32586992 g/mol |
| Topological Polar Surface Area (TPSA) | 231.00 Ų |
| XlogP | 2.70 |
| Atomic LogP (AlogP) | 2.12 |
| H-Bond Acceptor | 16 |
| H-Bond Donor | 6 |
| Rotatable Bonds | 8 |
| 80470-08-2 |
| (9S)-7-[(2R,4S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,6,9,11-tetrahydroxy-9-(1-hydroxyethyl)-8,10-dihydro-7H-tetracene-5,12-dione |
| DTXSID301001266 |
| 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-8-(1-hydroxyethyl)-10-((2,3,6-trideoxy-4-O-(2,6-dideoxy-4-O-((2R-trans)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)- |
| 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-8-(1-hydroxyethyl)-1,6,8,11-tetrahydroxy-10-((2,3,6-trideoxy-4-O-(2,6-dideoxy-4-O-((2R-trans)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)- |
| 3,5,10,12-Tetrahydroxy-3-(1-hydroxyethyl)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,3,6-trideoxy-4-O-[2,6-dideoxy-4-O-(6-methyl-5-oxooxan-2-yl)hexopyranosyl]-3-(dimethylamino)hexopyranoside |
![2D Structure of (9S)-7-[(2R,4S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,6,9,11-tetrahydroxy-9-(1-hydroxyethyl)-8,10-dihydro-7H-tetracene-5,12-dione](https://plantaedb.com/storage/docs/compounds/2023/11/trisarubicinol.jpg "2D Structure of (9S)-7-[(2R,4S,6S)-4-(dimethylamino)-5-[(2S,4S,5S,6S)-4-hydroxy-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-4,6,9,11-tetrahydroxy-9-(1-hydroxyethyl)-8,10-dihydro-7H-tetracene-5,12-dione")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.6198 | 61.98% |
| Caco-2 | - | 0.8708 | 87.08% |
| Blood Brain Barrier | - | 0.9750 | 97.50% |
| Human oral bioavailability | - | 0.7143 | 71.43% |
| Subcellular localzation | Mitochondria | 0.4141 | 41.41% |
| OATP2B1 inhibitior | - | 0.8586 | 85.86% |
| OATP1B1 inhibitior | + | 0.8622 | 86.22% |
| OATP1B3 inhibitior | + | 0.9343 | 93.43% |
| MATE1 inhibitior | - | 1.0000 | 100.00% |
| OCT2 inhibitior | + | 0.5429 | 54.29% |
| BSEP inhibitior | + | 0.8466 | 84.66% |
| P-glycoprotein inhibitior | + | 0.7374 | 73.74% |
| P-glycoprotein substrate | + | 0.8748 | 87.48% |
| CYP3A4 substrate | + | 0.7318 | 73.18% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8190 | 81.90% |
| CYP3A4 inhibition | - | 0.8561 | 85.61% |
| CYP2C9 inhibition | - | 0.8835 | 88.35% |
| CYP2C19 inhibition | - | 0.8673 | 86.73% |
| CYP2D6 inhibition | - | 0.8680 | 86.80% |
| CYP1A2 inhibition | - | 0.5195 | 51.95% |
| CYP2C8 inhibition | - | 0.6244 | 62.44% |
| CYP inhibitory promiscuity | - | 0.9733 | 97.33% |
| UGT catelyzed | - | 0.5000 | 50.00% |
| Carcinogenicity (binary) | - | 0.9600 | 96.00% |
| Carcinogenicity (trinary) | Non-required | 0.5598 | 55.98% |
| Eye corrosion | - | 0.9888 | 98.88% |
| Eye irritation | - | 0.9109 | 91.09% |
| Skin irritation | - | 0.7890 | 78.90% |
| Skin corrosion | - | 0.9313 | 93.13% |
| Ames mutagenesis | + | 0.8446 | 84.46% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4694 | 46.94% |
| Micronuclear | + | 0.6300 | 63.00% |
| Hepatotoxicity | + | 0.5625 | 56.25% |
| skin sensitisation | - | 0.8858 | 88.58% |
| Respiratory toxicity | + | 0.9444 | 94.44% |
| Reproductive toxicity | + | 0.9000 | 90.00% |
| Mitochondrial toxicity | + | 0.9250 | 92.50% |
| Nephrotoxicity | - | 0.7525 | 75.25% |
| Acute Oral Toxicity (c) | II | 0.5545 | 55.45% |
| Estrogen receptor binding | + | 0.8780 | 87.80% |
| Androgen receptor binding | + | 0.7700 | 77.00% |
| Thyroid receptor binding | - | 0.5098 | 50.98% |
| Glucocorticoid receptor binding | + | 0.8440 | 84.40% |
| Aromatase binding | + | 0.8049 | 80.49% |
| PPAR gamma | + | 0.7985 | 79.85% |
| Honey bee toxicity | - | 0.6610 | 66.10% |
| Biodegradation | - | 0.7250 | 72.50% |
| Crustacea aquatic toxicity | - | 0.6700 | 67.00% |
| Fish aquatic toxicity | + | 0.8627 | 86.27% |
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 | 99.71% | 91.11% |
| CHEMBL2581 | P07339 | Cathepsin D | 99.36% | 98.95% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 97.94% | 89.00% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 97.38% | 96.09% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 96.36% | 95.56% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 96.28% | 97.09% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 96.12% | 99.23% |
| CHEMBL4685 | P14902 | Indoleamine 2,3-dioxygenase | 95.86% | 96.38% |
| CHEMBL3475 | P05121 | Plasminogen activator inhibitor-1 | 93.02% | 83.00% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 92.76% | 99.15% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 91.67% | 85.14% |
| CHEMBL1907605 | P24864 | Cyclin-dependent kinase 2/cyclin E1 | 90.08% | 92.88% |
| CHEMBL3359 | P21462 | Formyl peptide receptor 1 | 89.94% | 93.56% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 89.68% | 95.89% |
| CHEMBL3880 | P07900 | Heat shock protein HSP 90-alpha | 89.11% | 96.21% |
| CHEMBL4303 | P08238 | Heat shock protein HSP 90-beta | 87.58% | 96.77% |
| CHEMBL1937 | Q92769 | Histone deacetylase 2 | 87.34% | 94.75% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 87.29% | 100.00% |
| CHEMBL4478 | Q00975 | Voltage-gated N-type calcium channel alpha-1B subunit | 86.87% | 97.14% |
| CHEMBL1907600 | Q00535 | Cyclin-dependent kinase 5/CDK5 activator 1 | 86.78% | 93.03% |
| CHEMBL226 | P30542 | Adenosine A1 receptor | 86.06% | 95.93% |
| CHEMBL2378 | P30307 | Dual specificity phosphatase Cdc25C | 85.92% | 96.67% |
| CHEMBL3145 | P42338 | PI3-kinase p110-beta subunit | 84.41% | 98.75% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 82.81% | 94.00% |
| CHEMBL2094135 | Q96BI3 | Gamma-secretase | 82.04% | 98.05% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 81.53% | 91.19% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 81.34% | 97.25% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 80.93% | 90.00% |
| CHEMBL2373 | P21730 | C5a anaphylatoxin chemotactic receptor | 80.57% | 92.62% |
| CHEMBL2553 | Q15418 | Ribosomal protein S6 kinase alpha 1 | 80.42% | 85.11% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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| PubChem | 157427 |
| LOTUS | LTS0239518 |
| wikiData | Q104958443 |