CHEBI:16919 - creatine

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ChEBI Name creatine
ChEBI ID CHEBI:16919
Definition A glycine derivative having methyl and amidino groups attached to the nitrogen.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:23404, CHEBI:41678, CHEBI:3909, CHEBI:14028
Supplier Information ChemicalBook:CB3674978, eMolecules:494174, ZINC000003861770
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Creatine ( or ) is an organic compound with the nominal formula (H2N)(HN)CN(CH3)CH2CO2H. It exists in various tautomers in solutions (among which are neutral form and various zwitterionic forms). Creatine is found in vertebrates, where it facilitates recycling of adenosine triphosphate (ATP), primarily in muscle and brain tissue. Recycling is achieved by converting adenosine diphosphate (ADP) back to ATP via donation of phosphate groups. Creatine also acts as a buffer.
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Formula C4H9N3O2
Net Charge 0
Average Mass 131.13328
Monoisotopic Mass 131.06948
InChI InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)
InChIKey CVSVTCORWBXHQV-UHFFFAOYSA-N
SMILES CN(CC(O)=O)C(N)=N
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Homo sapiens (NCBI:txid9606) See: PubMed
Homo sapiens (NCBI:txid9606) Found in blood serum (BTO:0000133). See: MetaboLights Study
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
neuroprotective agent
Any compound that can be used for the treatment of neurodegenerative disorders.
nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing creatine (CHEBI:16919) has role geroprotector (CHEBI:176497)
creatine (CHEBI:16919) has role human metabolite (CHEBI:77746)
creatine (CHEBI:16919) has role mouse metabolite (CHEBI:75771)
creatine (CHEBI:16919) has role neuroprotective agent (CHEBI:63726)
creatine (CHEBI:16919) has role nutraceutical (CHEBI:50733)
creatine (CHEBI:16919) is a glycine derivative (CHEBI:24373)
creatine (CHEBI:16919) is a guanidines (CHEBI:24436)
creatine (CHEBI:16919) is conjugate acid of creatinate (CHEBI:66924)
creatine (CHEBI:16919) is tautomer of creatine zwitterion (CHEBI:57947)
Incoming N-phosphocreatine (CHEBI:17287) has functional parent creatine (CHEBI:16919)
creatinine (CHEBI:16737) has functional parent creatine (CHEBI:16919)
creatinate (CHEBI:66924) is conjugate base of creatine (CHEBI:16919)
creatine zwitterion (CHEBI:57947) is tautomer of creatine (CHEBI:16919)
IUPAC Name
N-[amino(imino)methyl]-N-methylglycine
Synonyms Sources
((amino(imino)methyl)(methyl)amino)acetic acid HMDB
(α-methylguanido)acetic acid HMDB
(α-methylguanido)acetic acid NIST Chemistry WebBook
(N-methylcarbamimidamido)acetic acid ChEBI
alpha-Methylguanidino acetic acid KEGG COMPOUND
Creatin ChemIDplus
Creatine KEGG COMPOUND
Kreatin ChemIDplus
Methylglycocyamine KEGG COMPOUND
N-(aminoiminomethyl)-N-methylglycine NIST Chemistry WebBook
N-[(E)-AMINO(IMINO)METHYL]-N-METHYLGLYCINE PDBeChem
N-amidinosarcosine ChemIDplus
N-carbamimidoyl-N-methylglycine PDBeChem
N-Methyl-N-guanylglycine HMDB
N-methyl-N-guanylglycine ChemIDplus
Manual Xrefs Databases
4661 DrugCentral
566 ChemSpider
C00300 KEGG COMPOUND
Creatine Wikipedia
CREATINE MetaCyc
CRN PDBeChem
DB00148 DrugBank
HMDB0000064 HMDB
View more database links
Registry Numbers Types Sources
240513 Gmelin Registry Number Gmelin
57-00-1 CAS Registry Number KEGG COMPOUND
57-00-1 CAS Registry Number ChemIDplus
57-00-1 CAS Registry Number NIST Chemistry WebBook
907175 Reaxys Registry Number Reaxys
Citations
Dulinska J, Setkowicz Z, Janeczko K, Sandt C, Dumas P, Uram L, Gzielo-Jurek K, Chwiej J (2012)
Synchrotron radiation Fourier-transform infrared and Raman microspectroscopy study showing an increased frequency of creatine inclusions in the rat hippocampal formation following pilocarpine-induced seizures.
Analytical and bioanalytical chemistry 402, 2267-2274 [PubMed:22038587]
[show Abstract]
Orsenigo MN, Porta C, Sironi C, Laforenza U, Meyer G, Tosco M (2012)
Effects of creatine in a rat intestinal model of ischemia/reperfusion injury.
European journal of nutrition 51, 375-384 [PubMed:21698493]
[show Abstract]
Stimpson SA, Turner SM, Clifton LG, Poole JC, Mohammed HA, Shearer TW, Waitt GM, Hagerty LL, Remlinger KS, Hellerstein MK, Evans WJ (2012)
Total-body creatine pool size and skeletal muscle mass determination by creatine-(methyl-D3) dilution in rats.
Journal of applied physiology (Bethesda, Md. : 1985) 112, 1940-1948 [PubMed:22422801]
[show Abstract]
Braissant O (2012)
Creatine and guanidinoacetate transport at blood-brain and blood-cerebrospinal fluid barriers.
Journal of inherited metabolic disease 35, 655-664 [PubMed:22252611]
[show Abstract]
Valayannopoulos V, Boddaert N, Chabli A, Barbier V, Desguerre I, Philippe A, Afenjar A, Mazzuca M, Cheillan D, Munnich A, de Keyzer Y, Jakobs C, Salomons GS, de Lonlay P (2012)
Treatment by oral creatine, L-arginine and L-glycine in six severely affected patients with creatine transporter defect.
Journal of inherited metabolic disease 35, 151-157 [PubMed:21660517]
[show Abstract]
van de Kamp JM, Pouwels PJ, Aarsen FK, ten Hoopen LW, Knol DL, de Klerk JB, de Coo IF, Huijmans JG, Jakobs C, van der Knaap MS, Salomons GS, Mancini GM (2012)
Long-term follow-up and treatment in nine boys with X-linked creatine transporter defect.
Journal of inherited metabolic disease 35, 141-149 [PubMed:21556832]
[show Abstract]
Berti SL, Nasi GM, Garcia C, Castro FL, Nunes ML, Rojas DB, Moraes TB, Dutra-Filho CS, Wannmacher CM (2012)
Pyruvate and creatine prevent oxidative stress and behavioral alterations caused by phenylalanine administration into hippocampus of rats.
Metabolic brain disease 27, 79-89 [PubMed:22101931]
[show Abstract]
Ndika JD, Johnston K, Barkovich JA, Wirt MD, O'Neill P, Betsalel OT, Jakobs C, Salomons GS (2012)
Developmental progress and creatine restoration upon long-term creatine supplementation of a patient with arginine:glycine amidinotransferase deficiency.
Molecular genetics and metabolism 106, 48-54 [PubMed:22386973]
[show Abstract]
Shen H, Goldberg MP (2012)
Creatine pretreatment protects cortical axons from energy depletion in vitro.
Neurobiology of disease 47, 184-193 [PubMed:22521466]
[show Abstract]
Allen PJ (2012)
Creatine metabolism and psychiatric disorders: Does creatine supplementation have therapeutic value?
Neuroscience and biobehavioral reviews 36, 1442-1462 [PubMed:22465051]
[show Abstract]
Garcia P, Rodrigues F, Valongo C, Salomons GS, Diogo L (2012)
Phenotypic variability in a portuguese family with x-linked creatine transport deficiency.
Pediatric neurology 46, 39-41 [PubMed:22196490]
[show Abstract]
Allen PJ, D'Anci KE, Kanarek RB, Renshaw PF (2012)
Sex-specific antidepressant effects of dietary creatine with and without sub-acute fluoxetine in rats.
Pharmacology, biochemistry, and behavior 101, 588-601 [PubMed:22429992]
[show Abstract]
Genius J, Geiger J, Bender A, Möller HJ, Klopstock T, Rujescu D (2012)
Creatine protects against excitoxicity in an in vitro model of neurodegeneration.
PloS one 7, e30554 [PubMed:22347384]
[show Abstract]
Shariff MI, Ladep NG, Cox IJ, Williams HR, Okeke E, Malu A, Thillainayagam AV, Crossey MM, Khan SA, Thomas HC, Taylor-Robinson SD (2010)
Characterization of urinary biomarkers of hepatocellular carcinoma using magnetic resonance spectroscopy in a Nigerian population.
Journal of proteome research 9, 1096-1103 [PubMed:19968328]
[show Abstract]
Sakkas GK, Schambelan M, Mulligan K (2009)
Can the use of creatine supplementation attenuate muscle loss in cachexia and wasting?
Current opinion in clinical nutrition and metabolic care 12, 623-627 [PubMed:19741514]
[show Abstract]
Jahangir E, Vita JA, Handy D, Holbrook M, Palmisano J, Beal R, Loscalzo J, Eberhardt RT (2009)
The effect of L-arginine and creatine on vascular function and homocysteine metabolism.
Vascular medicine (London, England) 14, 239-248 [PubMed:19651674]
[show Abstract]
Sartorius A, Lugenbiel P, Mahlstedt MM, Ende G, Schloss P, Vollmayr B (2008)
Proton magnetic resonance spectroscopic creatine correlates with creatine transporter protein density in rat brain.
Journal of neuroscience methods 172, 215-219 [PubMed:18555535]
[show Abstract]
Gipson GT, Tatsuoka KS, Ball RJ, Sokhansanj BA, Hansen MK, Ryan TE, Hodson MP, Sweatman BC, Connor SC (2008)
Multi-platform investigation of the metabolome in a leptin receptor defective murine model of type 2 diabetes.
Molecular bioSystems 4, 1015-1023 [PubMed:19082141]
[show Abstract]
Bender A, Beckers J, Schneider I, Hölter SM, Haack T, Ruthsatz T, Vogt-Weisenhorn DM, Becker L, Genius J, Rujescu D, Irmler M, Mijalski T, Mader M, Quintanilla-Martinez L, Fuchs H, Gailus-Durner V, de Angelis MH, Wurst W, Schmidt J, Klopstock T (2008)
Creatine improves health and survival of mice.
Neurobiology of aging 29, 1404-1411 [PubMed:17416441]
[show Abstract]
Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL (2007)
A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human.
Physiological genomics 29, 99-108 [PubMed:17190852]
[show Abstract]
Kley RA, Vorgerd M, Tarnopolsky MA (2007)
Creatine for treating muscle disorders.
The Cochrane database of systematic reviewsCD004760 [PubMed:17253521]
[show Abstract]
Burguera EF, Love BJ (2006)
Reduced transglutaminase-catalyzed protein aggregation is observed in the presence of creatine using sedimentation velocity.
Analytical biochemistry 350, 113-119 [PubMed:16445883]
[show Abstract]
Gao F, Bottomley PA, Arnold C, Weiss RG (2003)
The effect of orientation on quantification of muscle creatine by 1H MR spectroscopy.
Magnetic resonance imaging 21, 561-566 [PubMed:12878267]
[show Abstract]
Mendes RR, Tirapegui J (2002)
[Creatine: the nutritional supplement for exercise - current concepts].
Archivos latinoamericanos de nutricion 52, 117-127 [PubMed:12184144]
[show Abstract]
Davydov VV, Shvets VN, Shvets VN (2002)
Adenine nucleotide and creatine phosphate pool in adult and old rat heart during immobilization stress.
Gerontology 48, 81-83 [PubMed:11867929]
[show Abstract]
McGuine TA, Sullivan JC, Bernhardt DA (2002)
Creatine supplementation in Wisconsin high school athletes.
WMJ : official publication of the State Medical Society of Wisconsin 101, 25-30 [PubMed:12085493]
[show Abstract]
Metzl JD, Small E, Levine SR, Gershel JC (2001)
Creatine use among young athletes.
Pediatrics 108, 421-425 [PubMed:11483809]
[show Abstract]
Persky AM, Brazeau GA (2001)
Clinical pharmacology of the dietary supplement creatine monohydrate.
Pharmacological reviews 53, 161-176 [PubMed:11356982]
[show Abstract]
Marescau B, De Deyn PP, Holvoet J, Possemiers I, Nagels G, Saxena V, Mahler C (1995)
Guanidino compounds in serum and urine of cirrhotic patients.
Metabolism: clinical and experimental 44, 584-588 [PubMed:7752905]
[show Abstract]
Last Modified
20 September 2021