(1S)-1alpha-(beta-D-Glucopyranosyloxy)-1,4aalpha,5,6,7,7aalpha-hexahydrocyclopenta[c]pyran-4,7alpha-dicarboxylic acid dimethyl ester
| Internal ID | 57b850e7-d44a-4d0e-80f0-91153d92fc8d |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides |
| IUPAC Name | dimethyl (1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4,7-dicarboxylate |
| SMILES (Canonical) | COC(=O)C1CCC2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O |
| SMILES (Isomeric) | COC(=O)[C@H]1CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OC)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O |
| InChI | InChI=1S/C18H26O11/c1-25-15(23)8-4-3-7-9(16(24)26-2)6-27-17(11(7)8)29-18-14(22)13(21)12(20)10(5-19)28-18/h6-8,10-14,17-22H,3-5H2,1-2H3/t7-,8+,10-,11+,12-,13+,14-,17+,18+/m1/s1 |
| InChI Key | KVSFLKZCIIGPEC-SVEKQWPTSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C18H26O11 |
| Molecular Weight | 418.40 g/mol |
| Exact Mass | 418.14751164 g/mol |
| Topological Polar Surface Area (TPSA) | 161.00 Ų |
| XlogP | -1.20 |
| Atomic LogP (AlogP) | -1.97 |
| H-Bond Acceptor | 11 |
| H-Bond Donor | 4 |
| Rotatable Bonds | 5 |
| There are no found synonyms. |
![2D Structure of (1S)-1alpha-(beta-D-Glucopyranosyloxy)-1,4aalpha,5,6,7,7aalpha-hexahydrocyclopenta[c]pyran-4,7alpha-dicarboxylic acid dimethyl ester](https://plantaedb.com/storage/docs/compounds/2023/07/51b8acd0-26b3-11ee-a666-8f0d53cb8b60.jpg "2D Structure of (1S)-1alpha-(beta-D-Glucopyranosyloxy)-1,4aalpha,5,6,7,7aalpha-hexahydrocyclopenta[c]pyran-4,7alpha-dicarboxylic acid dimethyl ester")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | - | 0.5751 | 57.51% |
| Caco-2 | - | 0.8476 | 84.76% |
| Blood Brain Barrier | - | 0.5500 | 55.00% |
| Human oral bioavailability | - | 0.8429 | 84.29% |
| Subcellular localzation | Mitochondria | 0.7764 | 77.64% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.7243 | 72.43% |
| OATP1B3 inhibitior | + | 0.9497 | 94.97% |
| MATE1 inhibitior | - | 1.0000 | 100.00% |
| OCT2 inhibitior | - | 0.7750 | 77.50% |
| BSEP inhibitior | - | 0.8289 | 82.89% |
| P-glycoprotein inhibitior | - | 0.7732 | 77.32% |
| P-glycoprotein substrate | - | 0.8156 | 81.56% |
| CYP3A4 substrate | + | 0.6172 | 61.72% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8719 | 87.19% |
| CYP3A4 inhibition | - | 0.9040 | 90.40% |
| CYP2C9 inhibition | - | 0.8561 | 85.61% |
| CYP2C19 inhibition | - | 0.8895 | 88.95% |
| CYP2D6 inhibition | - | 0.9065 | 90.65% |
| CYP1A2 inhibition | - | 0.8588 | 85.88% |
| CYP2C8 inhibition | - | 0.6223 | 62.23% |
| CYP inhibitory promiscuity | - | 0.8237 | 82.37% |
| UGT catelyzed | - | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 1.0000 | 100.00% |
| Carcinogenicity (trinary) | Non-required | 0.6715 | 67.15% |
| Eye corrosion | - | 0.9870 | 98.70% |
| Eye irritation | - | 0.9541 | 95.41% |
| Skin irritation | - | 0.7434 | 74.34% |
| Skin corrosion | - | 0.9414 | 94.14% |
| Ames mutagenesis | - | 0.5570 | 55.70% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4812 | 48.12% |
| Micronuclear | - | 0.7400 | 74.00% |
| Hepatotoxicity | - | 0.7625 | 76.25% |
| skin sensitisation | - | 0.8886 | 88.86% |
| Respiratory toxicity | + | 0.5222 | 52.22% |
| Reproductive toxicity | + | 0.8222 | 82.22% |
| Mitochondrial toxicity | + | 0.5750 | 57.50% |
| Nephrotoxicity | + | 0.6694 | 66.94% |
| Acute Oral Toxicity (c) | III | 0.5302 | 53.02% |
| Estrogen receptor binding | + | 0.7388 | 73.88% |
| Androgen receptor binding | + | 0.5769 | 57.69% |
| Thyroid receptor binding | - | 0.5668 | 56.68% |
| Glucocorticoid receptor binding | - | 0.5925 | 59.25% |
| Aromatase binding | - | 0.6165 | 61.65% |
| PPAR gamma | - | 0.6112 | 61.12% |
| Honey bee toxicity | - | 0.8523 | 85.23% |
| Biodegradation | - | 0.7250 | 72.50% |
| Crustacea aquatic toxicity | - | 0.7600 | 76.00% |
| Fish aquatic toxicity | - | 0.5267 | 52.67% |
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 | 97.18% | 96.09% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 96.05% | 91.11% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 93.28% | 97.09% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 85.18% | 99.17% |
| CHEMBL5255 | O00206 | Toll-like receptor 4 | 84.40% | 92.50% |
| CHEMBL218 | P21554 | Cannabinoid CB1 receptor | 84.25% | 96.61% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 84.17% | 96.00% |
| CHEMBL3476 | O15111 | Inhibitor of nuclear factor kappa B kinase alpha subunit | 82.10% | 95.83% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 81.69% | 94.73% |
| CHEMBL4016 | P42262 | Glutamate receptor ionotropic, AMPA 2 | 81.64% | 86.92% |
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