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시트룰린

Citrulline

HCID 9750
새 노트새 반응견적 요청하기
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기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
372-75-8
표준 SMILES
NC(=O)NCCC[C@H](N)C(=O)O
InChIKey
RHGKLRLOHDJJDR-BYPYZUCNSA-N
분자식
C6H13N3O3
평균 분자량
175.19 g/mol
단동위원소 질량
175.09569129

이름 및 식별자

우선 이름
Citrulline
IUPAC
(2S)-2-amino-5-(carbamoylamino)pentanoic acid
현지명
시트룰린
영어명
L-Citrulline
분자식
C6H13N3O3
분자량
175.19

이름 및 동의어

L-citrullinecitrulline372-75-8delta-UreidonorvalineSitrullineN5-Carbamoyl-L-ornithine(S)-2-Amino-5-ureidopentanoic acidL-CytrullineN5-(Aminocarbonyl)-L-ornithineCitrulline, L-N(delta)-CarbamylornithineN5-(Aminocarbonyl)ornithine
이름 더 보기
L-(+)-시트룰린L-시트룰린시트룰린H-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

데이터베이스 식별자

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

물성

구조 계산 물성보충 중

XLogP
-4.3
극성 표면적
118 Ų
수소 결합 공여자 수
4
수소 결합 수용자 수
4
회전 가능 결합 수
5
무거운 원자 수
12
형식 전하
0
복잡도
171

실험 및 물리화학적 성질

LogP · 2건

-3.19

-3.19

Solubility · 2건

200

212 mg/mL

Melting Point · 2건

235.5

235.5 °C

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

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]+

물리화학적 성질

녹는점
214 °C · 214 °C
끓는 점
306.48 °C · 306.48°C (rough estimate)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

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.

유해성 정보

Regulatory Information · 2건

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%)

독성 정보

Toxicity Summary · 1건

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

화학 및 산업

약리 정보

Pharmacodynamics · 1건

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 · 1건

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

관련 반응

28건
반응 기록 만들기
HRID 8741 반응식
HRID 8741반응물로uspto-grants-2006_08
HRID 397250 반응식
HRID 397250반응물로uspto-grants-2003_08
HRID 422898 반응식
HRID 422898생성물로uspto-grants-2012_01
HRID 438007 반응식
HRID 438007반응물로uspto-grants-1977_06
HRID 438011 반응식
HRID 438011반응물로uspto-grants-1977_06
HRID 438013 반응식
HRID 438013반응물로uspto-grants-1977_06
HRID 504077 반응식
HRID 504077반응물로uspto-grants-2010_08
HRID 567633 반응식
HRID 567633반응물로uspto-grants-2001_01
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화합물 노트

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이 페이지에서기본 정보이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
더보기
새 노트새 반응견적 요청하기
밀도
1.2919 · 1.2919 (rough estimate)
굴절률
26 ° · 26 ° (C=8, 6mol/L HCl)
저장 조건
Keep in dark place,Sealed in dry,Room Temperature
용해도
수성 산(드물게). 물(약간 용해됨)
물리적 상태
결정 또는 결정성 분말
산도 계수 (pKa)
2.43 · 2.43(at 25℃)
색상
하얀색
냄새
냄새 없는
수용성
200 g/L · 200g/L(20℃)
Merck
14 · 14,2331
BRN
6055157 · 6055157
주요 응용
발각
화장품 원료 기능
피부 컨디셔닝
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
EPA
5 · L-Ornithine, N5-(aminocarbonyl)- (372-75-8)

화학적 성질

White powder

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

규제 정보

Regulatory Information · 2건

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

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

안전 데이터

wgk
3
tsca
TSCA listed
HS 번호
29241900
risk_code
36/37/38
hazard_code
Xi
safety_code
24/25-36-26
스토리지 클래스
11 - Combustible Solids
Tissue LocationsBladder;Epidermis;Fibroblasts;Intestine;Kidney;Liver;Neuron;Placenta;Platelet;Prostate
Cellular LocationsMitochondria
Metabolite Pathways · 1건

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

용도 및 제조

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

응용 분야

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

상·하류 제품 정보

상류 원료

HydroxideL-(+)-아르기닌

하류 제품

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