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L-citrulline zwitterion

AlkaPlorer ID: AK002885

Synonym: '', 'N5-(Aminocarbonyl)ornithine', 'Cit\nSitrulline\nCitrulline\nL-Citrulline\nL-Cytrulline\nCITRULLINE,(L)\n.delta.-Ureidonorvaline\nN5-Carbamoyl-L-ornithine\nN.delta.-Carbamylornithine\nN(.delta.)-Carbamylornithine', 'alpha-amino-delta-ureidovaleric acid', '(S)-2-Amino-5-ureidopentanoic acid', '372-75-8', 'citrulina', 'CITRULLINE', 'L-citrulline', 'L-2-Amino-5-ureidovaleric acid', 'Citrullin', 'delta-ureidonorvaline', '2-Amino-5-ureidovaleric acid', '(2S)-2-azaniumyl-5-(carbamoylamino)pentanoate', 'L-Citrulline', 'N(5)-(aminocarbonyl)ornithine', 'N(delta)-carbamylornithine', 'Citrulline', 'Cit', '2-Amino-5-uredovaleric acid', '627-77-0', 'N(5)-(aminocarbonyl)-DL-ornithine', 'N(5)-carbamoyl-DL-ornithine', 'dl-citrulline', 'N5-carbamoylornithine', 'DL-2-amino-5-ureidovaleric acid', 'N(5)-(aminocarbonyl)-L-ornithine', 'citrulline'

IUPAC Name: (2S)-2-amino-5-(carbamoylamino)pentanoic acid

Structure

SMILES: N=C(O)NCCC[C@H](N)C(=O)O

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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

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InChIKey: RHGKLRLOHDJJDR-BYPYZUCNSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Carpesium triste Carpesium Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Daucus carota Daucus Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Paralithodes brevipes Paralithodes Lithodidae Decapoda Malacostraca Arthropoda Metazoa Eukaryota
Coriolopsis gallica Coriolopsis Polyporaceae Polyporales Agaricomycetes Basidiomycota Fungi Eukaryota
Hordeum vulgare Hordeum Poaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Corydalis tashiroi Corydalis Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Nekemias chaffanjonii Nekemias Vitaceae Vitales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lobularia maritima Lobularia Brassicaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cucumis melo Cucumis Cucurbitaceae Cucurbitales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Nezara viridula Nezara Pentatomidae Hemiptera Insecta Arthropoda Metazoa Eukaryota
Guizotia scabra Guizotia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Avena sativa Avena Poaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Amelanchier alnifolia Amelanchier Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Capsicum annuum Capsicum Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Polysiphonia nigra Polysiphonia Rhodomelaceae Ceramiales Florideophyceae Rhodophyta None Eukaryota
Brassica rapa Brassica Brassicaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Arum palaestinum Arum Araceae Alismatales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Prunus tomentosa Prunus Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ammoides pusilla Ammoides Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Rubus idaeus Rubus Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Raoulia australis Raoulia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Beta vulgaris Beta Chenopodiaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Royena zombensis Royena Ebenaceae Ericales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Homo sapiens Homo Hominidae Primates Mammalia Chordata Metazoa Eukaryota
Hyla arborea Hyla Hylidae Anura Amphibia Chordata Metazoa Eukaryota
Cucurbita maxima Cucurbita Cucurbitaceae Cucurbitales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Arabidopsis thaliana Arabidopsis Brassicaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Euphorbia cuneata Euphorbia Euphorbiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Prunus speciosa Prunus Rosaceae Rosales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Mikania cordifolia Mikania Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Frasera albicaulis Frasera Gentianaceae Gentianales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Piper nigrum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Phaseolus vulgaris Phaseolus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Glycyrrhiza glabra Glycyrrhiza Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Saccharomyces cerevisiae Saccharomyces Saccharomycetaceae Saccharomycetales Saccharomycetes Ascomycota Fungi Eukaryota
Pastinaca sativa Pastinaca Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Terminalia brachystemma Terminalia Combretaceae Myrtales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Lolium rigidum Lolium Poaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hakea trifurcata Hakea Proteaceae Proteales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Prosopis juliflora Prosopis Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cucurbita pepo Cucurbita Cucurbitaceae Cucurbitales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ustilaginoidea virens Ustilaginoidea Clavicipitaceae Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota
Spinacia oleracea Spinacia Chenopodiaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Solanum tuberosum Solanum Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Mus musculus Mus Muridae Rodentia Mammalia Chordata Metazoa Eukaryota
Anacyclus monanthos Anacyclus Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Solanum melongena Solanum Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cucumis sativus Cucumis Cucurbitaceae Cucurbitales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Anethum graveolens Anethum Apiaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Allium cepa Allium Amaryllidaceae Asparagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Astragalus angustifolius Astragalus Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Brassica oleracea Brassica Brassicaceae Brassicales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Escherichia coli Escherichia Enterobacteriaceae Enterobacterales Gammaproteobacteria Pseudomonadota None Bacteria
Otholobium glandulosum Otholobium Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Chondria armata Chondria Rhodomelaceae Ceramiales Florideophyceae Rhodophyta None Eukaryota
Lactuca sativa Lactuca Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Secale cereale Secale Poaceae Poales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Litchi chinensis Litchi Sapindaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 175.188

TPSA？: 119.43

MolLogP？: -0.7391300000000005

Number of H-Donors: 5

Number of H-Acceptors: 3

RingCount: 0

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Acetylcholinesterase AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-1a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Estrogen receptor alpha AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Solute carrier organic anion transporter family member 1B1 Inhibition 135.09 % 10.1124/mol.112.084152
Homo sapiens Solute carrier organic anion transporter family member 1B3 Inhibition 119.67 % 10.1124/mol.112.084152
Homo sapiens Thrombin AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vascular endothelial growth factor receptor 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Saccharomyces cerevisiae General amino-acid permease GAP1 Activity nan None 10.1038/nchembio.132
Saccharomyces cerevisiae General amino-acid permease GAP1 Inhibition nan % 10.1038/nchembio.132
Saccharomyces cerevisiae General amino-acid permease GAP1 Km 37000.0 nM 10.1038/nchembio.132
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 17.14 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 30.93 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Hit score 0.1542 None 10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -3.08 % 10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.07 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.26 % 10.6019/CHEMBL4495565
None No relevant target Kd 68000.0 nM 10.1021/jm030650o
None Unchecked Activity nan None 10.1038/nchembio.132
None Unchecked Inhibition 0.0 % 10.1016/j.bmc.2007.12.040
None Unchecked Inhibition nan % 10.1038/nchembio.132

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT002074 CC(=O)C(=O)O.NC(=O)NCCC[C@H](N)C(=O)O>>C[C@@H](N[C@@H](CCCNC(N)=O)C(=O)O)C(=O)O enzymemap_22873
AKRT002657 CC(=O)N[C@@H](CCCNC(N)=O)C(=O)O>>NC(=O)NCCC[C@H](N)C(=O)O RXN-7933
AKRT010355 CN(C)C(=N)NCCC[C@H](N)C(=O)O>>CNC.NC(=O)NCCC[C@H](N)C(=O)O None
AKRT010357 CN(C)C(=N)NCCC[C@H](N)C(=O)O>>NC(=O)NCCC[C@H](N)C(=O)O DIMETHYLARGININASE-RXN
AKRT010657 CNC(=N)NCCC[C@H](N)C(=O)O>>CN.NC(=O)NCCC[C@H](N)C(=O)O None
AKRT010659 CNC(=N)NCCC[C@H](N)C(=O)O>>NC(=O)NCCC[C@H](N)C(=O)O 25173
AKRT014869 Cc1cc(=O)oc2cc(NC(=O)C(N)CCCNC(N)=O)ccc12>>NC(=O)NCCC[C@H](N)C(=O)O enzymemap_72781
AKRT014900 Cc1cc(=O)oc2cc(NC(=O)[C@@H](N)CCCNC(N)=O)ccc12>>NC(=O)NCCC[C@H](N)C(=O)O enzymemap_71990
AKRT015826 N/C(=N/O)NCCC[C@H](N)C(=O)O>>NC(=O)NCCC[C@H](N)C(=O)O R00111
AKRT016098 N=C(N)NCCC[C@H](N)C(=O)O>>NC(=O)NCCC[C@H](N)C(=O)O ARGININE-DEIMINASE-RXN
AKRT016292 N=C(NN)NCCC[C@H](N)C(=O)O>>NC(=O)NCCC[C@H](N)C(=O)O enzymemap_79019
AKRT016295 N=C(NO)NCCC[C@H](N)C(=O)O>>NC(=O)NCCC[C@H](N)C(=O)O RXN-13565
AKRT017066 NC(=O)NCCCC(=O)C(=O)O>>NC(=O)NCCC[C@H](N)C(=O)O enzymemap_41919
AKRT017074 NC(=O)NCCC[C@H](N)C(=O)Nc1ccc2ccccc2c1>>NC(=O)NCCC[C@H](N)C(=O)O enzymemap_72784
AKRT017075 NC(=O)NCCC[C@H](N)C(=O)O.N[C@@H](CC(=O)O)C(=O)O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>N=C(NCCC[C@H](N)C(=O)O)N[C@@H](CC(=O)O)C(=O)O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O None
AKRT017076 NC(=O)NCCC[C@H](N)C(=O)O.N[C@@H](CC(=O)O)C(=O)O>>N=C(NCCC[C@H](N)C(=O)O)NC(CC(=O)O)C(=O)O ARGSUCCINSYN-RXN
AKRT017077 NC(=O)NCCC[C@H](N)C(=O)O.N[C@@H](CC(=O)O)C(=O)O>>N=C(NCCC[C@H](N)C(=O)O)N[C@@H](CC(=O)O)C(=O)O R01954
AKRT017078 NC(=O)NCCC[C@H](N)C(=O)O>>N/C(=N/O)NCCCC(N)C(=O)O MNXR102007
AKRT017079 NC(=O)NCCC[C@H](N)C(=O)O>>N=C(N)NCCC[C@H](N)C(=O)O R00552
AKRT017080 NC(=O)NCCC[C@H](N)C(=O)O>>NC(=O)NCCCC(=O)C(=O)O enzymemap_22127
AKRT017081 NC(=O)NCCC[C@H](N)C(=O)O>>NC(=O)NCCC[C@@H](N)C(=O)O enzymemap_86840
AKRT017082 NC(=O)NCCC[C@H](N)C(=O)O>>NC(=O)OP(=O)(O)O ORNCARBAMTRANSFER-RXN
AKRT017083 NC(=O)NCCC[C@H](N)C(=O)O>>NC(=O)OP(=O)(O)O.NCCC[C@H](N)C(=O)O None
AKRT017084 NC(=O)NCCC[C@H](N)C(=O)O>>NC(=O)O[As](=O)(O)O enzymemap_28129
AKRT017085 NC(=O)NCCC[C@H](N)C(=O)O>>NCCCC(N)C(=O)O MNXR180479
AKRT017086 NC(=O)NCCC[C@H](N)C(=O)O>>NCCC[C@H](N)C(=O)O ORNCARBAMTRANSFER-RXN
AKRT017087 NC(=O)NCCC[C@H](N)C(=O)O>>NCCC[C@H](N)C(=O)O.O=C=O None
AKRT017088 NC(=O)NCCC[C@H](N)C(=O)O>>N[C@@H](CCCNC(=O)O)C(=O)O enzymemap_65153
AKRT017089 NC(=O)NCCC[C@H](N)C(=O)O>>O=C(O)O MNXR180479
AKRT017090 NC(=O)NCCC[C@H](N)C(=O)O>>O=C=O enzymemap_76877
AKRT017146 NC(=O)OP(=O)(O)O.NCCCC(N)C(=O)O>>NC(=O)NCCC[C@H](N)C(=O)O MNXR179124
AKRT017157 NC(=O)OP(=O)(O)O.NCCC[C@H](N)C(=O)O>>NC(=O)NCCC[C@H](N)C(=O)O R01398
AKRT017184 NC(=O)O[As](=O)(O)O.NCCC[C@H](N)C(=O)O>>NC(=O)NCCC[C@H](N)C(=O)O enzymemap_28129
AKRT018254 NCCC[C@H](N)C(=O)O.O=C(O)O>>NC(=O)NCCC[C@H](N)C(=O)O MNXR133864
AKRT018256 NCCC[C@H](N)C(=O)O.O=C=O>>NC(=O)NCCC[C@H](N)C(=O)O MNXR179312
AKRT018660 N[C@@H](CC(=O)O)C(=O)O.NC(=O)NCCC[C@H](N)C(=O)O>>N=C(NCCC[C@H](N)C(=O)O)N[C@@H](CC(=O)O)C(=O)O enzymemap_91270
AKRT019001 N[C@@H](CCC(=O)Nc1ccc([N+](=O)[O-])cc1)C(=O)O.NC(=O)NCCC[C@H](N)C(=O)O>>NC(=O)NCCC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)O enzymemap_32936