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L-citrulline   Click here for help

GtoPdb Ligand ID: 722

PDB Ligand
Compound class: Metabolite
Comment: L-citrulline is a non-essential amino acid. Some mammalian proteins naturally contain citrulline residues (myelin basic protein, some histone proteins and filaggrin).
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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

L-citrulline is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 6
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 118.44
Molecular weight 175.1
XLogP -3.91
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NC(=O)NCCCC(C(=O)O)N
Isomeric SMILES NC(=O)NCCC[C@@H](C(=O)O)N
InChI InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
InChI Key RHGKLRLOHDJJDR-BYPYZUCNSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Metabolite
IUPAC Name Click here for help
(2S)-2-amino-5-(carbamoylamino)pentanoic acid
Database Links Click here for help
Specialist databases
GPCRdb Ligand L-citrulline
Other databases
CAS Registry No. 372-75-8 (source: DrugBank)
ChEBI CHEBI:16349
ChEMBL Ligand CHEMBL444814
DrugBank Ligand DB00155
DrugCentral Ligand 3103
GtoPdb PubChem SID 135650512
PubChem CID 9750
RCSB PDB Ligand CIR
Search Google for chemical match using the InChIKey RHGKLRLOHDJJDR-BYPYZUCNSA-N
Search Google for chemicals with the same backbone RHGKLRLOHDJJDR
UniChem Compound Search for chemical match using the InChIKey RHGKLRLOHDJJDR-BYPYZUCNSA-N
UniChem Connectivity Search for chemical match using the InChIKey RHGKLRLOHDJJDR-BYPYZUCNSA-N
Wikipedia Citrulline

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

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MedChemExpress
L-Citrulline (links to external site)
Cat. No. HY-N0391
L-Citrulline (Standard) (links to external site)
Cat. No. HY-N0391R