[(1R,4aS,5R,7aR)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
| Internal ID | 0efb0b45-3d5c-48b5-a000-eda07659a624 |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides |
| IUPAC Name | [(1R,4aS,5R,7aR)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate |
| SMILES (Canonical) | C1=COC(C2C1C(C=C2COC(=O)C3=CC=C(C=C3)O)O)OC4C(C(C(C(O4)CO)O)O)O |
| SMILES (Isomeric) | C1=CO[C@@H]([C@@H]2[C@H]1[C@H](C=C2COC(=O)C3=CC=C(C=C3)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O |
| InChI | InChI=1S/C22H26O11/c23-8-15-17(26)18(27)19(28)22(32-15)33-21-16-11(7-14(25)13(16)5-6-30-21)9-31-20(29)10-1-3-12(24)4-2-10/h1-7,13-19,21-28H,8-9H2/t13-,14+,15-,16+,17-,18+,19-,21-,22+/m1/s1 |
| InChI Key | GLACGTLACKLUJX-FRAFBTIOSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C22H26O11 |
| Molecular Weight | 466.40 g/mol |
| Exact Mass | 466.14751164 g/mol |
| Topological Polar Surface Area (TPSA) | 175.00 Ų |
| XlogP | -1.10 |
| Atomic LogP (AlogP) | -1.23 |
| H-Bond Acceptor | 11 |
| H-Bond Donor | 6 |
| Rotatable Bonds | 6 |
| AKOS025311586 |
| AC-34704 |
| ((1R,4aS,5R,7aR)-5-hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl)methyl 4-hydroxybenzoate |
![2D Structure of [(1R,4aS,5R,7aR)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate](https://plantaedb.com/storage/docs/compounds/2023/07/c3ea3f00-2546-11ee-9786-c16976208aca.jpg "2D Structure of [(1R,4aS,5R,7aR)-5-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.6298 | 62.98% |
| Caco-2 | - | 0.9141 | 91.41% |
| Blood Brain Barrier | - | 0.5500 | 55.00% |
| Human oral bioavailability | - | 0.7857 | 78.57% |
| Subcellular localzation | Mitochondria | 0.6247 | 62.47% |
| OATP2B1 inhibitior | - | 0.8487 | 84.87% |
| OATP1B1 inhibitior | + | 0.8166 | 81.66% |
| OATP1B3 inhibitior | + | 0.9624 | 96.24% |
| MATE1 inhibitior | - | 0.9000 | 90.00% |
| OCT2 inhibitior | - | 0.9250 | 92.50% |
| BSEP inhibitior | - | 0.5486 | 54.86% |
| P-glycoprotein inhibitior | - | 0.7030 | 70.30% |
| P-glycoprotein substrate | - | 0.7685 | 76.85% |
| CYP3A4 substrate | + | 0.6128 | 61.28% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8515 | 85.15% |
| CYP3A4 inhibition | - | 0.9134 | 91.34% |
| CYP2C9 inhibition | - | 0.8779 | 87.79% |
| CYP2C19 inhibition | - | 0.7286 | 72.86% |
| CYP2D6 inhibition | - | 0.8416 | 84.16% |
| CYP1A2 inhibition | - | 0.8379 | 83.79% |
| CYP2C8 inhibition | + | 0.6918 | 69.18% |
| CYP inhibitory promiscuity | - | 0.5536 | 55.36% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 1.0000 | 100.00% |
| Carcinogenicity (trinary) | Non-required | 0.6364 | 63.64% |
| Eye corrosion | - | 0.9897 | 98.97% |
| Eye irritation | - | 0.9340 | 93.40% |
| Skin irritation | - | 0.7884 | 78.84% |
| Skin corrosion | - | 0.9592 | 95.92% |
| Ames mutagenesis | - | 0.6637 | 66.37% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5709 | 57.09% |
| Micronuclear | - | 0.5567 | 55.67% |
| Hepatotoxicity | - | 0.8250 | 82.50% |
| skin sensitisation | - | 0.8116 | 81.16% |
| Respiratory toxicity | - | 0.5667 | 56.67% |
| Reproductive toxicity | + | 0.7778 | 77.78% |
| Mitochondrial toxicity | + | 0.6000 | 60.00% |
| Nephrotoxicity | + | 0.6123 | 61.23% |
| Acute Oral Toxicity (c) | III | 0.4333 | 43.33% |
| Estrogen receptor binding | + | 0.6891 | 68.91% |
| Androgen receptor binding | + | 0.6285 | 62.85% |
| Thyroid receptor binding | + | 0.5158 | 51.58% |
| Glucocorticoid receptor binding | - | 0.6375 | 63.75% |
| Aromatase binding | + | 0.5696 | 56.96% |
| PPAR gamma | + | 0.6194 | 61.94% |
| Honey bee toxicity | - | 0.7778 | 77.78% |
| Biodegradation | - | 0.5750 | 57.50% |
| Crustacea aquatic toxicity | - | 0.7550 | 75.50% |
| Fish aquatic toxicity | + | 0.8179 | 81.79% |
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 | 94.86% | 91.11% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 91.69% | 99.17% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 88.77% | 96.09% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 88.22% | 86.33% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 86.40% | 97.09% |
| CHEMBL3891 | P07384 | Calpain 1 | 85.48% | 93.04% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 84.83% | 94.73% |
| CHEMBL5852 | Q96P65 | Pyroglutamylated RFamide peptide receptor | 83.54% | 85.00% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 82.70% | 89.00% |
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