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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:32:02 UTC
HMDB IDHMDB01511
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhosphocreatine
DescriptionPhosphocreatine 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.).
Structure
Thumb
Synonyms
  1. Creatine phosphate
  2. Creatine-P
  3. Creatine-phosphate
  4. Creatinephosphoric acid
  5. N-(Phosphonoamidino)-Sarcosine
  6. N-(Phosphonoamidino)sarcosine
  7. N-Phosphocreatine
  8. N-Phosphorocreatine
  9. N-Phosphorylcreatine
  10. N-[Imino(phosphonoamino)methyl]-N-methyl-Glycine
  11. Neo-ton
  12. P-Creatine
  13. Phosphocreatine
  14. Phosphorylcreatine
Chemical FormulaC4H10N3O5P
Average Molecular Weight211.1131
Monoisotopic Molecular Weight211.035806957
IUPAC Name2-(1-methyl-3-phosphonocarbamimidamido)acetic acid
Traditional IUPAC Namephosphocreatine
CAS Registry Number67-07-2
SMILES
CN(CC(O)=O)C(=N)NP(O)(O)=O
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 KeyDRBBFCLWYRJSJZ-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • phosphoamino acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Guanidine
  • Organic Hypophosphite
  • Organic Phosphoric Acid Amide
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Arginine and proline metabolism
ApplicationNot Available
Cellular locations
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility3.52 g/LALOGPS
logP-2ALOGPS
logP-2.3ChemAxon
logS-1.8ALOGPS
pKa (strongest acidic)-1.1ChemAxon
pKa (strongest basic)11.57ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count7ChemAxon
hydrogen donor count5ChemAxon
polar surface area133.95ChemAxon
rotatable bond count3ChemAxon
refractivity53.18ChemAxon
polarizability16.82ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Urine
Tissue Location
  • Adipose Tissue
  • Basal Ganglia
  • Brain
  • Fibroblasts
  • Hippocampus
  • Kidney
  • Muscle
  • Neuron
  • Skeletal Muscle
  • Skin
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020map00330
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022665
KNApSAcK IDNot Available
Chemspider ID567
KEGG Compound IDC02305
BioCyc IDCREATINE-P
BiGG ID1594794
Wikipedia LinkCreatine phosphate
NuGOwiki LinkHMDB01511
Metagene LinkHMDB01511
METLIN ID6288
PubChem Compound587
PDB IDNot Available
ChEBI ID17287
References
Synthesis ReferenceHou, Lixiang. Method for producing creatine phosphate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2004), 7 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pastoris O, Dossena M, Foppa P, Catapano M, Arbustini E, Bellini O, Dal Bello B, Minzioni G, Ceriana P, Barzaghi N: Effect of L-carnitine on myocardial metabolism: results of a balanced, placebo-controlled, double-blind study in patients undergoing open heart surgery. Pharmacol Res. 1998 Feb;37(2):115-22. Pubmed: 9572066
  2. Schmidt A, Marescau B, Boehm EA, Renema WK, Peco R, Das A, Steinfeld R, Chan S, Wallis J, Davidoff M, Ullrich K, Waldschutz R, Heerschap A, De Deyn PP, Neubauer S, Isbrandt D: Severely altered guanidino compound levels, disturbed body weight homeostasis and impaired fertility in a mouse model of guanidinoacetate N-methyltransferase (GAMT) deficiency. Hum Mol Genet. 2004 May 1;13(9):905-21. Epub 2004 Mar 17. Pubmed: 15028668
  3. Gideon P, Henriksen O, Sperling B, Christiansen P, Olsen TS, Jorgensen HS, Arlien-Soborg P: Early time course of N-acetylaspartate, creatine and phosphocreatine, and compounds containing choline in the brain after acute stroke. A proton magnetic resonance spectroscopy study. Stroke. 1992 Nov;23(11):1566-72. Pubmed: 1440704
  4. Green AL, Hultman E, Macdonald IA, Sewell DA, Greenhaff PL: Carbohydrate ingestion augments skeletal muscle creatine accumulation during creatine supplementation in humans. Am J Physiol. 1996 Nov;271(5 Pt 1):E821-6. Pubmed: 8944667
  5. Skare OC, Skadberg, Wisnes AR: Creatine supplementation improves sprint performance in male sprinters. Scand J Med Sci Sports. 2001 Apr;11(2):96-102. Pubmed: 11252467
  6. Greenhaff PL, Soderlund K, Ren JM, Hultman E: Energy metabolism in single human muscle fibres during intermittent contraction with occluded circulation. J Physiol. 1993 Jan;460:443-53. Pubmed: 8487203
  7. Greiner A, Esterhammer R, Pilav S, Arnold W, Santner W, Neuhauser B, Fraedrich G, Jaschke WR, Schocke MF: High-energy phosphate metabolism in the calf muscle during moderate isotonic exercise under different degrees of cuff compression: a phosphorus 31 magnetic resonance spectroscopy study. J Vasc Surg. 2005 Aug;42(2):259-67. Pubmed: 16102624
  8. Murphy AJ, Watsford ML, Coutts AJ, Richards DA: Effects of creatine supplementation on aerobic power and cardiovascular structure and function. J Sci Med Sport. 2005 Sep;8(3):305-13. Pubmed: 16248471
  9. Braegger CP, Schlattner U, Wallimann T, Utiger A, Frank F, Schaefer B, Heizmann CW, Sennhauser FH: Effects of creatine supplementation in cystic fibrosis: results of a pilot study. J Cyst Fibros. 2003 Dec;2(4):177-82. Pubmed: 15463870
  10. Kemp GJ, Hands LJ, Ramaswami G, Taylor DJ, Nicolaides A, Amato A, Radda GK: Calf muscle mitochondrial and glycogenolytic ATP synthesis in patients with claudication due to peripheral vascular disease analysed using 31P magnetic resonance spectroscopy. Clin Sci (Lond). 1995 Dec;89(6):581-90. Pubmed: 8549076
  11. Taylor DJ, Thompson CH, Kemp GJ, Barnes PR, Sanderson AL, Radda GK, Phillips DI: A relationship between impaired fetal growth and reduced muscle glycolysis revealed by 31P magnetic resonance spectroscopy. Diabetologia. 1995 Oct;38(10):1205-12. Pubmed: 8690173
  12. Ferguson RA, Ball D, Krustrup P, Aagaard P, Kjaer M, Sargeant AJ, Hellsten Y, Bangsbo J: Muscle oxygen uptake and energy turnover during dynamic exercise at different contraction frequencies in humans. J Physiol. 2001 Oct 1;536(Pt 1):261-71. Pubmed: 11579174
  13. Ferguson RA, Krustrup P, Kjaer M, Mohr M, Ball D, Bangsbo J: Effect of temperature on skeletal muscle energy turnover during dynamic knee-extensor exercise in humans. J Appl Physiol. 2006 Jul;101(1):47-52. Epub 2006 Mar 2. Pubmed: 16514001
  14. Duffield R, Dawson B, Goodman C: Energy system contribution to 1500- and 3000-metre track running. J Sports Sci. 2005 Oct;23(10):993-1002. Pubmed: 16194976
  15. Hargreaves M: Skeletal muscle metabolism during exercise in humans. Clin Exp Pharmacol Physiol. 2000 Mar;27(3):225-8. Pubmed: 10744352
  16. Crowther GJ, Kemper WF, Carey MF, Conley KE: Control of glycolysis in contracting skeletal muscle. II. Turning it off. Am J Physiol Endocrinol Metab. 2002 Jan;282(1):E74-9. Pubmed: 11739086
  17. Preen D, Dawson B, Goodman C, Beilby J, Ching S: Creatine supplementation: a comparison of loading and maintenance protocols on creatine uptake by human skeletal muscle. Int J Sport Nutr Exerc Metab. 2003 Mar;13(1):97-111. Pubmed: 12660409
  18. Raymer GH, Marsh GD, Kowalchuk JM, Thompson RT: Metabolic effects of induced alkalosis during progressive forearm exercise to fatigue. J Appl Physiol. 2004 Jun;96(6):2050-6. Epub 2004 Feb 6. Pubmed: 14766777
  19. Krustrup P, Mohr M, Amstrup T, Rysgaard T, Johansen J, Steensberg A, Pedersen PK, Bangsbo J: The yo-yo intermittent recovery test: physiological response, reliability, and validity. Med Sci Sports Exerc. 2003 Apr;35(4):697-705. Pubmed: 12673156
  20. Iyo M, Sekine Y, Mori N: Neuromechanism of developing methamphetamine psychosis: a neuroimaging study. Ann N Y Acad Sci. 2004 Oct;1025:288-95. Pubmed: 15542729
  21. Feldman EB: Creatine: a dietary supplement and ergogenic aid. Nutr Rev. 1999 Feb;57(2):45-50. Pubmed: 10079702

Enzymes

General function:
Involved in kinase activity
Specific function:
Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
Gene Name:
CKMT2
Uniprot ID:
P17540
Molecular weight:
47504.08
Reactions
Adenosine triphosphate + Creatine → ADP + Phosphocreatinedetails
General function:
Involved in kinase activity
Specific function:
Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
Gene Name:
CKB
Uniprot ID:
P12277
Molecular weight:
42643.95
Reactions
Adenosine triphosphate + Creatine → ADP + Phosphocreatinedetails
General function:
Involved in kinase activity
Specific function:
Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
Gene Name:
CKMT1A
Uniprot ID:
P12532
Molecular weight:
47036.3
Reactions
Adenosine triphosphate + Creatine → ADP + Phosphocreatinedetails
General function:
Involved in kinase activity
Specific function:
Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
Gene Name:
CKM
Uniprot ID:
P06732
Molecular weight:
43100.91
Reactions
Adenosine triphosphate + Creatine → ADP + Phosphocreatinedetails