metergoline   Click here for help

GtoPdb Ligand ID: 133

Synonyms: FI-6337 | liserdol | metergoline phenylmethyl ester
Compound class: Synthetic organic
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 46.5
Molecular weight 403.23
XLogP 4.1
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES O=C(OCc1ccccc1)NCC1CN(C)C2C(C1)c1cccc3c1c(C2)cn3C
Isomeric SMILES O=C(OCc1ccccc1)NC[C@H]1CN(C)[C@H]2[C@H](C1)c1cccc3c1c(C2)cn3C
InChI InChI=1S/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/t18-,21+,23+/m0/s1
InChI Key WZHJKEUHNJHDLS-QTGUNEKASA-N
References
1. Adham N, Bard JA, Zgombick JM, Durkin MM, Kucharewicz S, Weinshank RL, Branchek TA. (1997)
Cloning and characterization of the guinea pig 5-HT1F receptor subtype: a comparison of the pharmacological profile to the human species homolog.
Neuropharmacology, 36 (4-5): 569-76. [PMID:9225282]
2. Adham N, Kao HT, Schecter LE, Bard J, Olsen M, Urquhart D, Durkin M, Hartig PR, Weinshank RL, Branchek TA. (1993)
Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase.
Proc. Natl. Acad. Sci. U.S.A., 90 (2): 408-12. [PMID:8380639]
3. Bai F, Yin T, Johnstone EM, Su C, Varga G, Little SP, Nelson DL. (2004)
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.
Eur. J. Pharmacol., 484 (2-3): 127-39. [PMID:14744596]
4. Bard JA, Zgombick J, Adham N, Vaysse P, Branchek TA, Weinshank RL. (1993)
Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase.
J. Biol. Chem., 268 (31): 23422-6. [PMID:8226867]
5. Boess FG, Monsma FJ, Meyer V, Zwingelstein C, Sleight AJ. (1997)
Interaction of tryptamine and ergoline compounds with threonine 196 in the ligand binding site of the 5-hydroxytryptamine6 receptor.
Mol Pharmacol, 52: 515-523. [PMID:9284367]
6. Boess FG, Monsma Jr FJ, Carolo C, Meyer V, Rudler A, Zwingelstein C, Sleight AJ. (1997)
Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.
Neuropharmacology, 36 (4-5): 713-20. [PMID:9225298]
7. Boess FG, Monsma Jr FJ, Sleight AJ. (1998)
Identification of residues in transmembrane regions III and VI that contribute to the ligand binding site of the serotonin 5-HT6 receptor.
J. Neurochem., 71 (5): 2169-77. [PMID:9798944]
8. Boess FG, Riemer C, Bos M, Bentley J, Bourson A, Sleight AJ. (1998)
The 5-hydroxytryptamine6 receptor-selective radioligand [3H]Ro 63-0563 labels 5-hydroxytryptamine receptor binding sites in rat and porcine striatum.
Mol Pharmacol, 54: 577-583. [PMID:9730917]
9. Doménech T, Beleta J, Palacios JM. (1997)
Characterization of human serotonin 1D and 1B receptors using [3H]-GR-125743, a novel radiolabelled serotonin 5HT1D/1B receptor antagonist.
Naunyn Schmiedebergs Arch. Pharmacol., 356 (3): 328-34. [PMID:9303569]
10. Hamblin MW, Metcalf MA. (1991)
Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor.
Mol. Pharmacol., 40 (2): 143-8. [PMID:1652050]
11. Jasper JR, Kosaka A, To ZP, Chang DJ, Eglen RM. (1997)
Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b).
Br. J. Pharmacol., 122 (1): 126-32. [PMID:9298538]
12. Knight AR, Misra A, Quirk K, Benwell K, Revell D, Kennett G, Bickerdike M. (2004)
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
Naunyn Schmiedebergs Arch. Pharmacol., 370 (2): 114-23. [PMID:15322733]
13. Kohen R, Metcalf MA, Khan N, Druck T, Huebner K, Lachowicz JE, Meltzer HY, Sibley DR, Roth BL, Hamblin MW. (1996)
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.
J. Neurochem., 66 (1): 47-56. [PMID:8522988]
14. Krobert KA, Bach T, Syversveen T, Kvingedal AM, Levy FO. (2001)
The cloned human 5-HT7 receptor splice variants: a comparative characterization of their pharmacology, function and distribution.
Naunyn Schmiedebergs Arch. Pharmacol., 363 (6): 620-32. [PMID:11414657]
15. Leysen JE, Gommeren W, Heylen L, Luyten WH, Van de Weyer I, Vanhoenacker P, Haegeman G, Schotte A, Van Gompel P, Wouters R et al.. (1996)
Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan.
Mol. Pharmacol., 50 (6): 1567-80. [PMID:8967979]
16. Lovenberg TW, Erlander MG, Baron BM, Racke M, Slone AL, Siegel BW, Craft CM, Burns JE, Danielson PE, Sutcliffe JG. (1993)
Molecular cloning and functional expression of 5-HT1E-like rat and human 5-hydroxytryptamine receptor genes.
Proc. Natl. Acad. Sci. U.S.A., 90 (6): 2184-8. [PMID:8384716]
17. McAllister G, Charlesworth A, Snodin C, Beer MS, Noble AJ, Middlemiss DN, Iversen LL, Whiting P. (1992)
Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype.
Proc. Natl. Acad. Sci. U.S.A., 89 (12): 5517-21. [PMID:1608964]
18. Monsma Jr FJ, Shen Y, Ward RP, Hamblin MW, Sibley DR. (1993)
Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs.
Mol. Pharmacol., 43 (3): 320-7. [PMID:7680751]
19. Parker EM, Izzarelli DG, Lewis-Higgins L, Palmer D, Shapiro RA. (1996)
Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors.
J. Neurochem., 67 (5): 2096-103. [PMID:8863519]
20. Plassat JL, Amlaiky N, Hen R. (1993)
Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase.
Mol. Pharmacol., 44 (2): 229-36. [PMID:8394987]
21. Rees S, den Daas I, Foord S, Goodson S, Bull D, Kilpatrick G, Lee M. (1994)
Cloning and characterisation of the human 5-HT5A serotonin receptor.
FEBS Lett., 355 (3): 242-6. [PMID:7988681]
22. Ruat M, Traiffort E, Leurs R, Tardivel-Lacombe J, Diaz J, Arrang JM, Schwartz JC. (1993)
Molecular cloning, characterization, and localization of a high-affinity serotonin receptor (5-HT7) activating cAMP formation.
Proc. Natl. Acad. Sci. U.S.A., 90 (18): 8547-51. [PMID:8397408]
23. Shen Y, Monsma Jr FJ, Metcalf MA, Jose PA, Hamblin MW, Sibley DR. (1993)
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.
J. Biol. Chem., 268 (24): 18200-4. [PMID:8394362]
24. Wainscott DB, Cohen ML, Schenck KW, Audia JE, Nissen JS, Baez M, Kursar JD, Lucaites VL, Nelson DL. (1993)
Pharmacological characteristics of the newly cloned rat 5-hydroxytryptamine2F receptor.
Mol. Pharmacol., 43 (3): 419-26. [PMID:8450835]