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N-methyl-N-(N-phosphonocarbamimidoyl)glycine

HCID 587
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
67-07-2
표준 SMILES
CN(CC(=O)O)C(N)=NP(=O)(O)O
InChIKey
DRBBFCLWYRJSJZ-UHFFFAOYSA-N
분자식
C4H10N3O5P
평균 분자량
211.11 g/mol
단동위원소 질량
211.03580743

개요

Phosphocreatine - or creatine phosphate - is the phosphorylated form of creatine. It is primarily found endogenously in the skeletal muscles of vertebrates where it serves a critical role as a rapidly acting energy buffer for muscle cell actions like contractions via its ability to regenerate adenosine triphosphate (ATP) from adenosine diphosphate (ADP).

이름 및 식별자

우선 이름
N-methyl-N-(N-phosphonocarbamimidoyl)glycine
IUPAC
2-[methyl-(N'-phosphonocarbamimidoyl)amino]acetic acid
영어명
Creatine phosphate
분자식
C4H10N3O5P
분자량
211.11

이름 및 동의어

Creatine Phosphate (Phosphocreatine), >85%N-methyl-N-(N-phosphonocarbamimidoyl)glycine2-(3-methyl-1-phosphonocarbamimidamido)acetic acid2-(1-Methyl-3-phosphonoguanidino)acetic acidC4H10N3O5PCreatinephosphateMFCD00152044Creatine phosphate; Creatinephosphoric acidSCHEMBL65424SCHEMBL65425SCHEMBL2124030SCHEMBL24116748
이름 더 보기
phosphocreatineGlycine, N-[imino(phosphonoamino)methyl]-N-methyl-Neotonphosphagenn-phosphocreatineCREATINE PHOSPHATEN-PhosphorocreatineCreatine phosphate 90%Creatine phosphoric acid
Creatine Phosphate; PhosphocreatineFC149077NS00041187H57884Q1984607

데이터베이스 식별자

CAS
67-07-2
PubChem CID
587

물성

구조 계산 물성

XLogP
-2.6
극성 표면적
136 Ų
수소 결합 공여자 수
4
수소 결합 수용자 수
6
회전 가능 결합 수
4
무거운 원자 수
13
형식 전하
0
복잡도
271

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
Boiling Point449.1±47.0 °C at 760 mmHg
Melting Point194-195 °C
Physical DescriptionSolid
Collision Cross Section · 4건

142.8 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

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

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

144.8 Ų [M+H]+

물리화학적 성질

녹는점
175 oC · >175oC (dec.)
끓는 점
449.1 · 449.1±47.0 °C(Predicted)
밀도
1.83 · 1.83±0.1 g/cm3(Predicted)
저장 조건
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
용해도
에 용해됨물
산도 계수 (pKa)
4.7 · pKa 4.7± 0.01(H2O,t =25)(Approximate)
물리적 상태
고체
색상
흰색에서 황백색까지
안정성
흡습성
InChI
InChI=1S/C4H10N3O5P/c1-7(2-3(8)9)4(5)6-13(10,11)12/h2H2,1H3,(H,8,9)(H4,5,6,10,11,12)
InChIKey
DRBBFCLWYRJSJZ-UHFFFAOYSA-N
SMILES
C(O)(=O)CN(C(=N)NP(O)(O)=O)C
EPA
Glycine, N-[imino(phosphonoamino)methyl]-N-methyl- (67-07-2)

안전 및 규제

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

안전 데이터

tsca
TSCA listed

화학 및 산업

약리 정보

Pharmacodynamics · 1건

Creatine is a naturally occurring chemical within the body and is primarily stored in skeletal muscle in both free and phosphorylated forms. Phosphocreatine is the name given to the phosphorylated form of creatine. Additionally, phosphocreatine can also be found in other areas of the body like the kidneys, liver, and brain. In fact, most *in vivo* synthesis of creatine occurs in the liver where amidine groups from arginine are transfered to glycine with the help of the glycine transaminidase enzyme to form guanidinoacetic acid. This acid is then methylated with the methyl group of S-adenosylmethionine via guanidinoacetate methyltransferase to generate creatine. The synthesized creatine is transported to storage sites in skeletal muscle via the bloodstream. The phosphorylation of creatine is reversible in both a forwards and backwards reaction. That is, while phosphocreatine is capable of anaerobically donating a phosphate group to adenosine diphosphate (ADP) to regenerate ATP, at the same time excess ATP can be dephosphorylated during periods of low muscle activity to convert creatine to phosphocreatine. This dual activity in synthesizing phosphocreatine from excess levels of ATP during rest and use of phosphocreatine to regenerate ATP during high activity demonstrates the crucial utility of phosphocreatine in acting as an energy buffer in body mucle cells. Phosphocreatine's fast regeneration of ATP is considered a coupled reaction - in essence, the energy released from transferring a donating a phosphate group from phosphocreatine is used to regenerate ATP. Phosphocreatine consequently plays an essential role in body tissues that have high, fluctuating energy requirments like muscle and brain tissues.

Mechanism of Action · 1건

Adenosine triphosphate (ATP) is the primary source of chemical energy that body muscles use to perform contractions. During such contraction processes, ATP molecules are depleted as they undergo hydrolysis reactions and become adenosine diphosphate (ADP). To maintain homeostasis in muscle activity, the ATP supply of muscles must be regenerated regularly. Phosphocreatine occurs naturally within the body and is capable of regenerating ATP by transferring a high-energy phosphate from itself to ADP, resulting in the formation of ATP and creatine. This kind of regeneration of ATP with phosphocreatine typically occurs within seconds of intense muscular or neuronal effort, acting as a quickly accessible reserve of high-energy phosphates for the recycling of ATP in body muscle tissues. ATP recycling from phosphocreatine is in fact known as the quickest form of ATP regeneration.

Absorption, Distribution and Excretion · 1건

Phosphocreatine is eliminated renally. The end result of creatine degredation is the product creatinine, which enters the bloodstream from its storage sites in body muscle. When creatinine enters the renal parenchyma it is filtered in the renal glomerulus to be excreted in the urine.

Tissue LocationsAdipose Tissue
Cellular LocationsMitochondria
Metabolite PathwaysArginine and proline metabolism

응용 분야

용도Phosphocreatine used in the synthesis of hydroxypatite nanorod/nanosheets. Phosphocreatine is used in the treatment of heart and brain ischemia.

공급사100 곳

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