Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:50 UTC
HMDB IDHMDB00064
Secondary Accession NumbersNone
Metabolite Identification
Common NameCreatine
DescriptionCreatine is an amino acid that occurs in vertebrate tissues and in urine. In muscle tissue, creatine generally occurs as phosphocreatine. Creatine is excreted as creatinine in the urine. Creatine functions as part of the cell's energy shuttle. The high energy phosphate group of ATP is transferred to creatine to form phosphocreatine in the following reaction: Cr + ATP <-> PCr + ADP. This reaction is reversibly catalyzed by creatine kinase. In the human body creatine is synthesized mainly in the liver by the use of parts from three different amino acids - arginine, glycine, and methionine. 95% of it is later stored in the skeletal muscles, with the rest in the brain, heart, testes.
Structure
Thumb
Synonyms
  1. ((amino(imino)methyl)(methyl)amino)acetate
  2. ((amino(imino)methyl)(methyl)amino)acetic acid
  3. (alpha-Methylguanido)acetate
  4. (alpha-Methylguanido)acetic acid
  5. Cosmocair C 100
  6. Creatin
  7. Creatine
  8. Creatine hydrate
  9. Kreatin
  10. Krebiozon
  11. Methylguanidoacetate
  12. Methylguanidoacetic acid
  13. N-(Aminoiminomethyl)-N-Methyl-Glycine
  14. N-Methyl-N-guanylglycine
  15. Phosphagen
  16. [[Amino(imino)methyl](methyl)amino]acetate
  17. [[Amino(imino)methyl](methyl)amino]acetic acid
Chemical FormulaC4H9N3O2
Average Molecular Weight131.1332
Monoisotopic Molecular Weight131.069476547
IUPAC Name2-(1-methylcarbamimidamido)acetic acid
Traditional IUPAC Namecreatine
CAS Registry Number57-00-1
SMILES
CN(CC(O)=O)C(N)=N
InChI Identifier
InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)
InChI KeyCVSVTCORWBXHQV-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
  • amino acid zwitterion(ChEBI)
Substituents
  • Carboxylic Acid
  • Guanidine
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Arginine and proline metabolism
  • Component of Glycine, serine and threonine metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point303 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility13.3 mg/mL at 18 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility4.11 g/LALOGPS
logP-1.6ALOGPS
logP-2.9ChemAxon
logS-1.5ALOGPS
pKa (strongest acidic)3.5ChemAxon
pKa (strongest basic)12.43ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area90.41ChemAxon
rotatable bond count2ChemAxon
refractivity42.01ChemAxon
polarizability12.2ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Bladder
  • Brain
  • Epidermis
  • Fibroblasts
  • Heart
  • Intestine
  • Kidney
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020map00330
Glycine and Serine MetabolismSMP00004map00260
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified54.8 +/- 21.0 uMAdult (>18 years old)FemaleNormal
BloodDetected and Quantified30.1 +/- 12.3 uMAdult (>18 years old)MaleNormal
BloodDetected and Quantified84.0 +/- 23.2 uMNewborn (0-30 days old)Not SpecifiedNormal
  • Geigy Scient...
BloodDetected and Quantified53.0 (17.0 - 82.0) uMChildren (1-13 year old)Not SpecifiedNormal
  • Geigy Scient...
BloodDetected and Quantified36.7 +/- 28.3 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified44 +/- 13 uMNot SpecifiedBothNormal
UrineDetected and Quantified113.0 (0.00-654.0) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified113(0-654) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified0.00-404.37 umol/mmol creatinineAdult (>18 years old)BothNormal
  • David F. Put...
UrineDetected and Quantified46 (3-448) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified26.0 (5.0-95.0) umol/mmol creatinineAdult (>18 years old)MaleNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
UrineDetected and Quantified46.0 (9.0-135.0) umol/mmol creatinineAdult (>18 years old)FemaleNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
UrineDetected and Quantified11.30 umol/mmol creatinineAdult (>18 years old)MaleNormal
  • Shaykhutdino...
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified33.8 +/- 37.7 uMAdult (>18 years old)Not SpecifiedHeart Transplant
BloodDetected and Quantified40.3 (28.3-56.6) uMAdult (>18 years old)FemaleCirrhosis
BloodDetected and Quantified25.7 (16.5 - 30.8) uMAdult (>18 years old)MaleCirrhosis
UrineDetected and Quantified37.0 (0.0-197.0) umol/mmol creatinineNot SpecifiedBothLung cancer
UrineDetected and Quantified1540 umol/mmol creatinineAdult (>18 years old)FemaleRhabdomyolysis
Associated Disorders and Diseases
Disease References
Cirrhosis
  • Marescau B, De Deyn PP, Holvoet J, Possemiers I, Nagels G, Saxena V, Mahler C: Guanidino compounds in serum and urine of cirrhotic patients. Metabolism. 1995 May;44(5):584-8. Pubmed: 7752905
Lung Cancer
  • Stretch C, Eastman T, Mandal R, Eisner R, Wishart DS, Mourtzakis M, Prado CM, Damaraju S, Ball RO, Greiner R, Baracos VE: Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach. J Nutr. 2012 Jan;142(1):14-21. doi: 10.3945/jn.111.147751. Epub 2011 Dec 7. Pubmed: 22157537
Rhabdomyolysis
  • Bairaktari E, Seferiadis K, Liamis G, Psihogios N, Tsolas O, Elisaf M: Rhabdomyolysis-related renal tubular damage studied by proton nuclear magnetic resonance spectroscopy of urine. Clin Chem. 2002 Jul;48(7):1106-9. Pubmed: 12089184
Associated OMIM IDs
DrugBank IDDB00148
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB005403
KNApSAcK IDNot Available
Chemspider ID566
KEGG Compound IDC00300
BioCyc IDCREATINE
BiGG ID34543
Wikipedia LinkCreatine
NuGOwiki LinkHMDB00064
Metagene LinkHMDB00064
METLIN ID7
PubChem Compound586
PDB IDCRN
ChEBI ID16919
References
Synthesis ReferenceThalhammer, Franz; Gastner, Thomas. Preparation of creatine, creatine monohydrate and guanidinoacetic acid. Ger. Offen. (2007), 5pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Subramanian A, Gupta A, Saxena S, Gupta A, Kumar R, Nigam A, Kumar R, Mandal SK, Roy R: Proton MR CSF analysis and a new software as predictors for the differentiation of meningitis in children. NMR Biomed. 2005 Jun;18(4):213-25. Pubmed: 15627241
  2. Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. Pubmed: 6321058
  3. Schonberger B: [Overactive bladder--which diagnosis investigations are necessary before initiating primary treatment?] Urologe A. 2003 Jun;42(6):787-92. Epub 2003 Apr 25. Pubmed: 12851769
  4. Mercimek-Mahmutoglu S, Stoeckler-Ipsiroglu S, Adami A, Appleton R, Araujo HC, Duran M, Ensenauer R, Fernandez-Alvarez E, Garcia P, Grolik C, Item CB, Leuzzi V, Marquardt I, Muhl A, Saelke-Kellermann RA, Salomons GS, Schulze A, Surtees R, van der Knaap MS, Vasconcelos R, Verhoeven NM, Vilarinho L, Wilichowski E, Jakobs C: GAMT deficiency: features, treatment, and outcome in an inborn error of creatine synthesis. Neurology. 2006 Aug 8;67(3):480-4. Epub 2006 Jul 19. Pubmed: 16855203
  5. McConell GK, Shinewell J, Stephens TJ, Stathis CG, Canny BJ, Snow RJ: Creatine supplementation reduces muscle inosine monophosphate during endurance exercise in humans. Med Sci Sports Exerc. 2005 Dec;37(12):2054-61. Pubmed: 16331129
  6. McMorris T, Harris RC, Swain J, Corbett J, Collard K, Dyson RJ, Dye L, Hodgson C, Draper N: Effect of creatine supplementation and sleep deprivation, with mild exercise, on cognitive and psychomotor performance, mood state, and plasma concentrations of catecholamines and cortisol. Psychopharmacology (Berl). 2006 Mar;185(1):93-103. Epub 2006 Jan 17. Pubmed: 16416332
  7. Wang PF, McLeish MJ, Kneen MM, Lee G, Kenyon GL: An unusually low pK(a) for Cys282 in the active site of human muscle creatine kinase. Biochemistry. 2001 Oct 2;40(39):11698-705. Pubmed: 11570870
  8. Olsen S, Aagaard P, Kadi F, Tufekovic G, Verney J, Olesen JL, Suetta C, Kjaer M: Creatine supplementation augments the increase in satellite cell and myonuclei number in human skeletal muscle induced by strength training. J Physiol. 2006 Jun 1;573(Pt 2):525-34. Epub 2006 Mar 31. Pubmed: 16581862
  9. Ellington WR: A dimeric creatine kinase from a sponge: implications in terms of phosphagen kinase evolution. Comp Biochem Physiol B Biochem Mol Biol. 2000 May;126(1):1-7. Pubmed: 10825659
  10. Fredericks S, Murray JF, Bewick M, Chang R, Collinson PO, Carter ND, Holt DW: Cardiac troponin T and creatine kinase MB are not increased in exterior oblique muscle of patients with renal failure. Clin Chem. 2001 Jun;47(6):1023-30. Pubmed: 11375287
  11. Jiao YF, Okumiya T, Saibara T, Kudo Y, Sugiura T: Erythrocyte creatine as a marker of excessive erythrocyte destruction due to hypersplenism in patients with liver cirrhosis. Clin Biochem. 2001 Jul;34(5):395-8. Pubmed: 11522277
  12. Nicholson JK, Buckingham MJ, Sadler PJ: High resolution 1H n.m.r. studies of vertebrate blood and plasma. Biochem J. 1983 Jun 1;211(3):605-15. Pubmed: 6411064
  13. Sheth NP, Sennett B, Berns JS: Rhabdomyolysis and acute renal failure following arthroscopic knee surgery in a college football player taking creatine supplements. Clin Nephrol. 2006 Feb;65(2):134-7. Pubmed: 16509464
  14. Jenkins CB, Ghidini A, Spong CY, Eglinton GS, Pezzullo JC, Michejda M: Evaluation of early second trimester maternal serum creatine kinase isoenzyme BB as a marker of poor pregnancy outcome. Fetal Diagn Ther. 1997 Nov-Dec;12(6):356-9. Pubmed: 9475367
  15. Lukaszuk JM, Robertson RJ, Arch JE, Moyna NM: Effect of a defined lacto-ovo-vegetarian diet and oral creatine monohydrate supplementation on plasma creatine concentration. J Strength Cond Res. 2005 Nov;19(4):735-40. Pubmed: 16287366
  16. Preen DB, Dawson BT, Goodman C, Beilby J, Ching S: Comparison of erythrocyte and skeletal muscle creatine accumulation following creatine loading. Int J Sport Nutr Exerc Metab. 2005 Feb;15(1):84-93. Pubmed: 15902992
  17. Poortmans JR, Kumps A, Duez P, Fofonka A, Carpentier A, Francaux M: Effect of oral creatine supplementation on urinary methylamine, formaldehyde, and formate. Med Sci Sports Exerc. 2005 Oct;37(10):1717-20. Pubmed: 16260971
  18. Yoshizumi WM, Tsourounis C: Effects of creatine supplementation on renal function. J Herb Pharmacother. 2004;4(1):1-7. Pubmed: 15273072
  19. Harris RC, Almada AL, Harris DB, Dunnett M, Hespel P: The creatine content of Creatine Serum and the change in the plasma concentration with ingestion of a single dose. J Sports Sci. 2004 Sep;22(9):851-7. Pubmed: 15513279
  20. Mendes RR, Pires I, Oliveira A, Tirapegui J: Effects of creatine supplementation on the performance and body composition of competitive swimmers. J Nutr Biochem. 2004 Aug;15(8):473-8. Pubmed: 15302082
  21. Burke DG, Chilibeck PD, Parise G, Tarnopolsky MA, Candow DG: Effect of alpha-lipoic acid combined with creatine monohydrate on human skeletal muscle creatine and phosphagen concentration. Int J Sport Nutr Exerc Metab. 2003 Sep;13(3):294-302. Pubmed: 14669930
  22. Hultman E, Soderlund K, Timmons JA, Cederblad G, Greenhaff PL: Muscle creatine loading in men. J Appl Physiol (1985). 1996 Jul;81(1):232-7. Pubmed: 8828669
  23. Dangott B, Schultz E, Mozdziak PE: Dietary creatine monohydrate supplementation increases satellite cell mitotic activity during compensatory hypertrophy. Int J Sports Med. 2000 Jan;21(1):13-6. Pubmed: 10683092
  24. Hespel P, Op't Eijnde B, Van Leemputte M, Urso B, Greenhaff PL, Labarque V, Dymarkowski S, Van Hecke P, Richter EA: Oral creatine supplementation facilitates the rehabilitation of disuse atrophy and alters the expression of muscle myogenic factors in humans. J Physiol. 2001 Oct 15;536(Pt 2):625-33. Pubmed: 11600695
  25. Juhn M: Popular sports supplements and ergogenic aids. Sports Med. 2003;33(12):921-39. Pubmed: 12974658

Enzymes

Gene Name:
GAMT
Uniprot ID:
Q14353
Reactions
S-Adenosylmethionine + Guanidoacetic acid unknown S-Adenosylhomocysteine + Creatinedetails
Gene Name:
CKMT2
Uniprot ID:
P17540
Reactions
Adenosine triphosphate + Creatine unknown ADP + Phosphocreatinedetails
Gene Name:
CKB
Uniprot ID:
P12277
Reactions
Adenosine triphosphate + Creatine unknown ADP + Phosphocreatinedetails
Gene Name:
CKMT1A
Uniprot ID:
P12532
Reactions
Adenosine triphosphate + Creatine unknown ADP + Phosphocreatinedetails
Gene Name:
CKM
Uniprot ID:
P06732
Reactions
Adenosine triphosphate + Creatine unknown ADP + Phosphocreatinedetails
Gene Name:
PRRX1
Uniprot ID:
P54821

Transporters

Gene Name:
SLC22A5
Uniprot ID:
O76082