methysergide
| SMILES | CC[C@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)cn3C)CO |
| InChIKey | KPJZHOPZRAFDTN-ZRGWGRIASA-N |
Chemical properties
| Hydrogen bond acceptors | 4 |
| Hydrogen bond donors | 2 |
| Rotatable bonds | 4 |
| Molecular weight (Da) | 353.2 |
Drug properties
| Molecular type | Small molecule |
| Physiological/Surrogate | Surrogate |
| Approved drug | Yes |
Bioactivities
| Receptor | Activity | Source | |||||||
|---|---|---|---|---|---|---|---|---|---|
| GTP | Uniprot | Species | Family | Class | Type | Min | Avg | Max | Database |
| 5-HT1B | 5HT1B | Human | 5-Hydroxytryptamine | A | pKi | 6.6 | 7.1 | 7.6 | Guide to Pharmacology |
| 5-HT1D | 5HT1D | Human | 5-Hydroxytryptamine | A | pKi | 8.4 | 8.65 | 8.9 | Guide to Pharmacology |
| 5-HT1E | 5HT1E | Human | 5-Hydroxytryptamine | A | pKi | 6.5 | 6.65 | 6.8 | Guide to Pharmacology |
| 5-HT1F | 5HT1F | Human | 5-Hydroxytryptamine | A | pKi | 8.2 | 8.2 | 8.2 | Guide to Pharmacology |
| 5-HT2A | 5HT2A | Human | 5-Hydroxytryptamine | A | pKi | 8.4 | 8.4 | 8.4 | Guide to Pharmacology |
| 5-HT2B | 5HT2B | Human | 5-Hydroxytryptamine | A | pKi | 8.0 | 8.7 | 9.4 | Guide to Pharmacology |
| 5-HT2C | 5HT2C | Human | 5-Hydroxytryptamine | A | pKi | 8.6 | 8.85 | 9.1 | Guide to Pharmacology |
| 5-HT5A | 5HT5A | Human | 5-Hydroxytryptamine | A | pKi | 7.0 | 7.0 | 7.0 | Guide to Pharmacology |
| 5-HT6 | 5HT6R | Rat | 5-Hydroxytryptamine | A | pKi | 6.4 | 6.5 | 6.6 | Guide to Pharmacology |
| 5-HT2A | 5HT2A | Rat | 5-Hydroxytryptamine | A | pKi | 8.4 | 8.38 | 9.5 | Guide to Pharmacology |
| 5-HT5A | 5HT5A | Rat | 5-Hydroxytryptamine | A | pKi | 6.7 | 6.7 | 6.7 | Guide to Pharmacology |
| 5-HT2C | 5HT2C | Rat | 5-Hydroxytryptamine | A | pKi | 9.0 | 9.0 | 9.0 | Guide to Pharmacology |
| 5-HT7 | 5HT7R | Mouse | 5-Hydroxytryptamine | A | pKi | 7.9 | 7.9 | 7.9 | Guide to Pharmacology |
| 5-HT7 | 5HT7R | Rat | 5-Hydroxytryptamine | A | pKi | 7.9 | 7.9 | 7.9 | Guide to Pharmacology |
| 5-HT2B | 5HT2B | Rat | 5-Hydroxytryptamine | A | pKi | 8.2 | 8.2 | 8.2 | Guide to Pharmacology |
| 5-HT5A | 5HT5A | Mouse | 5-Hydroxytryptamine | A | pKi | 6.3 | 6.75 | 7.2 | Guide to Pharmacology |
| 5-HT1B | 5HT1B | Rat | 5-Hydroxytryptamine | A | pKi | 6.97 | 6.97 | 6.97 | ChEMBL |
| α2B | ADA2B | Human | Adrenoceptors | A | pKi | 5.66 | 5.66 | 5.66 | ChEMBL |
| 5-HT1A | 5HT1A | Rat | 5-Hydroxytryptamine | A | pKi | 7.51 | 7.51 | 7.51 | ChEMBL |
| α2A | ADA2A | Human | Adrenoceptors | A | pKi | 6.21 | 6.21 | 6.21 | ChEMBL |
| D1 | DRD1 | Human | Dopamine | A | pKi | 6.33 | 6.33 | 6.33 | ChEMBL |
| 5-HT6 | 5HT6R | Human | 5-Hydroxytryptamine | A | pKi | 7.12 | 7.12 | 7.12 | ChEMBL |
| 5-HT2B | 5HT2B | Human | 5-Hydroxytryptamine | A | pKi | 8.12 | 8.6 | 9.45 | ChEMBL |
| 5-HT2C | 5HT2C | Human | 5-Hydroxytryptamine | A | pKi | 8.6 | 8.89 | 9.1 | ChEMBL |
| D3 | DRD3 | Human | Dopamine | A | pKi | 7.23 | 7.23 | 7.23 | ChEMBL |
| 5-HT2A | 5HT2A | Human | 5-Hydroxytryptamine | A | pKi | 8.0 | 8.21 | 8.42 | ChEMBL |
| 5-HT1A | 5HT1A | Human | 5-Hydroxytryptamine | A | pKi | 7.77 | 7.77 | 7.77 | ChEMBL |
| D2 | DRD2 | Human | Dopamine | A | pKi | 6.57 | 6.57 | 6.57 | ChEMBL |
| 5-HT1D | 5HT1D | Human | 5-Hydroxytryptamine | A | pKi | 7.03 | 7.49 | 8.44 | PDSP Ki database |
| 5-HT1D | 5HT1D | Rat | 5-Hydroxytryptamine | A | pKi | 7.0 | 7.2 | 7.39 | PDSP Ki database |
| 5-HT1D | F1MMU1 | Bovine | 5-Hydroxytryptamine | A | pKi | 6.92 | 8.15 | 8.42 | PDSP Ki database |
| 5-HT1B | 5HT1B | Rat | 5-Hydroxytryptamine | A | pKi | 5.74 | 6.19 | 6.51 | PDSP Ki database |
| 5-HT1A | 5HT1A | Rat | 5-Hydroxytryptamine | A | pKi | 5.33 | 6.94 | 7.67 | PDSP Ki database |
| 5-HT2A | 5HT2A | Human | 5-Hydroxytryptamine | A | pKi | 6.98 | 8.16 | 8.8 | PDSP Ki database |
| 5-HT2A | 5HT2A | Rat | 5-Hydroxytryptamine | A | pKi | 7.82 | 8.61 | 9.38 | PDSP Ki database |
| 5-HT2A | 5HT2A | Pig | 5-Hydroxytryptamine | A | pKi | 7.58 | 7.58 | 7.58 | PDSP Ki database |
| 5-HT6 | 5HT6R | Rat | 5-Hydroxytryptamine | A | pKi | 6.4 | 6.47 | 6.59 | PDSP Ki database |
| 5-HT5A | 5HT5A | Mouse | 5-Hydroxytryptamine | A | pKi | 6.3 | 7.0 | 7.2 | PDSP Ki database |
| 5-HT7 | 5HT7R | Rat | 5-Hydroxytryptamine | A | pKi | 6.4 | 7.67 | 7.9 | PDSP Ki database |
| 5-HT6 | 5HT6R | Human | 5-Hydroxytryptamine | A | pKi | 6.43 | 7.0 | 7.52 | PDSP Ki database |
| 5-HT1B | 5HT1B | Human | 5-Hydroxytryptamine | A | pKi | 6.79 | 8.03 | 8.6 | PDSP Ki database |
| 5-HT2C | 5HT2C | Rat | 5-Hydroxytryptamine | A | pKi | 8.7 | 8.92 | 9.1 | PDSP Ki database |
| 5-HT2B | 5HT2B | Human | 5-Hydroxytryptamine | A | pKi | 6.82 | 8.65 | 10.0 | PDSP Ki database |
| 5-HT2C | 5HT2C | Human | 5-Hydroxytryptamine | A | pKi | 8.35 | 8.72 | 9.02 | PDSP Ki database |
| 5-HT5A | 5HT5A | Rat | 5-Hydroxytryptamine | A | pKi | 6.0 | 6.36 | 6.71 | PDSP Ki database |
| 5-HT2B | 5HT2B | Rat | 5-Hydroxytryptamine | A | pKi | 7.06 | 7.97 | 8.2 | PDSP Ki database |
| 5-HT7 | 5HT7R | Guinea pig | 5-Hydroxytryptamine | A | pKi | 7.03 | 7.36 | 7.65 | PDSP Ki database |
| 5-HT7 | 5HT7R | Human | 5-Hydroxytryptamine | A | pKi | 7.08 | 7.19 | 7.52 | PDSP Ki database |
| 5-HT1E | 5HT1E | Human | 5-Hydroxytryptamine | A | pKi | 6.49 | 6.7 | 7.23 | PDSP Ki database |
| 5-HT6 | 5HT6R | Mouse | 5-Hydroxytryptamine | A | pKi | 7.9 | 7.9 | 7.9 | PDSP Ki database |
| 5-HT1F | 5HT1F | Human | 5-Hydroxytryptamine | A | pKi | 7.47 | 7.47 | 7.47 | PDSP Ki database |
| H1 | HRH1 | Rat | Histamine | A | pKi | 4.48 | 4.74 | 5.0 | PDSP Ki database |
| D1 | DRD1 | Rat | Dopamine | A | pKi | 6.66 | 6.66 | 6.66 | PDSP Ki database |
| D2 | DRD2 | Rat | Dopamine | A | pKi | 6.94 | 6.94 | 6.94 | PDSP Ki database |
| D1 | DRD1 | Bovine | Dopamine | A | pKi | 5.8 | 6.17 | 6.54 | PDSP Ki database |
| 5-HT1A | 5HT1A | Human | 5-Hydroxytryptamine | A | pKi | 7.6 | 7.73 | 7.85 | PDSP Ki database |
| 5-HT1D | 5HT1D | Dog | 5-Hydroxytryptamine | A | pKi | 8.11 | 8.11 | 8.11 | PDSP Ki database |
| 5-HT1F | 5HT1F | Mouse | 5-Hydroxytryptamine | A | pKi | 8.2 | 8.2 | 8.2 | PDSP Ki database |
| 5-HT1F | 5HT1F | Rat | 5-Hydroxytryptamine | A | pKi | 7.87 | 7.87 | 7.87 | PDSP Ki database |
| 5-HT2B | 5HT2B | Mouse | 5-Hydroxytryptamine | A | pKi | 7.9 | 7.9 | 7.9 | PDSP Ki database |
| 5-HT7 | 5HT7R | Mouse | 5-Hydroxytryptamine | A | pKi | 7.9 | 7.9 | 7.9 | PDSP Ki database |
| D2 | DRD2 | Bovine | Dopamine | A | pKi | 6.8 | 6.8 | 6.8 | PDSP Ki database |
| 5-HT1B | 5HT1B | Guinea pig | 5-Hydroxytryptamine | A | pKi | 6.73 | 6.73 | 6.73 | PDSP Ki database |
| 5-HT5A | 5HT5A | Human | 5-Hydroxytryptamine | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| M1 | ACM1 | Human | Acetylcholine (muscarinic) | A | pKi | 5.26 | 5.26 | 5.26 | PDSP Ki database |
| M3 | ACM3 | Human | Acetylcholine (muscarinic) | A | pKi | 5.33 | 5.33 | 5.33 | PDSP Ki database |
| M4 | ACM4 | Human | Acetylcholine (muscarinic) | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| M5 | ACM5 | Human | Acetylcholine (muscarinic) | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| α1B | ADA1B | Human | Adrenoceptors | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| α1D | ADA1D | Human | Adrenoceptors | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| α2B | ADA2B | Human | Adrenoceptors | A | pKi | 6.97 | 6.97 | 6.97 | PDSP Ki database |
| α2C | ADA2C | Human | Adrenoceptors | A | pKi | 7.05 | 7.05 | 7.05 | PDSP Ki database |
| β1 | ADRB1 | Human | Adrenoceptors | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| β2 | ADRB2 | Human | Adrenoceptors | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| D1 | DRD1 | Human | Dopamine | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| D4 | DRD4 | Human | Dopamine | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| D5 | DRD5 | Human | Dopamine | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| H1 | HRH1 | Human | Histamine | A | pKi | 5.0 | 5.19 | 5.52 | PDSP Ki database |
| H2 | HRH2 | Human | Histamine | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| EP3 | PE2R3 | Human | Prostanoid | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| CB1 | CNR1 | Rat | Cannabinoid | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| mGlu5 | GRM5 | Rat | Metabotropic glutamate | C | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| mGlu1 | GRM1 | Rat | Metabotropic glutamate | C | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| mGlu8 | GRM8 | Rat | Metabotropic glutamate | C | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| mGlu4 | GRM4 | Rat | Metabotropic glutamate | C | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| 5-HT2C | K7GSR7 | Pig | 5-Hydroxytryptamine | A | pKi | 8.49 | 8.65 | 8.9 | PDSP Ki database |
| H1 | HRH1 | Guinea pig | Histamine | A | pKi | 5.52 | 5.52 | 5.52 | PDSP Ki database |
| 5-HT1B | 5HT1B | Human | 5-Hydroxytryptamine | A | pKi | 8.12 | 8.12 | 8.12 | Drug Central |
| 5-HT1D | 5HT1D | Human | 5-Hydroxytryptamine | A | pKi | 8.05 | 8.05 | 8.05 | Drug Central |
| 5-HT1E | 5HT1E | Human | 5-Hydroxytryptamine | A | pKi | 8.17 | 8.17 | 8.17 | Drug Central |
| 5-HT1F | 5HT1F | Human | 5-Hydroxytryptamine | A | pKi | 8.09 | 8.09 | 8.09 | Drug Central |
| 5-HT2B | 5HT2B | Human | 5-Hydroxytryptamine | A | pKi | 8.03 | 8.03 | 8.03 | Drug Central |
| 5-HT2C | 5HT2C | Human | 5-Hydroxytryptamine | A | pKi | 8.08 | 8.08 | 8.08 | Drug Central |
| 5-HT5A | 5HT5A | Human | 5-Hydroxytryptamine | A | pKi | 8.15 | 8.15 | 8.15 | Drug Central |
| 5-HT6 | 5HT6R | Human | 5-Hydroxytryptamine | A | pKi | 8.17 | 8.17 | 8.17 | Drug Central |
| 5-HT7 | 5HT7R | Human | 5-Hydroxytryptamine | A | pKi | 8.11 | 8.11 | 8.11 | Drug Central |
| M1 | ACM1 | Human | Acetylcholine (muscarinic) | A | pKi | 8.28 | 8.28 | 8.28 | Drug Central |
| M2 | ACM2 | Human | Acetylcholine (muscarinic) | A | pKi | 8.28 | 8.28 | 8.28 | Drug Central |
| M3 | ACM3 | Human | Acetylcholine (muscarinic) | A | pKi | 8.27 | 8.27 | 8.27 | Drug Central |
| α2B | ADA2B | Human | Adrenoceptors | A | pKi | 8.25 | 8.25 | 8.25 | Drug Central |
| α2C | ADA2C | Human | Adrenoceptors | A | pKi | 8.15 | 8.15 | 8.15 | Drug Central |
| D1 | DRD1 | Human | Dopamine | A | pKi | 8.2 | 8.2 | 8.2 | Drug Central |
| D2 | DRD2 | Human | Dopamine | A | pKi | 8.18 | 8.18 | 8.18 | Drug Central |
| D3 | DRD3 | Human | Dopamine | A | pKi | 8.14 | 8.14 | 8.14 | Drug Central |
| H1 | HRH1 | Human | Histamine | A | pKi | 8.26 | 8.26 | 8.26 | Drug Central |
| 5-HT6 | 5HT6R | Rat | 5-Hydroxytryptamine | A | pKi | 8.18 | 8.18 | 8.18 | Drug Central |
| 5-HT5A | 5HT5A | Rat | 5-Hydroxytryptamine | A | pKi | 8.17 | 8.17 | 8.17 | Drug Central |
| 5-HT7 | 5HT7R | Mouse | 5-Hydroxytryptamine | A | pKi | 8.1 | 8.1 | 8.1 | Drug Central |
| 5-HT1B | 5HT1B | Rat | 5-Hydroxytryptamine | A | pKi | 8.16 | 8.16 | 8.16 | Drug Central |
| 5-HT7 | 5HT7R | Rat | 5-Hydroxytryptamine | A | pKi | 8.1 | 8.1 | 8.1 | Drug Central |
| 5-HT5A | 5HT5A | Mouse | 5-Hydroxytryptamine | A | pKi | 8.14 | 8.14 | 8.14 | Drug Central |
| 5-HT1A | 5HT1A | Human | 5-Hydroxytryptamine | A | pKi | 8.12 | 8.12 | 8.12 | Drug Central |
| 5-HT2A | 5HT2A | Human | 5-Hydroxytryptamine | A | pKi | 8.02 | 8.02 | 8.02 | Drug Central |
| 5-HT6 | 5HT6R | Human | 5-Hydroxytryptamine | A | pKi | 6.5 | 6.65 | 6.8 | Guide to Pharmacology |
| 5-HT7 | 5HT7R | Human | 5-Hydroxytryptamine | A | pKi | 7.1 | 7.45 | 7.8 | Guide to Pharmacology |
| M2 | ACM2 | Human | Acetylcholine (muscarinic) | A | pKi | 5.21 | 5.21 | 5.21 | PDSP Ki database |
| α2A | ADA2A | Human | Adrenoceptors | A | pKi | 8.21 | 8.21 | 8.21 | Drug Central |
| α2A | ADA2A | Human | Adrenoceptors | A | pKi | 6.77 | 6.77 | 6.77 | PDSP Ki database |
| D2 | DRD2 | Human | Dopamine | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| EP4 | PE2R4 | Human | Prostanoid | A | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| 5-HT2A | 5HT2A | Rat | 5-Hydroxytryptamine | A | pKi | 8.06 | 8.06 | 8.06 | Drug Central |
| mGlu2 | GRM2 | Rat | Metabotropic glutamate | C | pKi | 5.0 | 5.0 | 5.0 | PDSP Ki database |
| 5-HT1A | F6Q2H9 | Bovine | 5-Hydroxytryptamine | A | pKi | 7.4 | 7.4 | 7.4 | PDSP Ki database |
| 5-HT1A | A0A4X1UTF5 | Pig | 5-Hydroxytryptamine | A | pKi | 7.63 | 7.63 | 7.63 | PDSP Ki database |
| Receptor | Activity | Source | |||||||
|---|---|---|---|---|---|---|---|---|---|
| GTP | Uniprot | Species | Family | Class | Type | Min | Avg | Max | Database |
| 5-HT1F | 5HT1F | Rat | 5-Hydroxytryptamine | A | pIC50 | 7.8 | 7.8 | 7.8 | Guide to Pharmacology |
| 5-HT1B | 5HT1B | Rat | 5-Hydroxytryptamine | A | pIC50 | 6.75 | 6.75 | 6.75 | ChEMBL |
| α2B | ADA2B | Human | Adrenoceptors | A | pIC50 | 5.32 | 5.32 | 5.32 | ChEMBL |
| 5-HT1A | 5HT1A | Rat | 5-Hydroxytryptamine | A | pIC50 | 7.27 | 7.27 | 7.27 | ChEMBL |
| α2A | ADA2A | Human | Adrenoceptors | A | pIC50 | 5.79 | 5.79 | 5.79 | ChEMBL |
| D1 | DRD1 | Human | Dopamine | A | pIC50 | 6.03 | 6.03 | 6.03 | ChEMBL |
| 5-HT6 | 5HT6R | Human | 5-Hydroxytryptamine | A | pIC50 | 6.79 | 6.79 | 6.79 | ChEMBL |
| 5-HT2B | 5HT2B | Human | 5-Hydroxytryptamine | A | pIC50 | 9.25 | 9.25 | 9.25 | ChEMBL |
| 5-HT2C | 5HT2C | Human | 5-Hydroxytryptamine | A | pIC50 | 8.68 | 8.68 | 8.68 | ChEMBL |
| D3 | DRD3 | Human | Dopamine | A | pIC50 | 6.76 | 6.76 | 6.76 | ChEMBL |
| 5-HT2A | 5HT2A | Human | 5-Hydroxytryptamine | A | pIC50 | 7.89 | 7.89 | 7.89 | ChEMBL |
| D2 | DRD2 | Human | Dopamine | A | pIC50 | 6.09 | 6.09 | 6.09 | ChEMBL |
| 5-HT1A | 5HT1A | Rat | 5-Hydroxytryptamine | A | pIC50 | 8.14 | 8.14 | 8.14 | Drug Central |
| 5-HT1F | 5HT1F | Rat | 5-Hydroxytryptamine | A | pIC50 | 8.11 | 8.11 | 8.11 | Drug Central |