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Citrullin

Citrulline

HCID 9750
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Grundinformationen

CAS
372-75-8
Standard-SMILES
NC(=O)NCCC[C@H](N)C(=O)O
InChIKey
RHGKLRLOHDJJDR-BYPYZUCNSA-N
Summenformel
C6H13N3O3
Durchschnittliche Molmasse
175,19 g/mol
Monoisotopische Masse
175,09569129

Namen und Bezeichner

Bevorzugter Name
Citrulline
IUPAC
(2S)-2-amino-5-(carbamoylamino)pentanoic acid
Lokaler Name
Citrullin
Englischer Name
L-Citrulline
Summenformel
C6H13N3O3
Molmasse
175.19

Namen und Synonyme

L-citrullinecitrulline372-75-8delta-UreidonorvalineSitrullineN5-Carbamoyl-L-ornithine(S)-2-Amino-5-ureidopentanoic acidL-CytrullineN5-(Aminocarbonyl)-L-ornithineCitrulline, L-N(delta)-CarbamylornithineN5-(Aminocarbonyl)ornithine
Weitere Namen anzeigen
H-CIT-OHL-CITRULINEL-CITL-Cit-OHCit-OHL-(+)-CITRULLINEL-Citrullin
L-2-Amino-5-ureidovaleric acidN5-carbamoylornithinealpha-Amino-delta-ureidovaleric acid(2S)-2-amino-5-(carbamoylamino)pentanoic acidL-Ornithine, N5-(aminocarbonyl)-2-Amino-5-ureidovaleric acid29VT07BGDA2-Amino-5-uredovaleric acid

Datenbank-Bezeichner

CAS
372-75-8
PubChem CID
9750
DTXSID
DTXSID80883373
ChEMBL
CHEMBL444814
ChEBI
CHEBI:16349
UNII
29VT07BGDA
EC Number
206-759-6
Nikkaji
J5.711H

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-4,3
Polarare Oberfläche (TPSA)
118 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
5
Schwere Atome
12
Formalladung
0
Komplexität
171

Experimentelle und physikochemische Eigenschaften

LogP · 2 Einträge

-3.19

-3.19

Solubility · 2 Einträge

200

212 mg/mL

Melting Point · 2 Einträge

235.5

235.5 °C

Physical DescriptionSolid
Dissociation Constants2.43 (at 25 °C)
Collision Cross Section · 5 Einträge

138 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

132 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]

135.4 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];137.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)];139.4 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

139.51 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

135.5 Ų [M-H]-;139.2 Ų [M+Na]+;137.7 Ų [M+H]+

Physikochemische Eigenschaften

Schmelzpunkt
214 °C · 214 °C
Siedepunkt
306.48 °C · 306.48°C (rough estimate)
Dichte
1.2919 · 1.2919 (rough estimate)
Brechungsindex
26 ° · 26 ° (C=8, 6mol/L HCl)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit
Aqueous Acid (Sparingly). Water (Slightly)
Aggregatzustand
Crystals or Crystalline Powder
pka
2.43 · 2.43(at 25℃)
Farbe
White
Geruch (Odor)
Odorless
Wasserlöslichkeit
200 g/L · 200 g/L (20 ºC)
Merck
14 · 14,2331
BRN
6055157 · 6055157
Major Application
detection
Kosmetik-Inhaltsstoffe Funktionen
SKIN CONDITIONING
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
SMILES
N[C@@H](CCCNC(N)=O)C(O)=O
LogP
-3.19 · -3.190
CAS Datenbank
372 · 372-75-8(CAS DataBase Reference)
EPA chemische Informationen
5 · L-Ornithine, N5-(aminocarbonyl)- (372-75-8)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 14.5% (10 of 69) of reports.

Warning

H315 (85.5%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (85.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 69 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 10 of 69 reports by companies.;There are 2 notifications provided by 59 of 69 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: L-Ornithine, N5-(aminocarbonyl)-

L-Ornithine, N5-(aminocarbonyl)-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazard Classes and CategoriesSkin Irrit. 2 (85.5%);Eye Irrit. 2A (85.5%)

Toxikologische Informationen

Toxicity Summary · 1 Eintrag

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. <br/><br/>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. <br/><br/>All the nitric oxide synthases use NADPH (reduced nicotinamide adenine dinucleotide phosphate) and oxygen (O<sub>2</sub>) 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. <i>In vitro</i> studies of NOS indicate that the Km of the enzyme for L-arginine is in the

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Regulatorische Informationen

Regulatory Information · 2 Einträge

Chemical: L-Ornithine, N5-(aminocarbonyl)-

L-Ornithine, N5-(aminocarbonyl)-: Does not have an individual approval but may be used under an appropriate group standard

Sicherheitsdaten

wgk
3
tsca
TSCA listed
hs_code
29241900
risk_code
36/37/38
hazard_code
Xi
safety_code
24/25-36-26
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

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.

Mechanism of Action · 1 Eintrag

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 (O<sub>2</sub>) 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 co

Tissue LocationsBladder;Epidermis;Fibroblasts;Intestine;Kidney;Liver;Neuron;Placenta;Platelet;Prostate
Cellular LocationsMitochondria
Metabolite Pathways · 1 Eintrag

Arginine and proline metabolism;Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency);Argininemia;Argininosuccinic Aciduria;Aspartate Metabolism;Canavan Disease;Carbamoyl Phosphate Synthetase Deficiency;Citrullinemia Type I;Creatine deficiency, guanidinoacetate methyltransferase deficiency;Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency);Total 21 pathways, visit the HMDB page for details

Verwendung und Herstellung

UsesUsed for nutritional supplementation, also for treating dietary shortage or imbalance.
Household ProductsInformation on 1 consumer products that contain Citrulline in the following categories is provided:;• Personal Care
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing InformationL-Ornithine, N5-(aminocarbonyl)-: ACTIVE

Anwendungen

VerwendenAn amino acid, L-Citrulline can be used in the treatment of asthenia and as an essential intermediate in the biosynthesis of nitric oxide.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

HydroxideArginin

Nachgelagerte Produkte

H-Lys(Alloc)-OHMC-Val-Cit-PABFMoc-Val-Cit-PABFMoc-Val-Cit-PAB-PNPMc-Val-Cit-PABC-PNP

Zugehörige Reaktionen

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