Creatine

Synonyms :
((amino(Imino)methyl)(methyl)amino)acetic acid, (alpha-Methylguanido)acetic acid, (N-methylcarbamimidamido)acetic acid, (α-methylguanido)acetic acid, alpha-Methylguanidino acetic acid, Creatin, Creatine, Kreatin, Methylglycocyamine, N-(aminoiminomethyl)-N-methylglycine, N-[(e)-AMINO(imino)methyl]-N-methylglycine, N-Amidinosarcosine, N-Carbamimidoyl-N-methylglycine, N-Methyl-N-guanylglycine

Status : approved

Category

Dietary Supplements

Description

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. [PubChem]

Used

For nutritional supplementation, also for treating dietary shortage or imbalance

Mechanism Of Action

In the muscles, a fraction of the total creatine binds to phosphate – forming creatine phosphate. The reaction is catalysed by creatine kinase, and the result is phosphocreatine (PCr). Phosphocreatine binds with adenosine diphosphate to convert it back to ATP (adenosine triphosphate), an important cellular energy source for short term ATP needs prior to oxidative phosphorylation.

Pharmacodynamics

Creatine is a essential, non-proteinaceous amino acid found in all animals and, in some plants. Creatine is synthesized in the kidney, liver and pancreas from L-arginine, glycine and L-methionine. Following its biosynthesis, creatine is transported to the skeletal muscle, heart, brain and other tissues. Most of the creatine is metabolized in these tissues to phosphocreatine (creatine phosphate). Phosphocreatine is a major energy storage form in the body. Supplemental creatine may have an energy-generating action during anaerobic exercise and may also have neuroprotective and cardioprotective actions.

Half Life

3 hours

Chemical Classification

This compound belongs to the class of organic compounds 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.

Alpha amino acids and derivatives

Organic compounds

Organic acids and derivatives

Carboxylic acids and derivatives

Amino acids, peptides, and analogues

Chemical Name

((amino(Imino)methyl)(methyl)amino)acetic acid

Calculated Property

kind Value Source
logP -1.6 ALOGPS
logS -1.5 ALOGPS
Water Solubility 4.11e+00 g/l ALOGPS
logP -2.9 ChemAxon
IUPAC Name 2-(1-methylcarbamimidamido)acetic acid ChemAxon
Traditional IUPAC Name creatine ChemAxon
Molecular Weight 131.1332 ChemAxon
Monoisotopic Weight 131.069476547 ChemAxon
SMILES CN(CC(O)=O)C(N)=N ChemAxon
Molecular Formula C4H9N3O2 ChemAxon
InChI InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9) ChemAxon
InChIKey InChIKey=CVSVTCORWBXHQV-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 90.41 ChemAxon
Refractivity 42.01 ChemAxon
Polarizability 12.17 ChemAxon
Rotatable Bond Count 2 ChemAxon
H Bond Acceptor Count 5 ChemAxon
H Bond Donor Count 3 ChemAxon
pKa (strongest acidic) 3.5 ChemAxon
pKa (strongest basic) 12.43 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 0 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Creatine kinase M-type : in Human
  • Creatine kinase U-type, mitochondrial : in Human
  • Creatine kinase B-type : in Human
  • Creatine kinase S-type, mitochondrial : in Human
  • Sodium- and chloride-dependent creatine transporter 1 : in Human
  • Guanidinoacetate N-methyltransferase : in Human