| General Information | |
|---|---|
| ZINC ID | taranabant |
| Molecular Weight (Da) | 515 |
| SMILES | N#Cc1cccc(c1)[C@@H]([C@@H](NC(=O)C(Oc1ccc(cn1)C(F)(F)F)(C)C)C)Cc1ccc(cc1)Cl |
| Molecular Formula | C27H25ClF3N3O2 |
| Action | Inverse agonist |
| Physicochemical Details | |
|---|---|
| Molar Refractivity | 131.12 |
| HBA | 5 |
| HBD | 1 |
| Rotatable Bonds | 10 |
| Heavy Atoms | 36 |
| LogP | 7.47 |
| Activity (Ki) in nM | 0.302 |
| Polar Surface Area (PSA) | 75.01 |
| Pharmacokinetic Properties (AdmetSAR) | |
|---|---|
| Human intestinal absorption | + |
| Caco-2 | - |
| Blood brain barrier | + |
| P-glycoprotein inhibitior | + |
| P-glycoprotein substrate | + |
| Cyp3a4 substrate | + |
| Cyp2c9 substrate | + |
| Cyp2d6 substrate | - |
| Cyp3a4 inhibition | + |
| Cyp2c9 inhibition | + |
| Cyp2c19 inhibition | + |
| Cyp2d6 inhibition | - |
| Cyp1a2 inhibition | + |
| Acute oral toxicity | + |
| Carcinogenicity (binary) | - |
| Ames mutagenesis | - |
| Human ether-a-go-go-related gene inhibition | + |
| Biodegradation | - |
| Glucocorticoid receptor binding | + |
| Thyroid receptor binding | + |
| Androgen receptor binding | + |
| Plasma protein binding | 0.99143576 |
| Pharmacokinetic Properties (SwissADME) | |
|---|---|
| Number of aromatic heavy atoms | 18 |
| Fraction csp3 | 0.3 |
| Ilogp | 4.01 |
| Xlogp3 | 6.46 |
| Wlogp | 7.47 |
| Mlogp | 4.11 |
| Silicos-it log p | 6.92 |
| Consensus log p | 5.79 |
| Esol log s | -6.82 |
| Esol solubility (mg/ml) | 0.0000783 |
| Esol solubility (mol/l) | 0.00000015 |
| Esol class | Poorly sol |
| Ali log s | -7.83 |
| Ali solubility (mg/ml) | 0.00000763 |
| Ali solubility (mol/l) | 1.48E-08 |
| Ali class | Poorly sol |
| Silicos-it logsw | -9.9 |
| Silicos-it solubility (mg/ml) | 6.45E-08 |
| Silicos-it solubility (mol/l) | 1.25E-10 |
| Silicos-it class | Poorly soluble |
| Pgp substrate | |
| Log kp (cm/s) | -4.86 |
| Lipinski number of violations | 1 |
| Ghose number of violations | 3 |
| Veber number of violations | 0 |
| Egan number of violations | 1 |
| Muegge number of violations | 1 |
| Bioavailability score | 0.55 |
| Pains number of alerts | 0 |
| Brenk number of alerts | 0 |
| Leadlikeness number of violations | 3 |
| Synthetic accessibility | 4.1 |
| Pharmacokinetic Properties (ADMETLab) | |
|---|---|
| Logs | -6.513 |
| Logd | 4.062 |
| Logp | 6.122 |
| F (20%) | 0.002 |
| F (30%) | 0.001 |
| Mdck | - |
| Ppb | 99.97% |
| Vdss | 1.937 |
| Fu | 0.58% |
| Cyp1a2-inh | 0.407 |
| Cyp1a2-sub | 0.88 |
| Cyp2c19-inh | 0.838 |
| Cyp2c19-sub | 0.13 |
| Cl | 6.363 |
| T12 | 0.01 |
| H-ht | 0.966 |
| Dili | 0.957 |
| Roa | 0.106 |
| Fdamdd | 0.834 |
| Skinsen | 0.021 |
| Ec | 0.003 |
| Ei | 0.008 |
| Respiratory | 0.682 |
| Bcf | 1.772 |
| Igc50 | 4.019 |
| Lc50 | 5.428 |
| Lc50dm | 6.264 |
| Nr-ar | 0.079 |
| Nr-ar-lbd | 0.006 |
| Nr-ahr | 0.009 |
| Nr-aromatase | 0.06 |
| Nr-er | 0.514 |
| Nr-er-lbd | 0.073 |
| Nr-ppar-gamma | 0.074 |
| Sr-are | 0.377 |
| Sr-atad5 | 0.007 |
| Sr-hse | 0.012 |
| Sr-mmp | 0.394 |
| Sr-p53 | 0.2 |
| Vol | 502.226 |
| Dense | 1.026 |
| Flex | 0.5 |
| Nstereo | 2 |
| Nongenotoxic carcinogenicity | 1 |
| Ld50 oral | 0 |
| Genotoxic carcinogenicity mutagenicity | 0 |
| Surechembl | 0 |
| Nonbiodegradable | 4 |
| Skin sensitization | 0 |
| Acute aquatic toxicity | - |
| Toxicophores | 1 |
| Qed | 0.381 |
| Synth | 3.43 |
| Fsp3 | 0.296 |
| Mce-18 | 48 |
| Natural product-likeness | -1.295 |
| Alarm nmr | 1 |
| Bms | 0 |
| Chelating | 0 |
| Pfizer | - |
| Gsk | Rejected |
| Goldentriangle | Rejected |