Common NameN-phosphocreatine
DescriptionPhosphocreatine, also known as creatine phosphate (CP) or PCr (Pcr), is a phosphorylated creatine molecule that serves as a rapidly mobilizable reserve of high-energy phosphates in skeletal muscle, myocardium and the brain to recycle adenosine triphosphate, the energy currency of the cell. 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 ).
Structure
Molecular FormulaC4H10N3O5P
Average Mass211.11310
Monoisotopic Mass211.03581
IUPAC Name2-(1-methyl-3-phosphonocarbamimidamido)acetic acid
Traditional NamePhosphocreatine
CAS Registry Number67-07-2
SMILESCN(CC(=O)[O-])C(=[NH2+])NP(=O)([O-])[O-]
InChI IdentifierInChI=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 KeyDRBBFCLWYRJSJZ-UHFFFAOYSA-N
CHEBI IDCHEBI:58092
HMDB IDHMDB0001511
Pathways
NameSMPDB/PathBank
Arginine and proline metabolism
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)
Prolidase Deficiency (PD)
Prolinemia Type II
Hyperprolinemia Type II
Hyperprolinemia Type I
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)
Ornithine Aminotransferase Deficiency (OAT Deficiency)
Creatine deficiency, guanidinoacetate methyltransferase deficiency
Hyperornithinemia with gyrate atrophy (HOGA)
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]
L-arginine:glycine amidinotransferase deficiency
StateSolid
Water Solubility3.52e+00 g/l
logP-2.01
logS-1.78
pKa (Strongest Acidic)-1.10
pKa (Strongest Basic)11.57
Hydrogen Acceptor Count7
Hydrogen Donor Count5
Polar Surface Area133.95 Ų
Rotatable Bond Count3
Physiological Charge-2
Formal Charge0
Refractivity53.18 m³·mol⁻¹
Polarizability16.82

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