Aesculioside IV-23D1
| Internal ID | 49099eb0-4c10-4801-9080-13e6c8fb0b28 |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins |
| IUPAC Name | (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9,10-bis[[(Z)-2-methylbut-2-enoyl]oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid |
| SMILES (Canonical) | CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)C)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)CO)OC(=O)C(=CC)C |
| SMILES (Isomeric) | C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)O)C)C)C)O)CO)(C)C)OC(=O)/C(=C\C)/C |
| InChI | InChI=1S/C57H88O22/c1-12-25(3)47(70)78-44-45(79-48(71)26(4)13-2)57(24-60)28(20-52(44,5)6)27-14-15-32-54(9)18-17-34(53(7,8)31(54)16-19-55(32,10)56(27,11)21-33(57)61)74-51-43(77-50-39(66)37(64)35(62)29(22-58)72-50)41(40(67)42(76-51)46(68)69)75-49-38(65)36(63)30(23-59)73-49/h12-14,28-45,49-51,58-67H,15-24H2,1-11H3,(H,68,69)/b25-12-,26-13-/t28-,29+,30-,31-,32+,33+,34-,35-,36-,37-,38+,39+,40-,41-,42-,43+,44-,45-,49-,50-,51+,54-,55+,56+,57-/m0/s1 |
| InChI Key | MBJDXKFGFVRQIV-GZBYFAPJSA-N |
| Popularity | 1 reference in papers |
| Molecular Formula | C57H88O22 |
| Molecular Weight | 1125.30 g/mol |
| Exact Mass | 1124.57672443 g/mol |
| Topological Polar Surface Area (TPSA) | 348.00 Ų |
| XlogP | 4.30 |
| Atomic LogP (AlogP) | 1.29 |
| H-Bond Acceptor | 21 |
| H-Bond Donor | 11 |
| Rotatable Bonds | 14 |
| RefChem:109975 |
| (2S,3S,4S,5R,6R)-6-(((3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9,10-bis(((Z)-2-methylbut-2-enoyl)oxy)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl)oxy)-4-((2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)oxy-3-hydroxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxane-2-carboxylic acid |
| (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9,10-bis[[(Z)-2-methylbut-2-enoyl]oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid |
| CHEMBL1094675 |
| Xanifolia Y10 |
| BDBM50317507 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.8427 | 84.27% |
| Caco-2 | - | 0.8661 | 86.61% |
| Blood Brain Barrier | - | 0.5000 | 50.00% |
| Human oral bioavailability | - | 0.7857 | 78.57% |
| Subcellular localzation | Mitochondria | 0.8733 | 87.33% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.7597 | 75.97% |
| OATP1B3 inhibitior | + | 0.8381 | 83.81% |
| MATE1 inhibitior | - | 0.9800 | 98.00% |
| OCT2 inhibitior | - | 0.5250 | 52.50% |
| BSEP inhibitior | + | 0.9563 | 95.63% |
| P-glycoprotein inhibitior | + | 0.7471 | 74.71% |
| P-glycoprotein substrate | - | 0.6040 | 60.40% |
| CYP3A4 substrate | + | 0.7341 | 73.41% |
| CYP2C9 substrate | - | 0.8018 | 80.18% |
| CYP2D6 substrate | - | 0.8966 | 89.66% |
| CYP3A4 inhibition | - | 0.8187 | 81.87% |
| CYP2C9 inhibition | - | 0.8372 | 83.72% |
| CYP2C19 inhibition | - | 0.9259 | 92.59% |
| CYP2D6 inhibition | - | 0.9408 | 94.08% |
| CYP1A2 inhibition | - | 0.9133 | 91.33% |
| CYP2C8 inhibition | + | 0.7523 | 75.23% |
| CYP inhibitory promiscuity | - | 0.9476 | 94.76% |
| UGT catelyzed | + | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.9700 | 97.00% |
| Carcinogenicity (trinary) | Non-required | 0.4689 | 46.89% |
| Eye corrosion | - | 0.9891 | 98.91% |
| Eye irritation | - | 0.8984 | 89.84% |
| Skin irritation | + | 0.5000 | 50.00% |
| Skin corrosion | - | 0.9368 | 93.68% |
| Ames mutagenesis | - | 0.7678 | 76.78% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.7124 | 71.24% |
| Micronuclear | - | 0.7900 | 79.00% |
| Hepatotoxicity | - | 0.8296 | 82.96% |
| skin sensitisation | - | 0.9098 | 90.98% |
| Respiratory toxicity | - | 0.5778 | 57.78% |
| Reproductive toxicity | + | 0.9556 | 95.56% |
| Mitochondrial toxicity | + | 0.5500 | 55.00% |
| Nephrotoxicity | + | 0.4561 | 45.61% |
| Acute Oral Toxicity (c) | III | 0.6742 | 67.42% |
| Estrogen receptor binding | + | 0.7250 | 72.50% |
| Androgen receptor binding | + | 0.7548 | 75.48% |
| Thyroid receptor binding | + | 0.6174 | 61.74% |
| Glucocorticoid receptor binding | + | 0.7927 | 79.27% |
| Aromatase binding | + | 0.6289 | 62.89% |
| PPAR gamma | + | 0.8154 | 81.54% |
| Honey bee toxicity | - | 0.6471 | 64.71% |
| Biodegradation | - | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | - | 0.5700 | 57.00% |
| Fish aquatic toxicity | + | 0.9692 | 96.92% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1781 | P11387 | DNA topoisomerase I |
23800 nM 27100 nM |
IC50 IC50 |
PMID: 20371180
PMID: 20371180 |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 98.26% | 91.11% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 95.80% | 96.09% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 94.38% | 94.45% |
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 93.38% | 90.17% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 88.97% | 95.56% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 88.21% | 99.17% |
| CHEMBL2111367 | P27986 | PI3-kinase p110-alpha/p85-alpha | 87.65% | 94.33% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 87.21% | 95.89% |
| CHEMBL2581 | P07339 | Cathepsin D | 85.75% | 98.95% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 85.28% | 86.33% |
| CHEMBL3807 | P17706 | T-cell protein-tyrosine phosphatase | 85.06% | 93.00% |
| CHEMBL5255 | O00206 | Toll-like receptor 4 | 84.71% | 92.50% |
| CHEMBL4187 | Q99250 | Sodium channel protein type II alpha subunit | 84.50% | 95.50% |
| CHEMBL3880 | P07900 | Heat shock protein HSP 90-alpha | 84.40% | 96.21% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 83.45% | 95.50% |
| CHEMBL3359 | P21462 | Formyl peptide receptor 1 | 82.44% | 93.56% |
| CHEMBL2007 | P16234 | Platelet-derived growth factor receptor alpha | 82.04% | 91.07% |
| CHEMBL1937 | Q92769 | Histone deacetylase 2 | 81.84% | 94.75% |
| CHEMBL4227 | P25090 | Lipoxin A4 receptor | 81.78% | 100.00% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 81.29% | 100.00% |
| CHEMBL2563 | Q9UQL6 | Histone deacetylase 5 | 81.23% | 89.67% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 80.83% | 97.09% |
| CHEMBL1907602 | P06493 | Cyclin-dependent kinase 1/cyclin B1 | 80.76% | 91.24% |
| CHEMBL5028 | O14672 | ADAM10 | 80.14% | 97.50% |
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.
To see more specific details click the taxa you are interested in.
| Aesculus chinensis |
| Aesculus pavia |
| Xanthoceras sorbifolium |
| PubChem | 11788101 |
| NPASS | NPC25998 |
| ChEMBL | CHEMBL1094675 |
| LOTUS | LTS0232503 |
| wikiData | Q105160795 |