Lysergide   Click here for help

GtoPdb Ligand ID: 17

Abbreviated name: LSD
Synonyms: (+)-lysergic acid diethylamide | N,N-diethyllysergamide
PDB Ligand
Compound class: Synthetic organic
Comment: Lysergic acid diethylamide (LSD), also known colloquially as "acid", is a psychedelic drug known for its psychological effects. In 2017 LSD was crystalised in complex with the human serotonin receptor 5-HT2B [7].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCN(C(=O)C1CN(C)C2C(=C1)c1cccc3c1c(C2)c[nH]3)CC
Isomeric SMILES CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC
InChI InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1
InChI Key VAYOSLLFUXYJDT-RDTXWAMCSA-N
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, Bös 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 (3): 577-83. [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 (2): 144-50. [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]