Creatine
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Basic Info
| Common Name | Creatine(F05325) |
| 2D Structure | |
| 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. |
| FRCD ID | F05325 |
| CAS Number | 57-00-1 |
| PubChem CID | 586 |
| Formula | C4H9N3O2 |
| IUPAC Name | 2-[carbamimidoyl(methyl)amino]acetic acid |
| 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) |
| Canonical SMILES | CN(CC(=O)O)C(=N)N |
| Isomeric SMILES | CN(CC(=O)O)C(=N)N |
| Wikipedia | Creatine |
| Synonyms |
Kreatin
(alpha-Methylguanido)acetic acid
creatine
57-00-1
Creatin
Krebiozon
N-amidinosarcosine
N-methyl-N-guanylglycine
methylglycocyamine
Creatine, hydrate
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives |
| Direct Parent | Alpha amino acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| 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 |
| Description | 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 131.135 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 134 |
| Monoisotopic Mass | 131.069 |
| Exact Mass | 131.069 |
| XLogP | -1.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.6849 |
| Human Intestinal Absorption | HIA+ | 0.9605 |
| Caco-2 Permeability | Caco2- | 0.6228 |
| P-glycoprotein Substrate | Non-substrate | 0.5275 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9704 |
| Non-inhibitor | 0.8744 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8321 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5430 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7916 |
| CYP450 2D6 Substrate | Non-substrate | 0.7670 |
| CYP450 3A4 Substrate | Non-substrate | 0.7585 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9136 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9068 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8954 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9157 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9346 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9969 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9653 |
| Non-inhibitor | 0.9649 | |
| AMES Toxicity | Non AMES toxic | 0.7522 |
| Carcinogens | Non-carcinogens | 0.8138 |
| Fish Toxicity | Low FHMT | 0.9297 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.8568 |
| Honey Bee Toxicity | Low HBT | 0.7291 |
| Biodegradation | Not ready biodegradable | 0.7859 |
| Acute Oral Toxicity | III | 0.5560 |
| Carcinogenicity (Three-class) | Non-required | 0.5840 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.9464 | LogS |
| Caco-2 Permeability | 0.2911 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0088 | LD50, mol/kg |
| Fish Toxicity | 2.6160 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.5670 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Toxicological analysis of roast duck flavor components. | Food Chem Toxicol | 2018 Sep | 29208505 |
| Metabonomics profiling of marinated meat in soy sauce during processing. | J Sci Food Agric | 2018 Mar | 28758223 |
| Postpartum ketoprofen treatment does not alter stress biomarkers in cows andcalves experiencing assisted and unassisted parturition: a randomised controlled trial. | Vet Rec | 2018 Jun 30 | 29960984 |
| 1H-nuclear magnetic resonance metabolomics revealing the intrinsic relationships between neurochemical alterations and neurobehavioral and neuropathologicalabnormalities in rats exposed to tris(2-chloroethyl)phosphate. | Chemosphere | 2018 Jun | 29518649 |
| Toxicological effects of Nux Vomica in rats urine and serum by means of clinical chemistry, histopathology and <sup>1</sup>H NMR-based metabonomics approach. | J Ethnopharmacol | 2018 Jan 10 | 28648929 |
| Performance and serum biochemical profile of Japanese quail supplemented with silymarin and contaminated with aflatoxin B1. | Poult Sci | 2018 Jan 1 | 29077959 |
| Beneficial effects of fermented camel milk by lactococcus lactis subsp cremoris on cardiotoxicity induced by carbon tetrachloride in mice. | Biomed Pharmacother | 2018 Jan | 29080450 |
| Metabolomic analysis of CSF indicates brain metabolic impairment precedeshematological indices of anemia in the iron-deficient infant monkey. | Nutr Neurosci | 2018 Jan | 27499134 |
| Real-Time Monitoring of Chemical Changes in Three Kinds of Fermented MilkProducts during Fermentation Using Quantitative Difference Nuclear MagneticResonance Spectroscopy. | J Agric Food Chem | 2018 Feb 14 | 29342350 |
| Investigation of the Protective Effect of Kefir against Isoproterenol Induced Myocardial Infarction in Rats. | Korean J Food Sci Anim Resour | 2018 Apr | 29805276 |
| The microbiome of professional athletes differs from that of more sedentarysubjects in composition and particularly at the functional metabolic level. | Gut | 2018 Apr | 28360096 |
| In ovo feeding of creatine pyruvate alters energy reserves, satellite cellmitotic activity and myogenic gene expression of breast muscle in embryos andneonatal broilers. | Poult Sci | 2017 Sep 1 | 28854747 |
| Kidney toxicity related to herbs and dietary supplements: Online table of case reports. Part 3 of 5 series. | Food Chem Toxicol | 2017 Sep | 28755953 |
| Mate extract as feed additive for improvement of beef quality. | Food Res Int | 2017 Sep | 28784491 |
| Survival After Severe Rhabdomyolysis Following Monensin Ingestion. | J Med Toxicol | 2017 Sep | 28516409 |
| Aspartame and Soft Drink-Mediated Neurotoxicity in Rats: Implication of OxidativeStress, Apoptotic Signaling Pathways, Electrolytes and Hormonal Levels. | Metab Brain Dis | 2017 Oct | 28660358 |
| Effect of feeding Rumen-protected capsule containing niacin, K2SO4, vitamin C,and gamma-aminobutyric acid on heat stress and performance of dairy cows. | J Therm Biol | 2017 Oct | 29037390 |
| The hematological and biochemical changes in rats exposed to britholite mineral. | Appl Radiat Isot | 2017 Nov | 28869870 |
| Equine atypical myopathy in the UK: Epidemiological characteristics of cases reported from 2011 to 2015 and factors associated with survival. | Equine Vet J | 2017 Nov | 28445006 |
| NMR Metabolomics Investigates the Influence of Flavonoid-Enriched Rations onChicken Plasma. | J AOAC Int | 2017 Mar 1 | 28063211 |
Targets
- General Function:
- Creatine kinase activity
- Specific Function:
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
- Gene Name:
- CKMT2
- Uniprot ID:
- P17540
- Molecular Weight:
- 47504.08 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Creatine kinase activity
- Specific Function:
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
- Gene Name:
- CKMT1A
- Uniprot ID:
- P12532
- Molecular Weight:
- 47036.3 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Neurotransmitter:sodium symporter activity
- Specific Function:
- Required for the uptake of creatine in muscles and brain.
- Gene Name:
- SLC6A8
- Uniprot ID:
- P48029
- Molecular Weight:
- 70522.17 Da
References
- Rosenberg EH, Munoz CM, Degrauw TJ, Jakobs Cn, Salomons GS: Overexpression of wild-type creatine transporter (SLC6A8) restores creatine uptake in primary SLC6A8-deficient fibroblasts. J Inherit Metab Dis. 2006 Apr-Jun;29(2-3):345-6. [16763899 ]
- General Function:
- Ubiquitin protein ligase binding
- Specific Function:
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
- Gene Name:
- CKB
- Uniprot ID:
- P12277
- Molecular Weight:
- 42643.95 Da
References
- Wallimann T, Wyss M, Brdiczka D, Nicolay K, Eppenberger HM: Intracellular compartmentation, structure and function of creatine kinase isoenzymes in tissues with high and fluctuating energy demands: the 'phosphocreatine circuit' for cellular energy homeostasis. Biochem J. 1992 Jan 1;281 ( Pt 1):21-40. [1731757 ]
- General Function:
- Creatine kinase activity
- Specific Function:
- Reversibly catalyzes the transfer of phosphate between ATP and various phosphogens (e.g. creatine phosphate). Creatine kinase isoenzymes play a central role in energy transduction in tissues with large, fluctuating energy demands, such as skeletal muscle, heart, brain and spermatozoa.
- Gene Name:
- CKM
- Uniprot ID:
- P06732
- Molecular Weight:
- 43100.91 Da
References
- Zeng L, Hu Q, Wang X, Mansoor A, Lee J, Feygin J, Zhang G, Suntharalingam P, Boozer S, Mhashilkar A, Panetta CJ, Swingen C, Deans R, From AH, Bache RJ, Verfaillie CM, Zhang J: Bioenergetic and functional consequences of bone marrow-derived multipotent progenitor cell transplantation in hearts with postinfarction left ventricular remodeling. Circulation. 2007 Apr 10;115(14):1866-75. Epub 2007 Mar 26. [17389266 ]
- General Function:
- Methyltransferase activity
- Gene Name:
- GAMT
- Uniprot ID:
- Q14353
- Molecular Weight:
- 26317.925 Da
References
- Wang L, Zhang Y, Shao M, Zhang H: Spatiotemporal expression of the creatine metabolism related genes agat, gamt and ct1 during zebrafish embryogenesis. Int J Dev Biol. 2007;51(3):247-53. [17486546 ]
- General Function:
- L-proline transmembrane transporter activity
- Specific Function:
- Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recognize their D-enantiomers and selected amino acid derivatives such as gamma-aminobutyric acid (By similarity).
- Gene Name:
- SLC36A1
- Uniprot ID:
- Q7Z2H8
- Molecular Weight:
- 53075.045 Da
References
- Thondorf I, Voigt V, Schafer S, Gebauer S, Zebisch K, Laug L, Brandsch M: Three-dimensional quantitative structure-activity relationship analyses of substrates of the human proton-coupled amino acid transporter 1 (hPAT1). Bioorg Med Chem. 2011 Nov 1;19(21):6409-18. doi: 10.1016/j.bmc.2011.08.058. Epub 2011 Sep 5. [21955456 ]