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Namespace Prefixes

Prefix	IRI
n12	http://linked.opendata.cz/resource/drugbank/drug/DB00155/identifier/pubchem-substance/
n2	http://linked.opendata.cz/resource/drugbank/drug/
dcterms	http://purl.org/dc/terms/
n21	http://linked.opendata.cz/resource/drugbank/drug/DB00155/identifier/drugbank/
n18	http://linked.opendata.cz/resource/drugbank/drug/DB00155/identifier/iuphar/
n15	http://linked.opendata.cz/resource/drugbank/company/
n17	http://linked.opendata.cz/resource/drugbank/drug/DB00155/identifier/guide-to-pharmacology/
n10	http://bio2rdf.org/drugbank:
n19	http://linked.opendata.cz/resource/drugbank/drug/DB00155/identifier/chemspider/
n16	http://linked.opendata.cz/resource/drugbank/drug/DB00155/identifier/chebi/
adms	http://www.w3.org/ns/adms#
n5	http://wifo5-03.informatik.uni-mannheim.de/drugbank/resource/drugs/
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owl	http://www.w3.org/2002/07/owl#
n3	http://linked.opendata.cz/ontology/drugbank/
n9	http://linked.opendata.cz/resource/drugbank/drug/DB00155/identifier/pharmgkb/
n6	http://linked.opendata.cz/resource/drugbank/property/
n14	http://linked.opendata.cz/resource/drugbank/drug/DB00155/identifier/pdb/
n13	http://linked.opendata.cz/resource/drugbank/drug/DB00155/identifier/kegg-compound/
xsdh	http://www.w3.org/2001/XMLSchema#
n11	http://linked.opendata.cz/resource/drugbank/drug/DB00155/identifier/pubchem-compound/

Statements

Subject Item: n2:DB00155
rdf:type: n3:Drug
n3: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.
n3:group: nutraceutical approved
n3:indication: Used for nutritional supplementation, also for treating dietary shortage or imbalance.
owl:sameAs: n5:DB00155 n10:DB00155
dcterms:title: L-Citrulline
adms:identifier: n9:PA164747225 n11:9750 n12:46506583 n13:C00327 n14:CIR n16:16349 n17:722 n18:722 n19:9367 n21:DB00155
n3:mechanismOfAction: L-citrulline is converted to L-arginine by argininosuccinate synthase. L-arginine is in turn responsible for citrulline's therapeutic affects. Many of L-arginine's activities, including its possible anti-atherogenic actions, may be accounted for by its role as the precursor to nitric oxide or NO. NO is produced by all tissues of the body and plays very important roles in the cardiovascular system, immune system and nervous system. NO is formed from L-arginine via the enzyme nitric oxide synthase or synthetase (NOS), and the effects of NO are mainly mediated by 3',5' -cyclic guanylate or cyclic GMP. NO activates the enzyme guanylate cyclase, which catalyzes the synthesis of cyclic GMP from guanosine triphosphate or GTP. Cyclic GMP is converted to guanylic acid via the enzyme cyclic GMP phosphodiesterase. NOS is a heme-containing enzyme with some sequences similar to cytochrome P-450 reductase. Several isoforms of NOS exist, two of which are constitutive and one of which is inducible by immunological stimuli. The constitutive NOS found in the vascular endothelium is designated eNOS and that present in the brain, spinal cord and peripheral nervous system is designated nNOS. The form of NOS induced by immunological or inflammatory stimuli is known as iNOS. iNOS may be expressed constitutively in select tissues such as lung epithelium. All the nitric oxide synthases use NADPH (reduced nicotinamide adenine dinucleotide phosphate) and oxygen (O2) as cosubstrates, as well as the cofactors FAD (flavin adenine dinucleotide), FMN (flavin mononucleotide), tetrahydrobiopterin and heme. Interestingly, ascorbic acid appears to enhance NOS activity by increasing intracellular tetrahydrobiopterin. eNOS and nNOS synthesize NO in response to an increased concentration of calcium ions or in some cases in response to calcium-independent stimuli, such as shear stress. In vitro studies of NOS indicate that the Km of the enzyme for L-arginine is in the micromolar range. The concentration of L-arginine in endothelial cells, as well as in other cells, and in plasma is in the millimolar range. What this means is that, under physiological conditions, NOS is saturated with its L-arginine substrate. In other words, L-arginine would not be expected to be rate-limiting for the enzyme, and it would not appear that supraphysiological levels of L-arginine which could occur with oral supplementation of the amino acid would make any difference with regard to NO production. The reaction would appear to have reached its maximum level. However, in vivo studies have demonstrated that, under certain conditions, e.g. hypercholesterolemia, L-arginine could enhance endothelial-dependent vasodilation and NO production.
n3:packager: n15:271B4CFE-363D-11E5-9242-09173F13E4C5
n3:synonym: α-amino-δ-ureidovaleric acid N(5)-(Aminocarbonyl)-L-ornithine delta-Ureidonorvaline N5-Carbamoyl-L-ornithine alpha-amino-delta-Ureidovaleric acid N5-(Aminocarbonyl)ornithine 2-Amino-5-ureidovaleric acid Cit N(delta)-Carbamylornithine Citrulline δ-ureidonorvaline N5-carbamoylornithine L-Citrulline L-2-Amino-5-ureidovaleric acid (S)-2-Amino-5-ureidopentanoic acid
n3:synthesisReference: Hua Bai, Peijie Yang, Zhengjie Chen, Chongyan Xu, Zhaorul Li, Zigang Zhao, Luyan Jiang, Zongyi Yang, Jiang Li, "PROCESSES FOR THE PRODUCTION OF L-CITRULLINE." U.S. Patent US20090142813, issued June 04, 2009.
n3:IUPAC-Name: n6:271B4D04-363D-11E5-9242-09173F13E4C5
n3:InChI: n6:271B4D0A-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula: n6:271B4D09-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight: n6:271B4D06-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight: n6:271B4D07-363D-11E5-9242-09173F13E4C5
n3:SMILES: n6:271B4D08-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility: n6:271B4D1A-363D-11E5-9242-09173F13E4C5 n6:271B4D02-363D-11E5-9242-09173F13E4C5
n3:logP: n6:271B4D1C-363D-11E5-9242-09173F13E4C5 n6:271B4D00-363D-11E5-9242-09173F13E4C5 n6:271B4D03-363D-11E5-9242-09173F13E4C5
n3:logS: n6:271B4D01-363D-11E5-9242-09173F13E4C5
n3:pKa: n6:271B4D1D-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count: n6:271B4D10-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count: n6:271B4D11-363D-11E5-9242-09173F13E4C5
n3:InChIKey: n6:271B4D0B-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-: n6:271B4D0C-363D-11E5-9242-09173F13E4C5
n3:Polarizability: n6:271B4D0E-363D-11E5-9242-09173F13E4C5
n3:Refractivity: n6:271B4D0D-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count: n6:271B4D0F-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism: Humans and other mammals
n3:casRegistryNumber: 372-75-8
n3:category
n3:containedIn: n20:271B4CFF-363D-11E5-9242-09173F13E4C5
n3:Bioavailability: n6:271B4D16-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter: n6:271B4D18-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule: n6:271B4D19-363D-11E5-9242-09173F13E4C5
n3:Melting-Point: n6:271B4D1B-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings: n6:271B4D15-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge: n6:271B4D14-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five: n6:271B4D17-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name: n6:271B4D05-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-: n6:271B4D12-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-: n6:271B4D13-363D-11E5-9242-09173F13E4C5