(3R,4S,5S,6R)-2-[[5-hydroxy-7-(hydroxymethyl)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
| Internal ID | f5322b81-9198-4665-b3cd-caf73376712b |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides |
| IUPAC Name | (3R,4S,5S,6R)-2-[[5-hydroxy-7-(hydroxymethyl)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol |
| SMILES (Canonical) | C1C(C2C(C1O)C=COC2OC3C(C(C(C(O3)CO)O)O)O)CO |
| SMILES (Isomeric) | C1C(C2C(C1O)C=COC2OC3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO |
| InChI | InChI=1S/C15H24O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-2,6-21H,3-5H2/t6?,7?,8?,9-,10?,11-,12+,13-,14?,15?/m1/s1 |
| InChI Key | SXPWHBXTTWFWMH-BIRDSZKRSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C15H24O9 |
| Molecular Weight | 348.34 g/mol |
| Exact Mass | 348.14203234 g/mol |
| Topological Polar Surface Area (TPSA) | 149.00 Ų |
| XlogP | -2.20 |
| Atomic LogP (AlogP) | -2.72 |
| H-Bond Acceptor | 9 |
| H-Bond Donor | 6 |
| Rotatable Bonds | 4 |
| AC-20186 |
![2D Structure of (3R,4S,5S,6R)-2-[[5-hydroxy-7-(hydroxymethyl)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol](https://plantaedb.com/storage/docs/compounds/2023/07/e1cf39a0-266e-11ee-ae51-8fc8da4492f7.jpg "2D Structure of (3R,4S,5S,6R)-2-[[5-hydroxy-7-(hydroxymethyl)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | - | 0.7520 | 75.20% |
| Caco-2 | - | 0.8726 | 87.26% |
| Blood Brain Barrier | + | 0.5750 | 57.50% |
| Human oral bioavailability | - | 0.7857 | 78.57% |
| Subcellular localzation | Mitochondria | 0.4734 | 47.34% |
| OATP2B1 inhibitior | - | 0.8591 | 85.91% |
| OATP1B1 inhibitior | + | 0.8541 | 85.41% |
| OATP1B3 inhibitior | + | 0.9637 | 96.37% |
| MATE1 inhibitior | - | 0.9600 | 96.00% |
| OCT2 inhibitior | - | 0.9250 | 92.50% |
| BSEP inhibitior | - | 0.9831 | 98.31% |
| P-glycoprotein inhibitior | - | 0.8983 | 89.83% |
| P-glycoprotein substrate | - | 0.9265 | 92.65% |
| CYP3A4 substrate | + | 0.5357 | 53.57% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8087 | 80.87% |
| CYP3A4 inhibition | - | 0.9488 | 94.88% |
| CYP2C9 inhibition | - | 0.9665 | 96.65% |
| CYP2C19 inhibition | - | 0.8600 | 86.00% |
| CYP2D6 inhibition | - | 0.8831 | 88.31% |
| CYP1A2 inhibition | - | 0.9178 | 91.78% |
| CYP2C8 inhibition | - | 0.8395 | 83.95% |
| CYP inhibitory promiscuity | - | 0.8927 | 89.27% |
| UGT catelyzed | + | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.9900 | 99.00% |
| Carcinogenicity (trinary) | Non-required | 0.6410 | 64.10% |
| Eye corrosion | - | 0.9920 | 99.20% |
| Eye irritation | - | 0.9715 | 97.15% |
| Skin irritation | - | 0.8382 | 83.82% |
| Skin corrosion | - | 0.9620 | 96.20% |
| Ames mutagenesis | - | 0.5200 | 52.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4038 | 40.38% |
| Micronuclear | - | 0.7441 | 74.41% |
| Hepatotoxicity | - | 0.7802 | 78.02% |
| skin sensitisation | - | 0.9122 | 91.22% |
| Respiratory toxicity | - | 0.5333 | 53.33% |
| Reproductive toxicity | + | 0.6333 | 63.33% |
| Mitochondrial toxicity | - | 0.6500 | 65.00% |
| Nephrotoxicity | - | 0.6409 | 64.09% |
| Acute Oral Toxicity (c) | IV | 0.4304 | 43.04% |
| Estrogen receptor binding | - | 0.8003 | 80.03% |
| Androgen receptor binding | - | 0.6208 | 62.08% |
| Thyroid receptor binding | - | 0.5778 | 57.78% |
| Glucocorticoid receptor binding | - | 0.8174 | 81.74% |
| Aromatase binding | + | 0.5572 | 55.72% |
| PPAR gamma | + | 0.6195 | 61.95% |
| Honey bee toxicity | - | 0.7874 | 78.74% |
| Biodegradation | - | 0.6000 | 60.00% |
| Crustacea aquatic toxicity | - | 0.6552 | 65.52% |
| Fish aquatic toxicity | - | 0.7485 | 74.85% |
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 | 96.23% | 91.11% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 93.78% | 96.09% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 92.59% | 97.09% |
| CHEMBL226 | P30542 | Adenosine A1 receptor | 88.43% | 95.93% |
| CHEMBL4016 | P42262 | Glutamate receptor ionotropic, AMPA 2 | 88.40% | 86.92% |
| CHEMBL218 | P21554 | Cannabinoid CB1 receptor | 83.76% | 96.61% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 82.37% | 97.25% |
| CHEMBL3589 | P55263 | Adenosine kinase | 81.00% | 98.05% |
| CHEMBL3880 | P07900 | Heat shock protein HSP 90-alpha | 80.40% | 96.21% |
| CHEMBL3476 | O15111 | Inhibitor of nuclear factor kappa B kinase alpha subunit | 80.04% | 95.83% |
Below are displayed all the plants proven (via scientific papers) to contain this
compound!
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