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Citrulline, (+/-)-

PubChem CID: 833

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Compound Synonyms DL-Citrulline, 627-77-0, 2-Amino-5-ureidopentanoic acid, Citrullin, DL-2-Amino-5-ureidovaleric acid, 2-amino-5-(carbamoylamino)pentanoic acid, citrulina, Citrulline, (+/-)-, 1OYO2NV4NM, CITRULLINE, (DL), DL-Ornithine, N5-(aminocarbonyl)-, Ornithine, N5-carbamoyl-, DL-, EINECS 211-012-2, MFCD00007955, NSC-46711, DL-Ornithine, N(5)-(aminocarbonyl)-, N(5)-carbamoyl-DL-ornithine, N(5)-(aminocarbonyl)ornithine, CHEBI:18211, NSC27425, NSC46711, N(5)-(aminocarbonyl)-DL-ornithine, NSC 46711, N~5~-carbamoylornithine, H-D-Orn(carbamoyl)-OH, NORVALINE, 5-((AMINOCARBONYL)AMINO)-, N(5)-carbamoylornithine, N~5~-carbamoyl-L-ornithine, 2-Amino-5-uredovaleric acid, cit, H-Orn(carbamoyl)-OH, L-Citrulline, MFCD00216469, Citrulline,(l), citrulline (DL-form), Spectrum_000037, .delta.-Ureidonorvaline, CITRULLINE, DL-, SpecPlus_000523, L(+)CITRULLINE, Spectrum2_001371, Spectrum3_001045, Spectrum4_001185, Spectrum5_001792, UNII-1OYO2NV4NM, N.delta.-Carbamylornithine, bmse000209, Epitope ID:141797, SCHEMBL20587, BSPBio_002570, KBioGR_001849, KBioSS_000397, N(.delta.)-Carbamylornithine, DivK1c_006619, SPBio_001322, SGCUT00061, SCHEMBL13282334, KBio1_001563, KBio2_000397, KBio2_002965, KBio2_005533, KBio3_001790, DTXSID40861910, to_000034, BBL027668, CCG-38847, NSC206276, s5124, STK802460, STL455121, AKOS005622468, L-(+)-2-Amino-5-ureidovaleric acid, L-CITRULLINE (1.12117), N~5~-[hydroxy(imino)methyl]ornithine, CS-W017450, HY-W016734, PB48354, SDCCGMLS-0066976.P001, 2aAminoa5a(carbamoylamino)pentanoic acid, 2-azaniumyl-5-(carbamoylamino)pentanoate, NCGC00178596-01, .alpha.-Amino-.delta.-ureidovaleric acid, AS-60168, SY023288, SY032853, SY048344, DB-049088, DB-054282, NS00013538, D89239, EN300-1168657, L000975, SR-05000002410, SR-05000002410-1, BRD-A12237696-001-04-2, Q27102910
Topological Polar Surface Area 118.0
Hydrogen Bond Donor Count 4.0
Heavy Atom Count 12.0
Pathway Kegg Map Id map00330, map00250
Description Occurs in the juice of watermelon (Citrullus vulgaris) A non-essential amino acid and a precursor of arginine. Citrulline supplements have been claimed to promote energy levels, stimulate the immune system and help detoxify ammonia (a cell toxin). L-citrulline is made from L-ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from L-arginine as a by-product of the reaction catalyzed by the enzyme NO synthase. L-citrulline, while being an amino acid, is not involved in protein synthesis and is not one of the amino acids coded for by DNA. Although citrulline cannot be incorporated in proteins during protein synthesis, several proteins are known to contain citrulline as an amino acid. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases (PADs), which convert the amino acid arginine into citrulline. Proteins that contain citrulline residues include myelin basic protein (MBP), fillagrin and several histone proteins., Citrulline is an amino acid 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 (NOS, Citrulline 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 (NOS, EC 1.14.13.39). Arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with release of nitric oxide., EC 1.14.13.39). Citrulline's name is derived from citrullus, the Latin word for watermelon, from which it was first isolated., EC 1.14.13.39). In this reaction arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with the release of nitric oxide., The organic compound citrulline is an ?-amino acid. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated in 1930. It has the idealized formula H2NC(O)NH(CH2)3CH(NH2)CO2H. It is a key intermediate in the urea cycle, the pathway by which mammals excrete ammonia., The rind of watermelon (Citrullus lanatus) is a good natural source of citrulline. L-Citrulline is found in many foods, some of which are mung bean, cucurbita (gourd), nectarine, and acorn.
Isotope Atom Count 0.0
Molecular Complexity 171.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Enzyme Uniprot Id P00966, O95865, P00480, B3VK56
Uniprot Id n.a.
Iupac Name 2-amino-5-(carbamoylamino)pentanoic acid
Prediction Hob 1.0
Class Carboxylic acids and derivatives
Xlogp -4.3
Superclass Organic acids and derivatives
Subclass Amino acids, peptides, and analogues
Molecular Formula C6H13N3O3
Prediction Swissadme 0.0
Inchi Key RHGKLRLOHDJJDR-UHFFFAOYSA-N
Fcsp3 0.6666666666666666
Rotatable Bond Count 5.0
State Solid
Synonyms (2S)-2-amino-5-(carbamoylamino)pentanoate, (2S)-2-amino-5-(carbamoylamino)pentanoic acid, (S)-2-amino-5-(aminocarbonyl)aminopentanoate, (S)-2-amino-5-(aminocarbonyl)aminopentanoic acid, (S)-2-Amino-5-ureidopentanoate, (S)-2-Amino-5-ureidopentanoic acid, 2-Amino-5-uredovalerate, 2-amino-5-Uredovaleric acid, 2-Amino-5-ureidovalerate, 2-Amino-5-ureidovaleric acid, A-amino-d-ureidovalerate, A-amino-d-ureidovaleric acid, a-amino-delta-Ureidovalerate, a-amino-delta-Ureidovaleric acid, a-amino-δ-ureidovalerate, a-amino-δ-ureidovaleric acid, Alpha-amino-delta-ureidovalerate, Alpha-amino-delta-ureidovaleric acid, Alpha-amino-gamma-ureidovalerate, Alpha-amino-gamma-ureidovaleric acid, Amino-ureidovalerate, Amino-ureidovaleric acid, CIR, Cit, CITRULLINE, Citrulline, l-, Citrulline, L-form, Cytrulline, D-ureidonorvaline, Delta-ureidonorvaline, DL-Citrulline, Gammaureidonorvaline, H-cit-oh, L-2-Amino-5-ureido-valerate, L-2-Amino-5-ureido-valeric acid, L-2-Amino-5-ureidovalerate, L-2-Amino-5-ureidovaleric acid, L-citrulline (DCF), L-Cytrulline, L-N5-carbamoyl-Ornithine, L(+)-2-Amino-5-ureidovalerate, L(+)-2-Amino-5-ureidovaleric acid, L(+)-citrulline, N-carbamylornithine, N()-Carbamylornithine, N(5)-(Aminocarbonyl)-DL-ornithine, N(5)-(aminocarbonyl)-L-ornithine, N(5)-carbamoyl-L-ornithine, N(delta)-carbamylornithine, N(δ)-carbamylornithine, N<SUP>5</SUP>-(aminocarbonyl)ornithine, N5-(Aminocarbonyl)-L-ornithine, N5-(aminocarbonyl)-Ornithine, N5-(Aminocarbonyl)ornithine, N5-Carbamoyl-L-ornithine, N5-carbamoylornithine, N5-carbamylornithine, ND-carbamylornithine, Ndelta-carbamy-ornithine, Ndelta-carbamylornithine, Ngamma-carbamylornithine, Ornithine, N5-(aminocarbonyl)-, Ornithine, N5-carbamoyl-, L- (8CI), Sitrulline, Ureidonorvaline, Ureidovalerate, Ureidovaleric acid, α-amino-δ-ureidovalerate, α-amino-δ-ureidovaleric acid, δ-ureidonorvaline, Citrulina, Citrulline, (DL), DL -2-Amino-5-ureidovaleric acid, DL-2-Amino-5-ureidovaleric acid, DL-Ornithine, N(5)-(aminocarbonyl)-, L -2-Amino-5-ureidovaleric acid, L-Ornithine, N(5)-(aminocarbonyl)-, N(5)-(aminocarbonyl)ornithine, N(5)-carbamoyl-DL-ornithine, N(5)-carbamoylornithine, Ornithine, N5-carbamoyl-, DL-, 2-Amino-5-uredovaleric acid, N(5)-(Aminocarbonyl)ornithine, N(5)-Carbamoyl-DL-ornithine, DL-2-Amino-5-ureidovalerate
Substituent Name L-alpha-amino acid, Amino fatty acid, Fatty acyl, Fatty acid, Urea, Monocarboxylic acid or derivatives, Carboxylic acid, Hydrocarbon derivative, Primary amine, Organooxygen compound, Organonitrogen compound, Primary aliphatic amine, Carbonyl group, Amine, Aliphatic acyclic compound
Compound Name Citrulline, (+/-)-
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 175.096
Formal Charge 0.0
Monoisotopic Mass 175.096
Hydrogen Bond Acceptor Count 4.0
Molecular Weight 175.19
Covalent Unit Count 1.0
Total Atom Stereocenter Count 1.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aliphatic acyclic compounds
Esol 1.4795344000000004
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)
Smiles C(CC(C(=O)O)N)CNC(=O)N
Defined Bond Stereocenter Count 0.0
Taxonomy Direct Parent Alpha amino acids

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