Human Metabolome Database Version 3.5

Showing metabocard for Creatine (HMDB00064)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:50 -0700
HMDB ID HMDB00064
Secondary Accession Numbers None
Metabolite Identification
Common Name Creatine
Description Creatine 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C4H9N3O2
Average Molecular Weight 131.1332
Monoisotopic Molecular Weight 131.069476547
IUPAC Name 2-(1-methylcarbamimidamido)acetic acid
Traditional IUPAC Name creatine
CAS Registry Number 57-00-1
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 Key CVSVTCORWBXHQV-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
  • amino acid zwitterion(ChEBI)
Substituents
  • Carboxylic Acid
  • Guanidine
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Arginine and proline metabolism
  • Component of Glycine, serine and threonine metabolism
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 303 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 13.3 mg/mL at 18 °C Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.11 g/L ALOGPS
LogP -1.59 ALOGPS
LogP -2.9 ChemAxon
LogS -1.50 ALOGPS
pKa (strongest acidic) 3.5 ChemAxon
pKa (strongest basic) 12.43 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 90.41 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 42.01 ChemAxon
Polarizability 12.2 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 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-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Neuron
  • Placenta
  • Testes
  • Kidney
  • Epidermis
  • Brain
  • Myelin
  • Prostate
  • Adipose Tissue
  • Nerve Cells
  • Platelet
  • Spleen
  • Heart
Pathways
Name SMPDB Link KEGG Link
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Arginine and Proline Metabolism SMP00020 map00330 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
54.8 +/- 21.0 uM Adult (>18 years old) Female Normal
Blood Detected and Quantified
30.1 +/- 12.3 uM Adult (>18 years old) Male Normal
Blood Detected and Quantified
84.0 +/- 23.2 uM Newborn (0-30 days old) Not Specified Normal
  • Geigy Scient...
Blood Detected and Quantified
53.0 (17.0 - 82.0) uM Children (1-13 year old) Not Specified Normal
  • Geigy Scient...
Blood Detected and Quantified
36.7 +/- 28.3 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
44 +/- 13 uM Not Specified Both Normal
Urine Detected and Quantified
113.0 (0.00-654.0) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
113(0-654) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.00-404.37 umol/mmol creatinine Adult (>18 years old) Both Normal
  • David F. Put...
Urine Detected and Quantified
46 (3-448) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
26.0 (5.0-95.0) umol/mmol creatinine Adult (>18 years old) Male Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
46.0 (9.0-135.0) umol/mmol creatinine Adult (>18 years old) Female Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
11.30 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Shaykhutdino...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 33.8 +/- 37.7 uM Adult (>18 years old) Not Specified Heart Transplant
Blood Detected and Quantified 40.3 (28.3-56.6) uM Adult (>18 years old) Female Cirrhosis
Blood Detected and Quantified 25.7 (16.5 - 30.8) uM Adult (>18 years old) Male Cirrhosis
Urine Detected and Quantified 37.0 (0.0-197.0) umol/mmol creatinine Not Specified Both Lung cancer
Urine Detected and Quantified 1540 umol/mmol creatinine Adult (>18 years old) Female Rhabdomyolysis
Associated Disorders and Diseases
Disease References
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 Link_out
      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 Link_out
          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 Link_out
              Associated OMIM IDs
              DrugBank ID DB00148 Link_out
              DrugBank Metabolite ID Not Available
              Phenol Explorer Compound ID Not Available
              Phenol Explorer Metabolite ID Not Available
              FoodDB ID FDB005403
              KNApSAcK ID Not Available
              Chemspider ID 566 Link_out
              KEGG Compound ID C00300 Link_out
              BioCyc ID CREATINE Link_out
              BiGG ID 34543 Link_out
              Wikipedia Link Creatine Link_out
              NuGOwiki Link HMDB00064 Link_out
              Metagene Link HMDB00064 Link_out
              METLIN ID 7 Link_out
              PubChem Compound 586 Link_out
              PDB ID CRN Link_out
              ChEBI ID 16919 Link_out
              References
              Synthesis Reference Thalhammer, 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. 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 Link_out
              2. 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 Link_out
              3. 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 Link_out
              4. 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 Link_out
              5. 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 Link_out
              6. 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 Link_out
              7. 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 Link_out
              8. 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 Link_out
              9. 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 Link_out
              10. 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 Link_out
              11. 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 Link_out
              12. 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 Link_out
              13. 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 Link_out
              14. 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 Link_out
              15. 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 Link_out
              16. 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 Link_out
              17. Yoshizumi WM, Tsourounis C: Effects of creatine supplementation on renal function. J Herb Pharmacother. 2004;4(1):1-7. Pubmed: 15273072 Link_out
              18. 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 Link_out
              19. 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 Link_out
              20. 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 Link_out
              21. 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 Link_out
              22. 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 Link_out
              23. 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 Link_out
              24. Juhn M: Popular sports supplements and ergogenic aids. Sports Med. 2003;33(12):921-39. Pubmed: 12974658 Link_out
              25. 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 Link_out

              Enzymes
              Name: Guanidinoacetate N-methyltransferase
              Reactions:
              S-Adenosylmethionine + Guanidoacetic acid unknown S-Adenosylhomocysteine + Creatine details
              Gene Name: GAMT
              Uniprot ID: Q14353 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Glycine amidinotransferase, mitochondrial
              Reactions: Not Available
              Gene Name: GATM
              Uniprot ID: P50440 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              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
              Name: Sodium- and chloride-dependent creatine transporter 1
              Reactions: Not Available
              Gene Name: SLC6A8
              Uniprot ID: P48029 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Paired mesoderm homeobox protein 1
              Reactions: Not Available
              Gene Name: PRRX1
              Uniprot ID: P54821 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: DNA-binding protein inhibitor ID-3
              Reactions: Not Available
              Gene Name: ID3
              Uniprot ID: Q02535 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Transporters
              Name: Solute carrier family 22 member 5
              Reactions: Not Available
              Gene Name: SLC22A5
              Uniprot ID: O76082 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA