Citrulline

Details

• Internal ID: 0d3a66f7-8920-406f-9739-04346df06e23
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Alpha amino acids > L-alpha-amino acids
• IUPAC Name: (2S)-2-amino-5-(carbamoylamino)pentanoic acid
• SMILES (Canonical): C(CC(C(=O)O)N)CNC(=O)N
• SMILES (Isomeric): 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
• InChI Key: RHGKLRLOHDJJDR-BYPYZUCNSA-N
• Popularity: 13,165 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₁₃N₃O₃
• Molecular Weight: 175.19 g/mol
• Exact Mass: 175.09569129 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: -4.30

Synonyms

• citrulline
• 372-75-8
• H-cit-oh
• delta-Ureidonorvaline
• Sitrulline
• (S)-2-Amino-5-ureidopentanoic acid
• N5-Carbamoyl-L-ornithine
• L-Cytrulline
• Citrulline, L-
• N(delta)-Carbamylornithine
• N5-(Aminocarbonyl)ornithine
• N5-carbamoylornithine
• Ornithine, N5-(aminocarbonyl)-
• L(+)-citrulline
• alpha-Amino-delta-ureidovaleric acid
• L-2-Amino-5-ureidovaleric acid
• (2S)-2-amino-5-(carbamoylamino)pentanoic acid
• L-Ornithine, N5-(aminocarbonyl)-
• 2-Amino-5-ureidovaleric acid
• N5-(Aminocarbonyl)-L-ornithine
• UNII-29VT07BGDA
• EINECS 206-759-6
• 29VT07BGDA
• MFCD00064397
• NSC 27425
• Ornithine, N5-carbamoyl-, L-
• CHEBI:16349
• Ngamma-carbamylornithine
• N(5)-(aminocarbonyl)-L-ornithine
• NSC-27425
• N(5)-carbamoyl-L-ornithine
• L-citrullin
• DTXSID80883373
• d-ureidonorvaline
• gamma-ureidonorvaline
• N(SUP 5)-(AMINOCARBONYL)-L-ORNITHINE
• CITRULLINE (MART.)
• CITRULLINE [MART.]
• 2-Amino-5-uredovaleric acid
• 94740-46-2
• CIR
• L-CITRULLINE (USP-RS)
• L-CITRULLINE [USP-RS]
• L-(+)-Citrulline
• (2S)-2-Amino-5-(carbamoylamino)pentanoic Acid (Citrulline)
• Ornithine, N5-carbamoyl-, L- (8CI)
• N(5)-carbamoylornithine
• N5-carbamylornithine
• N~5~-carbamoyl-L-ornithine
• C6H13N3O3
• Cytrulline
• Ureidonorvaline
• Ureidovalerate
• H-Orn(carbamoyl)-OH;L-Citrulline
• L-Citruline
• gammaureidonorvaline
• N-carbamylornithine
• L-Citrulline, 4
• Amino-ureidovalerate
• ND-carbamylornithine
• L-Citrulline,(S)
• L(+)-Citrulline;
• N()-carbamylornithine
• L-Citrulline (DCF)
• L-Citrulline, 98%
• Ndelta-Carbamylornithine
• starbld0002494
• Amino-ureidovaleric acid
• Ndelta-carbamy-ornithine
• CITRULLINE [MI]
• A-amino-d-ureidovalerate
• 2-Amino-5-uredovalerate
• CITRULLINE [INCI]
• 2-Amino-5-ureidovalerate
• L-N5-carbamoyl-Ornithine
• CITRULLINE [VANDF]
• bmse000032
• bmse000800
• bmse000858
• CITRULLINE [WHO-DD]
• A-amino-d-ureidovaleric acid
• L-2-Amino-5-ureidovalerate
• SCHEMBL20588
• GTPL722
• (2S)-2-amino-5-(aminocarbonylamino)pentanoic acid
• N5-(aminocarbonyl)-Ornithine
• L-2-Amino-5-ureido-valerate
• CHEMBL444814
• Alpha-amino-delta-ureidovalerate
• Alpha-amino-gamma-ureidovalerate
• SCHEMBL13254095
• BDBM92903
• (S)-2-Amino-5-ureidopentanoate
• L(+)-2-Amino-5-ureidovalerate
• L-2-Amino-5-ureido-valeric acid
• L-Citrulline, >=98% (TLC)
• DTXCID301022909
• HY-N0391
• L(+)-2-Amino-5-ureidovaleric acid
• s3798
• AKOS005259571
• AKOS006240677
• AM82461
• CCG-266398
• CS-W019940
• DB00155
• SMP1_000146
• NCGC00142602-01
• AC-23976
• AS-12594
• (2S)-2-amino-5-(carbamoylamino)pentanoate
• (S)-2-amino-5-(aminocarbonyl)aminopentanoate
• C00327
• D07706
• D71216
• EN300-251063
• M03230
• (S)-2-amino-5-(aminocarbonyl)aminopentanoic acid
• A823585
• Q408641
• W-202536
• EA65B21D-61C4-4748-9E9F-0CF6EDF9A21D
• Z1198149761
• L-Citrulline, United States Pharmacopeia (USP) Reference Standard

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.09%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.34%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.88%	99.17%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	90.15%	92.29%
CHEMBL233	P35372	Mu opioid receptor	89.55%	97.93%
CHEMBL2581	P07339	Cathepsin D	88.77%	98.95%
CHEMBL2514	O95665	Neurotensin receptor 2	88.68%	100.00%
CHEMBL1795117	Q8TEK3	Histone-lysine N-methyltransferase, H3 lysine-79 specific	88.63%	93.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.58%	91.11%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	88.39%	97.29%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.74%	97.21%
CHEMBL221	P23219	Cyclooxygenase-1	85.56%	90.17%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	84.94%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.38%	96.95%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.21%	85.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.76%	95.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.72%	100.00%
CHEMBL1255126	O15151	Protein Mdm4	83.54%	90.20%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.21%	94.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.08%	96.47%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.93%	94.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.65%	93.56%
CHEMBL2185	Q96GD4	Serine/threonine-protein kinase Aurora-B	80.64%	96.80%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	80.44%	94.01%

Plants that contains it

• Allium sativum
• Arabidopsis thaliana
• Cycas revoluta
• Juncus roemerianus
• Opuntia ficus-indica
• Prunus domestica

Cross-Links

• PubChem: 9750
• LOTUS: LTS0065454
• wikiData: Q408641