| Ingredient Name | Brevelin A |
| Pubchem CID | 12302076 |
| Iupac name | [(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,5-b]furan-9-yl] (Z)-2-methylbut-2-enoate |
| Molecular Formula | C20H26O5 |
| Molecular Weight | 346.4 |
| Isomeric smiles | C/C=C(/C)\C(=O)O[C@H]1[C@@H]2[C@@H](C(=O)O[C@@H]2C[C@H]([C@H]3[C@]1(C(=O)C=C3)C)C)C |
| InChI | InChI=1S/C20H26O5/c1-6-10(2)18(22)25-17-16-12(4)19(23)24-14(16)9-11(3)13-7-8-15(21)20(13,17)5/h6-8,11-14,16-17H,9H2,1-5H3/b10-6-/t11-,12+,13+,14-,16-,17+,20+/m1/s1 |
| InChIKey | KUPPZVXLWANEJJ-UXPPPGSFSA-N |
| External Database Links | HERB2.0: HBIN018833 HIT2: C0535 SymMap: SMIT12589 TCM-ID: TCMC2653 ChEMBL: CHEMBL2262842 |
| nHA(Number of hydrogen bond acceptors) | 5 |
| nHD(Number of hydrogen bond donors) | 0 |
| nRot(Number of rotatable bonds) | 3 |
| nRing(Number of rings) | 3 |
| MaxRing(Number of atoms in the biggest ring) | 13 |
| nHet(Number of heteroatoms) | 5 |
| nRig(Number of rigid bonds) | 19 |
| Flexibility | 0.158 |
| Stereo Centers(Number of stereocenters) | 7 |
| TPSA(Topological polar surface area) | 69.67 |
| logS(The logarithm of aqueous solubility value) | -3.448 |
| logP(The logarithm of the n-octanol/water distribution coefficient) | 2.76 |
| logD7.4(The logarithm of the n-octanol/water distribution coefficients at pH=7.4) | 3.025 |
| Quantitative Estimate of Drug-likeness | 0.568 |
| Synthetic accessibility score | 4.871 |
| Natural Product-likeness score | 3.535 |
| Lipinski Rule | Accepted |
| GSK Rule | Accepted |
| Golden Triangle | Accepted |
| Caco-2 Permeability | -4.665 |
| MDCK Permeability | 4.39E-05 |
| Pgp-substrate | 0 |
| HIA(human intestinal absorption) | 0.004 |
| F20%(20% Oral Bioavailability) | 0.144 |
| F30%(30% Oral Bioavailability) | 0.985 |
| PPB(Plasma protein binding) | 92.81% |
| VD(Volume Distribution) | 0.59 |
| BBB Penetration(Blood brain barrier penetration) | 0.241 |
| B3 Penetration(Blood brain barrier penetration) | Permeable |
| Fu(The fraction unbound in plasms) | 11.55% |
| CYP1A2 inhibitor | 0.545 |
| CYP1A2 substrate | 0.104 |
| CYP2C19 inhibitor | 0.099 |
| CYP2C19 substrate | 0.812 |
| CYP2C9 inhibitor | 0.27 |
| CYP2C9 substrate | 0.024 |
| CYP2D6 inhibitor | 0.008 |
| CYP2D6 substrate | 0.056 |
| CYP3A4 inhibitor | 0.67 |
| CYP3A4 substrate | 0.433 |
| CL(The clearance of a drug) | 11.084 |
| T1/2 | 0.669 |
| NonBiodegradable Rule | 1 |
| Pfizer Rule | Accepted |
| SR-MMP | 0.355 |
| FDAMDD(FDA Maximum (Recommended) Daily Dose) | 0.455 |
| IGC50 | 4.314 |
| LC50FM | 5.938 |
| LC50DM | 6.562 |
| NR-AR(Androgen receptor) | 0.182 |
| NR-AR-LBD(Androgen receptor) | 0.555 |
| NR-Aromatase | 0.847 |
| NR-ER(Estrogen receptor) | 0.114 |
| NR-ER-LBD(Estrogen receptor) | 0.031 |
| Skin Sensitization Rule | 2 |
| Skin Sensitization | 0.87 |
| Acute Toxicity Rule | 5 |
| Rat Oral Acute Toxicity | 0.485 |
| hERG Blockers | 0.117 |
| H-HT(The human hepatotoxicity) | 0.939 |
| DILI(Drug-induced liver injury) | 0.608 |
| Eye Corrosion | 0.062 |
| Eye Irritation | 0.151 |
| Respiratory Toxicity | 0.901 |
| AMES Toxicity | 0.064 |
| Carcinogencity | 0.152 |
| SR-ARE(Antioxidant Response Element) | 0.634 |
| SR-ATAD5(ATPase family AAA domain-containing protein 5) | 0.088 |
| SR-p53 | 0.875 |