Human Metabolome Database Version 3.5

Showing metabocard for Phosphocreatine (HMDB01511)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:32:02 -0600
HMDB ID HMDB01511
Secondary Accession Numbers None
Metabolite Identification
Common 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 Link_out, Nutr Rev. 1999 Feb;57(2):45-50.).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C4H10N3O5P
Average Molecular Weight 211.1131
Monoisotopic Molecular Weight 211.035806957
IUPAC Name 2-(1-methyl-3-phosphonocarbamimidamido)acetic acid
Traditional IUPAC Name phosphocreatine
CAS Registry Number 67-07-2
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 Key DRBBFCLWYRJSJZ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • phosphoamino acid(ChEBI)
Substituents
  • Carboxylic Acid
  • Guanidine
  • Organic Hypophosphite
  • Organic Phosphoric Acid Amide
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Arginine and proline metabolism
Application Not Available
Cellular locations
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.52 g/L ALOGPS
LogP -2.01 ALOGPS
LogP -2.3 ChemAxon
LogS -1.78 ALOGPS
pKa (strongest acidic) -1.1 ChemAxon
pKa (strongest basic) 11.57 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 133.95 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 53.18 ChemAxon
Polarizability 16.82 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
MS/MS Spectrum LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
Biofluid Locations
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Fibroblasts
  • Neuron
  • Testes
  • Kidney
  • Brain
  • Skin
  • Adipose Tissue
  • Basal Ganglia
  • Hippocampus
Pathways
Name SMPDB Link KEGG Link
Arginine and Proline Metabolism SMP00020 map00330 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022665
KNApSAcK ID Not Available
Chemspider ID 567 Link_out
KEGG Compound ID C02305 Link_out
BioCyc ID CREATINE-P Link_out
BiGG ID 1594794 Link_out
Wikipedia Link Creatine phosphate Link_out
NuGOwiki Link HMDB01511 Link_out
Metagene Link HMDB01511 Link_out
METLIN ID 6288 Link_out
PubChem Compound 587 Link_out
PDB ID Not Available
ChEBI ID 17287 Link_out
References
Synthesis Reference Hou, 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out
  12. 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 Link_out
  13. 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 Link_out
  14. Hargreaves M: Skeletal muscle metabolism during exercise in humans. Clin Exp Pharmacol Physiol. 2000 Mar;27(3):225-8. Pubmed: 10744352 Link_out
  15. 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 Link_out
  16. 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 Link_out
  17. 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 Link_out
  18. 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 Link_out
  19. 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 Link_out
  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 Link_out
  21. Feldman EB: Creatine: a dietary supplement and ergogenic aid. Nutr Rev. 1999 Feb;57(2):45-50. Pubmed: 10079702 Link_out

Enzymes
Name: Creatine kinase S-type, mitochondrial
Reactions:
Adenosine triphosphate + Creatine unknown ADP + Phosphocreatine details
Gene Name: CKMT2
Uniprot ID: P17540 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Creatine kinase B-type
Reactions:
Adenosine triphosphate + Creatine unknown ADP + Phosphocreatine details
Gene Name: CKB
Uniprot ID: P12277 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Creatine kinase U-type, mitochondrial
Reactions:
Adenosine triphosphate + Creatine unknown ADP + Phosphocreatine details
Gene Name: CKMT1A
Uniprot ID: P12532 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Creatine kinase M-type
Reactions:
Adenosine triphosphate + Creatine unknown ADP + Phosphocreatine details
Gene Name: CKM
Uniprot ID: P06732 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA