Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110649
Identification
Name: creatine
Description:Zwitterionic form of creatine arising from transfer of a proton from the carboxy to the guanidino group; major species at pH 7.3.
Structure
Thumb
Synonyms:
  • methylguanidinoacetic acid
  • N-amidinosarcosine
  • methylglycocyamine
  • N-methyl-N-guanylglycine
Chemical Formula: C4H9N3O2
Average Molecular Weight: 131.13
Monoisotopic Molecular Weight: 132.0773015808
InChI Key: CVSVTCORWBXHQV-UHFFFAOYSA-N
InChI: InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)
CAS number: 57-00-1
IUPAC Name:{[amino(iminio)methyl](methyl)amino}acetate
Traditional IUPAC Name: creatine
SMILES:C(C(=O)[O-])N(C)C(N)=[N+]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Alpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Guanidine
  • Carboximidamide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 303 °C
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 mg/mLALOGPS
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 Area90.41 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.01 m3·mol-1ChemAxon
Polarizability12.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000x-9800000000-bc1387ab36f71e04b988View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-6c686da36a88d9fbdbcfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-13b7d28e8f5be1c5dadaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-cc4bd4c587dd80f63bcbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-3900000000-d35c7578ad50de8377b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-a4d7fee14f74e1ed8b4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-e5d62520dfcbf4bfe5c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-06fbcf897ccce3fa90b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-9a0b8275e74605a92681View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000f-9000000000-5f622f2c3de4f213a8edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-20ba65c7a2c9434fcf39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-01qc-0965022201-53bb6f168e0934ae4a87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-9000000000-638479794e8c3a6e0b61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0900000000-39676937b1a3ad0dc0bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0090000000-d53c75786742ecdb3c16View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001l-0945022201-2fc3f234454021c5e202View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-9000000000-40aa07f89dddb181e489View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0900000000-5aca4d0b8ed7d2500af2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0190000000-9a9685c32bf6c721a497View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-1900000000-c99f9492e0b84d5fae6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9300000000-8ab609e6dd62bd18841fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-e04e407d5f06d21582c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-fd81d06317727fa740b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-8428e2af90720afb4337View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-0900000000-3162b4c94e66796a643bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-47f885347545055f546dView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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. [15627241 ]
  • 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. [6321058 ]
  • 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. [12851769 ]
  • 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. [16855203 ]
  • 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. [16331129 ]
  • 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. [16416332 ]
  • 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. [11570870 ]
  • 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. [16581862 ]
  • 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. [10825659 ]
  • 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. [11375287 ]
  • 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. [11522277 ]
  • 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. [6411064 ]
  • 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. [16509464 ]
  • 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. [9475367 ]
  • 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. [16287366 ]
  • 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. [15902992 ]
  • 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. [16260971 ]
  • Yoshizumi WM, Tsourounis C: Effects of creatine supplementation on renal function. J Herb Pharmacother. 2004;4(1):1-7. [15273072 ]
  • 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. [15513279 ]
  • 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. [15302082 ]
  • 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. [14669930 ]
  • 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. [8828669 ]
  • 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. [10683092 ]
  • 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. [11600695 ]
  • Juhn M: Popular sports supplements and ergogenic aids. Sports Med. 2003;33(12):921-39. [12974658 ]
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)
External Links:
ResourceLink
CAS57-00-1
ChEBI57947
ChemSpider5414502
HMDBHMDB00064
KEGGC00300
MetaboLightsMTBLC57947
PubChem7058172