NP-MRD: Showing NP-Card for Creatine (NP0001062)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-03 04:16:53 UTC

NP-MRD ID

NP0001062

Natural Product DOI

https://doi.org/10.57994/0846

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Creatine

Description

Creatine, is a naturally occurring non-protein compound. It 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. Creatine is found in all vertebrates where it facilitates recycling of adenosine triphosphate (ATP). Its primary metabolic role is to combine with a phosphoryl group, via the enzyme creatine kinase, to generate phosphocreatine, which is used to regenerate ATP. Most of the human body's total creatine and phosphocreatine stores are found in skeletal muscle (95%), while the remainder is distributed in the blood, brain, testes, and other tissues. Creatine is not an essential nutrient as it is naturally produced in the human body from the amino acids glycine and arginine, with an additional requirement for methionine to catalyze the transformation of guanidinoacetate to creatine. In the first step of its biosynthesis glycine and arginine are combined by the enzyme arginine:Glycine amidinotransferase (AGAT) to form guanidinoacetate, which is then methylated by guanidinoacetate N-methyltransferase (GAMT), using S-adenosyl methionine as the methyl donor. Creatine can also be obtained through the diet at a rate of about 1 gram per day from an omnivorous diet. A cyclic form of creatine, called creatinine, exists in equilibrium with its tautomer and with creatine. Clinically, there are three distinct disorders of creatine metabolism. Deficiencies in the two synthesis enzymes (AGAT and GAMT) can cause L-arginine:Glycine amidinotransferase deficiency (caused by variants in AGAT) and guanidinoacetate methyltransferase deficiency (caused by variants in GAMT). Both disorders are inherited in an autosomal recessive manner. A third defect, creatine transporter defect, is caused by mutations in SLC6A8 and inherited in a X-linked manner. Creatine is widely used as a supplement by athletes. Its use can increase maximum power and performance in high-intensity anaerobic repetitive work (periods of work and rest) by 5 to 15% (PMID: 24688272 ). Creatine has no significant effect on aerobic endurance, although it will increase power during short sessions of high-intensity aerobic exercise (PMID: 9662683 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol

Synonyms

Value	Source
((Amino(imino)methyl)(methyl)amino)acetic acid	ChEBI
(alpha-Methylguanido)acetic acid	ChEBI
(N-Methylcarbamimidamido)acetic acid	ChEBI
alpha-Methylguanidino acetic acid	ChEBI
Creatin	ChEBI
Kreatin	ChEBI
Methylglycocyamine	ChEBI
N-(Aminoiminomethyl)-N-methylglycine	ChEBI
N-[(e)-AMINO(imino)methyl]-N-methylglycine	ChEBI
N-Amidinosarcosine	ChEBI
N-Carbamimidoyl-N-methylglycine	ChEBI
N-Methyl-N-guanylglycine	ChEBI
((Amino(imino)methyl)(methyl)amino)acetate	Generator
(a-Methylguanido)acetate	Generator
(a-Methylguanido)acetic acid	Generator
(alpha-Methylguanido)acetate	Generator
(Α-methylguanido)acetate	Generator
(Α-methylguanido)acetic acid	Generator
(N-Methylcarbamimidamido)acetate	Generator
a-Methylguanidino acetate	Generator
a-Methylguanidino acetic acid	Generator
alpha-Methylguanidino acetate	Generator
Α-methylguanidino acetate	Generator
Α-methylguanidino acetic acid	Generator
Cosmocair C 100	HMDB
Creatine hydrate	HMDB
Krebiozon	HMDB
Methylguanidoacetate	HMDB
Methylguanidoacetic acid	HMDB
N-(Aminoiminomethyl)-N-methyl-glycine	HMDB
Phosphagen	HMDB
[[Amino(imino)methyl](methyl)amino]acetate	HMDB
[[Amino(imino)methyl](methyl)amino]acetic acid	HMDB

Chemical Formula

C₄H₉N₃O₂

Average Mass

131.1332 Da

Monoisotopic Mass

131.06948 Da

IUPAC Name

2-(N-methylcarbamimidamido)acetic acid

Traditional 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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, simulated)	Ahselim			2022-01-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	Not Available	Not Available	2023-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Capra aegagrus hircus	FooDB	FooDB
Carcharhinus obscurus	LOTUS Database	35616633
Carica papaya	KNApSAcK Database	22123792
Carica papaya L.	Plant	KNApSAcK
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Citrus natsudaidai	LOTUS Database	35616633
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Eriobotrya japonica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Lates calcarifer	LOTUS Database	35616633
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Litoria verreauxii	LOTUS Database	35616633
Lucilia sericata	LOTUS Database	35616633
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Thalassiosira pseudonana	LOTUS Database	35616633
Trypanosoma brucei	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Serum)	KNApSAcK Database	22123792
Homo sapiens (Urine)	KNApSAcK Database	22123792

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

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

glycine derivative (CHEBI:16919 )
guanidines (CHEBI:16919 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	303 °C	Not Available
Boiling Point	536.92 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	13.3 mg/mL at 18 °C	Not Available
LogP	10.982 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
Water Solubility	4.11 g/L	ALOGPS
logP	-1.6	ALOGPS
logP	-2.9	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.5	ChemAxon
pKa (Strongest Basic)	12.43	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.41 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.01 m³·mol⁻¹	ChemAxon
Polarizability	12.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000064

DrugBank ID

DB00148

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

586

PDB ID

Not Available

ChEBI ID

16919

Good Scents ID

rw1364761

References

General 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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:11522277 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Yoshizumi WM, Tsourounis C: Effects of creatine supplementation on renal function. J Herb Pharmacother. 2004;4(1):1-7. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:11600695 ]
Juhn M: Popular sports supplements and ergogenic aids. Sports Med. 2003;33(12):921-39. [PubMed:12974658 ]
Bird SP: Creatine supplementation and exercise performance: a brief review. J Sports Sci Med. 2003 Dec 1;2(4):123-32. eCollection 2003 Dec. [PubMed:24688272 ]
Engelhardt M, Neumann G, Berbalk A, Reuter I: Creatine supplementation in endurance sports. Med Sci Sports Exerc. 1998 Jul;30(7):1123-9. doi: 10.1097/00005768-199807000-00016. [PubMed:9662683 ]
Liu Y, Xia P, Cao W, Liu Z, Ma J, Zheng K, Chen L, Li X, Qin Y, Li X: Divergence between serum creatine and cystatin C in estimating glomerular filtration rate of critically ill COVID-19 patients. Ren Fail. 2021 Dec;43(1):1104-1114. doi: 10.1080/0886022X.2021.1948428. [PubMed:34238117 ]

Showing NP-Card for Creatine (NP0001062)

MOL for NP0001062 (Creatine)

3D MOL for NP0001062 (Creatine)

3D SDF for NP0001062 (Creatine)

3D-SDF for NP0001062 (Creatine)

PDB for NP0001062 (Creatine)

3D PDB for NP0001062 (Creatine)

SMILES for NP0001062 (Creatine)

INCHI for NP0001062 (Creatine)

Structure for NP0001062 (Creatine)

3D Structure for NP0001062 (Creatine)