| Ingredient Name | 6-hydroxy-7-methylidene-1-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid |
| Pubchem CID | 22524229 |
| Iupac name | 6-hydroxy-7-methylidene-1-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid |
| Molecular Formula | C16H22O10 |
| Molecular Weight | 374.34 |
| Isomeric smiles | C=C1C(CC2C1C(OC=C2C(=O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](O3)CO)O)O)O)O |
| InChI | InChI=1S/C16H22O10/c1-5-8(18)2-6-7(14(22)23)4-24-15(10(5)6)26-16-13(21)12(20)11(19)9(3-17)25-16/h4,6,8-13,15-21H,1-3H2,(H,22,23)/t6?,8?,9-,10?,11+,12-,13-,15?,16+/m1/s1 |
| InChIKey | JSKCJJNYSGWZDU-BXSUZMQKSA-N |
| External Database Links |
| nHA(Number of hydrogen bond acceptors) | 10 |
| nHD(Number of hydrogen bond donors) | 6 |
| nRot(Number of rotatable bonds) | 4 |
| nRing(Number of rings) | 3 |
| MaxRing(Number of atoms in the biggest ring) | 9 |
| nHet(Number of heteroatoms) | 10 |
| nRig(Number of rigid bonds) | 18 |
| Flexibility | 0.222 |
| Stereo Centers(Number of stereocenters) | 9 |
| TPSA(Topological polar surface area) | 166.14 |
| logS(The logarithm of aqueous solubility value) | -0.29 |
| logP(The logarithm of the n-octanol/water distribution coefficient) | -1.39 |
| logD7.4(The logarithm of the n-octanol/water distribution coefficients at pH=7.4) | -1.145 |
| Quantitative Estimate of Drug-likeness | 0.294 |
| Synthetic accessibility score | 4.827 |
| Natural Product-likeness score | 3.006 |
| Lipinski Rule | Accepted |
| GSK Rule | Accepted |
| Golden Triangle | Accepted |
| Caco-2 Permeability | -6.461 |
| MDCK Permeability | 0.000144919 |
| Pgp-substrate | 0.788 |
| HIA(human intestinal absorption) | 0.912 |
| F20%(20% Oral Bioavailability) | 0.345 |
| F30%(30% Oral Bioavailability) | 0.998 |
| PPB(Plasma protein binding) | 35.83% |
| VD(Volume Distribution) | 0.299 |
| BBB Penetration(Blood brain barrier penetration) | 0.229 |
| B3 Penetration(Blood brain barrier penetration) | Non-Permeable |
| Fu(The fraction unbound in plasms) | 62.46% |
| CYP1A2 inhibitor | 0.012 |
| CYP1A2 substrate | 0.016 |
| CYP2C19 inhibitor | 0.021 |
| CYP2C19 substrate | 0.055 |
| CYP2C9 inhibitor | 0.006 |
| CYP2C9 substrate | 0.067 |
| CYP2D6 inhibitor | 0.014 |
| CYP2D6 substrate | 0.098 |
| CYP3A4 inhibitor | 0.008 |
| CYP3A4 substrate | 0.029 |
| CL(The clearance of a drug) | 1.565 |
| T1/2 | 0.684 |
| NonBiodegradable Rule | 1 |
| Pfizer Rule | Accepted |
| SR-MMP | 0.139 |
| FDAMDD(FDA Maximum (Recommended) Daily Dose) | 0.287 |
| IGC50 | 1.797 |
| LC50FM | 2.573 |
| LC50DM | 3.644 |
| NR-AR(Androgen receptor) | 0.021 |
| NR-AR-LBD(Androgen receptor) | 0.165 |
| NR-Aromatase | 0.002 |
| NR-ER(Estrogen receptor) | 0.088 |
| NR-ER-LBD(Estrogen receptor) | 0.02 |
| Skin Sensitization Rule | 1 |
| Skin Sensitization | 0.048 |
| Acute Toxicity Rule | 4 |
| Rat Oral Acute Toxicity | 0.346 |
| hERG Blockers | 0.025 |
| H-HT(The human hepatotoxicity) | 0.364 |
| DILI(Drug-induced liver injury) | 0.922 |
| Eye Corrosion | 0.003 |
| Eye Irritation | 0.025 |
| Respiratory Toxicity | 0.633 |
| AMES Toxicity | 0.063 |
| Carcinogencity | 0.923 |
| SR-ARE(Antioxidant Response Element) | 0.022 |
| SR-ATAD5(ATPase family AAA domain-containing protein 5) | 0.04 |
| SR-p53 | 0.01 |