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

Database connections

Structure pdb 6DRZ
Ligand site mutations 5-HT1A 5-HT1B 5-HT2A 5-HT2B 5-HT2C 5-HT6

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-HT1F 5HT1F Human 5-Hydroxytryptamine A pKi 8.2 8.2 8.2 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 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
5-HT6 5HT6R Rat 5-Hydroxytryptamine A pKi 6.4 6.5 6.6 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-HT7 5HT7R Mouse 5-Hydroxytryptamine A pKi 8.1 8.1 8.1 Drug Central
5-HT1B 5HT1B Rat 5-Hydroxytryptamine A pKi 5.74 6.19 6.51 PDSP Ki database
5-HT2C K7GSR7 Pig 5-Hydroxytryptamine A pKi 8.49 8.65 8.9 PDSP Ki database
5-HT1B 5HT1B Human 5-Hydroxytryptamine A pKi 6.79 8.03 8.6 PDSP Ki database
5-HT1A F6Q2H9 Bovine 5-Hydroxytryptamine A pKi 7.4 7.4 7.4 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-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-HT6 5HT6R Human 5-Hydroxytryptamine A pKi 6.43 7.0 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 Human 5-Hydroxytryptamine A pKi 7.08 7.19 7.52 PDSP Ki database
5-HT7 5HT7R Mouse 5-Hydroxytryptamine A pKi 7.9 7.9 7.9 PDSP Ki database
5-HT1A 5HT1A Rat 5-Hydroxytryptamine A pKi 5.33 6.94 7.67 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
M1 ACM1 Human Acetylcholine (muscarinic) A pKi 5.26 5.26 5.26 PDSP Ki database
M2 ACM2 Human Acetylcholine (muscarinic) A pKi 5.21 5.21 5.21 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
α2A ADA2A Human Adrenoceptors A pKi 6.77 6.77 6.77 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
D2 DRD2 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
D3 DRD3 Rat Dopamine 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
H1 HRH1 Guinea pig Histamine A pKi 5.52 5.52 5.52 PDSP Ki database
5-HT5A 5HT5A Human 5-Hydroxytryptamine A pKi 5.0 5.0 5.0 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-HT2A 5HT2A Human 5-Hydroxytryptamine A pKi 8.02 8.02 8.02 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
α2A ADA2A Human Adrenoceptors A pKi 8.21 8.21 8.21 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-HT2A 5HT2A Rat 5-Hydroxytryptamine A pKi 8.06 8.06 8.06 Drug Central
5-HT5A 5HT5A Rat 5-Hydroxytryptamine A pKi 8.17 8.17 8.17 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
M3 ACM3 Human Acetylcholine (muscarinic) A pKi 8.27 8.27 8.27 Drug Central
M3 ACM3 Human Acetylcholine (muscarinic) A pKi 5.33 5.33 5.33 PDSP Ki database
5-HT1A 5HT1A Human 5-Hydroxytryptamine A pKi 8.12 8.12 8.12 Drug Central
5-HT1E 5HT1E Human 5-Hydroxytryptamine A pKi 6.5 6.65 6.8 Guide to Pharmacology
5-HT2A 5HT2A Human 5-Hydroxytryptamine A pKi 8.4 8.4 8.4 Guide to Pharmacology
α2B ADA2B Human Adrenoceptors A pKi 6.97 6.97 6.97 PDSP Ki database
α2B ADA2B Human Adrenoceptors A pKi 8.25 8.25 8.25 Drug Central
D4 DRD4 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 8.4 8.38 9.5 Guide to Pharmacology
mGlu2 GRM2 Rat Metabotropic glutamate C pKi 5.0 5.0 5.0 PDSP Ki database
5-HT1B 5HT1B Rat 5-Hydroxytryptamine A pKi 8.16 8.16 8.16 Drug Central
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