Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

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 | 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 Comments
Blood Detected and Quantified
Article_icon
54.8 +/- 21.0 uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
Article_icon
30.1 +/- 12.3 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
Article_icon
84.0 +/- 23.2 uM Newborn (0-30 days old) Not Specified Normal Not Available
Blood Detected and Quantified
Article_icon
53.0 (17.0 - 82.0) uM Children (1-13 year old) Not Specified Normal Not Available
Blood Detected and Quantified
Article_icon
36.7 +/- 28.3 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
44 +/- 13 uM Not Specified Both Normal Not Available
Urine Detected and Quantified
Article_icon
113.0 (0.00-654.0) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
113(0-654) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
0.00-404.37 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
Article_icon
46 (3-448) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
Article_icon
26.0 (5.0-95.0) umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
Article_icon
46.0 (9.0-135.0) umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
Article_icon
11.30 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
33.8 +/- 37.7 uM Adult (>18 years old) Not Specified Heart Transplant Not Available
Blood Detected and Quantified
Article_icon
40.3 (28.3-56.6) uM Adult (>18 years old) Female Cirrhosis Not Available
Blood Detected and Quantified
Article_icon
25.7 (16.5 - 30.8) uM Adult (>18 years old) Male Cirrhosis Not Available
Urine Detected and Quantified
Article_icon
37.0 (0.0-197.0) umol/mmol creatinine Not Specified Both Lung cancer Not Available
Urine Detected and Quantified
Article_icon
1540 umol/mmol creatinine Adult (>18 years old) Female Rhabdomyolysis Not Available
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
        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
        Enzymes
        Name: Guanidinoacetate N-methyltransferase
        Reactions:
        • S-adenosyl-L-methionine + guanidinoacetate = S-adenosyl-L-homocysteine + creatine [RN:R01883]
        Gene Name: GAMT
        Uniprot ID: Q14353 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Glycine amidinotransferase, mitochondrial
        Reactions:
        • L-arginine + glycine = L-ornithine + guanidinoacetate [RN:R00565]
        Gene Name: GATM
        Uniprot ID: P50440 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Creatine kinase S-type, mitochondrial
        Reactions:
        • ATP + creatine = ADP + phosphocreatine [RN:R01881]
        Gene Name: CKMT2
        Uniprot ID: P17540 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Creatine kinase B-type
        Reactions:
        • ATP + creatine = ADP + phosphocreatine [RN:R01881]
        Gene Name: CKB
        Uniprot ID: P12277 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Creatine kinase U-type, mitochondrial
        Reactions:
        • ATP + creatine = ADP + phosphocreatine [RN:R01881]
        Gene Name: CKMT1A
        Uniprot ID: P12532 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Creatine kinase M-type
        Reactions:
        • ATP + creatine = ADP + phosphocreatine [RN:R01881]
        Gene Name: CKM
        Uniprot ID: P06732 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Sodium- and chloride-dependent creatine transporter 1
        Reactions:
        • --- []
        Gene Name: SLC6A8
        Uniprot ID: P48029 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Paired mesoderm homeobox protein 1
        Reactions:
          Gene Name: PRRX1
          Uniprot ID: P54821 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: DNA-binding protein inhibitor ID-3
          Reactions:
            Gene Name: ID3
            Uniprot ID: Q02535 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Transporters
            Name: Solute carrier family 22 member 5
            Reactions:
            • --- []
            Gene Name: SLC22A5
            Uniprot ID: O76082 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA