CIR

CITRULLINE

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is present as a standalone ligand in 10 entries

as a non-polymer is covalently linked to polymer or other heterogen groups 2 entries

is present in a polymer sequence 53 entries

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Chemical Component Summary
Name	CITRULLINE
Identifiers	(2S)-5-(aminocarbonylamino)-2-azanyl-pentanoic acid
Formula	C₆ H₁₃ N₃ O₃
Molecular Weight	175.186
Type	L-PEPTIDE LINKING
Isomeric SMILES	C(C[C@@H](C(=O)O)N)CNC(=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
InChIKey	RHGKLRLOHDJJDR-BYPYZUCNSA-N

Chemical Details
Formal Charge	0
Atom Count	25
Chiral Atom Count	1
Bond Count	24
Aromatic Bond Count	0

Drug Info: DrugBank

DrugBank ID	DB00155
Name	Citrulline
Groups	investigational nutraceutical
Description	Citrulline is an amino acid. It is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.
Synonyms	δ-ureidonorvaline Citrulline malate Cit N5-Carbamoyl-L-ornithine (S)-2-Amino-5-ureidopentanoic acid Citrulina 2-Amino-5-ureidovaleric acid N(5)-(Aminocarbonyl)-L-ornithine L-Citrulline delta-Ureidonorvaline Citrulline N5-carbamoylornithine N5-(Aminocarbonyl)ornithine L-2-Amino-5-ureidovaleric acid alpha-amino-delta-Ureidovaleric acid N(delta)-Carbamylornithine α-amino-δ-ureidovaleric acid
Brand Names	tensioSAN Lipovite
Indication	Used for nutritional supplementation, also for treating dietary shortage or imbalance.
Categories	Acids, Acyclic Amino Acids Amino Acids, Diamino Amino Acids, Peptides, and Proteins Dicarboxylic Acids Dietary Supplements Hydroxy Acids OAT1/SLC22A6 Substrates OAT3/SLC22A8 Substrates Proteins Supplements
CAS number	372-75-8

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Nitric oxide synthase, endothelial	MGNLKSVAQEPGPPCGLGLGLGLGLCGKQGPATPAPEPSRAPASLLPPAP...	unknown
Argininosuccinate synthase	MSSKGSVVLAYSGGLDTSCILVWLKEQGYDVIAYLANIGQKEDFEEARKK...	unknown
N(G),N(G)-dimethylarginine dimethylaminohydrolase 2	MGTPGEGLGRCSHALIRGVPESLASGEGAGAGLPALDLAKAQREHGVLGG...	unknown
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1	MAGLGHPAAFGRATHAVVRALPESLGQHALRSAKGEEVDVARAERQHQLY...	unknown
Ornithine carbamoyltransferase, mitochondrial	MLFNLRILLNNAAFRNGHNFMVRNFRCGQPLQNKVQLKGRDLLTLKNFTG...	unknown
Nitric oxide synthase, brain	MEDHMFGVQQIQPNVISVRLFKRKVGGLGFLVKERVSKPPVIISDLIRGG...	unknown
Nitric oxide synthase, inducible	MACPWKFLFKTKFHQYAMNGEKDINNNVEKAPCATSSPVTQDDLQYHNLS...	unknown
Protein-arginine deiminase type-4	MAQGTLIRVTPEQPTHAVCVLGTLTQLDICSSAPEDCTSFSINASPGVVV...	unknown
Protein-arginine deiminase type-6	MVSVEGRAMSFQSIIHLSLDSPVHAVCVLGTEICLDLSGCAPQKCQCFTI...	unknown	product of
Protein-arginine deiminase type-1	MAPKRVVQLSLKMPTHAVCVVGVEAHVDIHSDVPKGANSFRVSGSSGVEV...	unknown
Protein-arginine deiminase type-3	MSLQRIVRVSLEHPTSAVCVAGVETLVDIYGSVPEGTEMFEVYGTPGVDI...	unknown
Protein-arginine deiminase type-2	MLRERTVRLQYGSRVEAVYVLGTYLWTDVYSAAPAGAQTFSLKHSEHVWV...	unknown
Solute carrier family 22 member 6	MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682