FComEx: Phosphocreatine (PC000641)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:44 UTC

Update date

2017-01-19 02:36:31 UTC

FoodComEx ID

PC000641

FoodDB Record

FDB022665

Chemical Information

Name

Phosphocreatine

Description

Phosphocreatine undergoes irreversible cyclization and dehydration to form creatinine at a fractional rate of 0.026 per day, thus forming approximately 2 g creatinine/day in an adult male. This is the amount of creatine that must be provided either from dietary sources or by endogenous synthesis to maintain the body pool of (creatine and) phosphocreatine. Creatine is an amino acid that plays a vital role as phosphocreatine in regenerating adenosine triphosphate in skeletal muscle to energize muscle contraction. Creatine is phosphorylated to phosphocreatine in muscle in a reaction that is catalyzed by the enzyme creatine kinase. This enzyme is in highest concentration in muscle and nerve. Oral administration increases muscle stores. During the past decade, creatine has assumed prominence as an ergogenic (and legal) aid for professional and elite athletes. Most (~ 95%) of the total body creatine-phosphocreatine pool is in muscle (more in skeletal muscle than in smooth muscle) and amounts to 120 g (or 925 mmol) in a 70 kg adult male. Approximately 60-67% of the content in resting muscle is in the phosphorylated form. This generates enough ATP at the myofibrillar apparatus to power about 4 seconds of muscle contraction in exercise. Phosphocreatine reacts with ADP to yield ATP and creatine; the reversible reaction is catalyzed by creatine kinase. phosphocreatine is the chief store of high-energy phosphates in muscle. Thus, this reaction, which permits the rephosphorylation of ADP to ATP, is the immediate source of energy in muscle contraction. During rest, metabolic processes regenerate phosphocreatine stores. In normal muscle, ATP that is broken down to ADP is immediately rephosphorylated to ATP. Thus, phosphocreatine serves as a reservoir of ATP-synthesizing potential. phosphocreatine is the only fuel available to precipitously regenerate ATP during episodes of rapid fluctuations in demand. The availability of phosphocreatine likely limits muscle performance during brief, high-power exercise, i.e., maximal exercise of short duration. With near maximal isometric contraction, the rate of utilization of phosphocreatine declines after 1-2 seconds of contraction, prior to the glycolysis peak at approximately 3 seconds. (PMID: 10079702, Nutr Rev. 1999 Feb;57(2):45-50.) [HMDB]

CAS Number

67-07-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
{[imino(onoamino)methyl](methyl)amino}acetate	Generator
{[imino(onoamino)methyl](methyl)amino}acetic acid	ChEBI
Creatine ate	ChEBI
Creatine ic acid	ChEBI
Creatine phosphate	hmdb
Creatine phosphic acid	hmdb
Creatine-ate	HMDB
creatine-P	hmdb
creatine-phosphate	hmdb
Creatineoric acid	HMDB
Creatinephosphoric acid	hmdb
N-(N-Onoamido)sarcosine	ChEBI
N-(Onoamidino)-sarcosine	HMDB
N-(Onoamidino)sarcosine	ChEBI
N-(phosphonoamidino)-Sarcosine	hmdb
N-(Phosphonoamidino)sarcosine	hmdb
N-[Imino(onoamino)methyl]-N-methyl-glycine	HMDB
N-[imino(phosphonoamino)methyl]-N-methyl-Glycine	hmdb
N-Ocreatine	ChEBI
N-Orocreatine	HMDB
N-Orylcreatine	ChEBI
N-phosphocreatine	hmdb
N-Phosphorocreatine	hmdb
N-Phosphorylcreatine	hmdb
N(Omega)-onocreatine	ChEBI
neo-ton	hmdb
Ocreatine	ChEBI
Orylcreatine	ChEBI
P-creatine	hmdb
phosphocreatine	hmdb
phosphorylcreatine	hmdb

Chemical Formula

C4H10N3O5P

IUPAC name

2-(N-methyl-N'-phosphonocarbamimidamido)acetic acid

InChI Identifier

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)

InChI Key

DRBBFCLWYRJSJZ-UHFFFAOYSA-N

Isomeric SMILES

CN(CC(O)=O)C(=N)NP(O)(O)=O

Average Molecular Weight

211.1131

Monoisotopic Molecular Weight

211.035806957

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents