Lysergide

Ligand id: 17

Name: Lysergide

Abbreviated name: LSD

Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 39.34
Molecular weight 323.2
XLogP 2.42
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

References
1. Almaula N, Ebersole BJ, Zhang D, Weinstein H, Sealfon SC. (1996)
Mapping the binding site pocket of the serotonin 5-Hydroxytryptamine2A receptor. Ser3.36(159) provides a second interaction site for the protonated amine of serotonin but not of lysergic acid diethylamide or bufotenin.
J. Biol. Chem., 271 (25): 14672-5. [PMID:8663249]
2. 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]
3. 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]
4. Egan C, Grinde E, Dupre A, Roth BL, Hake M, Teitler M, Herrick-Davis K. (2000)
Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors.
Synapse, 35: 144-150. [PMID:10611640]
5. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM. (2002)
Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD).
J. Med. Chem., 45 (19): 4344-9. [PMID:12213075]
6. Wacker D, Wang C, Katritch V, Han GW, Huang XP, Vardy E, McCorvy JD, Jiang Y, Chu M, Siu FY et al.. (2013)
Structural features for functional selectivity at serotonin receptors.
Science, 340 (6132): 615-9. [PMID:23519215]
7. Wacker D, Wang S, McCorvy JD, Betz RM, Venkatakrishnan AJ, Levit A, Lansu K, Schools ZL, Che T, Nichols DE et al.. (2017)
Crystal Structure of an LSD-Bound Human Serotonin Receptor.
Cell, 168 (3): 377-389.e12. [PMID:28129538]