NP-MRD: Showing NP-Card for Phosphocreatine (NP0000169)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-06-29 00:47:05 UTC

NP-MRD ID

NP0000169

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phosphocreatine

Description

Phosphocreatine, also known as creatine phosphate (CP) or PCr (Pcr), is a phosphorylated creatine molecule that serves as a rapidly mobilizable reserve of high-energy phosphates in skeletal muscle, myocardium and the brain to recycle adenosine triphosphate, the energy currency of the cell. Phosphocreatine undergoes irreversible cyclization and dehydration to form creatinine at a fractional rate of 0.026 Per day, thus forming approximately 2 g creatinine/day in an adult male. This is the amount of creatine that must be provided either from dietary sources or by endogenous synthesis to maintain the body pool of (creatine and) phosphocreatine. Creatine is an amino acid that plays a vital role as phosphocreatine in regenerating adenosine triphosphate in skeletal muscle to energize muscle contraction. Creatine is phosphorylated to phosphocreatine in muscle in a reaction that is catalyzed by the enzyme creatine kinase. This enzyme is in highest concentration in muscle and nerve. Oral administration increases muscle stores. During the past decade, creatine has assumed prominence as an ergogenic (and legal) aid for professional and elite athletes. Most (~ 95%) of the total body creatine-phosphocreatine pool is in muscle (more in skeletal muscle than in smooth muscle) and amounts to 120 g (or 925 mmol) in a 70 kg adult male. Approximately 60-67% of the content in resting muscle is in the phosphorylated form. This generates enough ATP at the myofibrillar apparatus to power about 4 seconds of muscle contraction in exercise. Phosphocreatine reacts with ADP to yield ATP and creatine; the reversible reaction is catalyzed by creatine kinase. Phosphocreatine is the chief store of high-energy phosphates in muscle. Thus, this reaction, which permits the rephosphorylation of ADP to ATP, is the immediate source of energy in muscle contraction. During rest, metabolic processes regenerate phosphocreatine stores. In normal muscle, ATP that is broken down to ADP is immediately rephosphorylated to ATP. Thus, phosphocreatine serves as a reservoir of ATP-synthesizing potential. Phosphocreatine is the only fuel available to precipitously regenerate ATP during episodes of rapid fluctuations in demand. The availability of phosphocreatine likely limits muscle performance during brief, high-power exercise, i.E., Maximal exercise of short duration. With near maximal isometric contraction, the rate of utilization of phosphocreatine declines after 1-2 seconds of contraction, prior to the glycolysis peak at approximately 3 seconds (PMID: 10079702 ).

Structure

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

HEADER    PROTEIN                                 25-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAR-20         0                                  
HETATM    1  C   UNK     0    8693.1548694.261   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8694.4918693.492   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0    8691.8218693.492   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0    8693.1548695.801   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0    8695.8278694.261   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8694.4918691.952   0.000  0.00  0.00           C+0
HETATM    7  P   UNK     0    8690.4878694.261   0.000  0.00  0.00           P+0
HETATM    8  C   UNK     0    8697.1598693.492   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8691.2598695.597   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8689.1498693.488   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8689.7198695.597   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8698.4918694.261   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8697.1598691.952   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    2    8                                                       
CONECT    6    2                                                            
CONECT    7    3    9   10   11                                             
CONECT    8    5   12   13                                                  
CONECT    9    7                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
Creatine phosphate	ChEBI
Creatine phosphic acid	ChEBI
N-(N-Phosphonoamido)sarcosine	ChEBI
N-(Phosphonoamidino)sarcosine	ChEBI
N-Phosphorylcreatine	ChEBI
N(Omega)-phosphonocreatine	ChEBI
Phosphorylcreatine	ChEBI
{[imino(phosphonoamino)methyl](methyl)amino}acetic acid	ChEBI
N-Phosphocreatine	Kegg
Creatine phosphoric acid	Generator
{[imino(phosphonoamino)methyl](methyl)amino}acetate	Generator
Creatine-p	HMDB
Creatine-phosphate	HMDB
Creatinephosphoric acid	HMDB
N-(Phosphonoamidino)-sarcosine	HMDB
N-Phosphorocreatine	HMDB
N-[Imino(phosphonoamino)methyl]-N-methyl-glycine	HMDB
Neo-ton	HMDB
p-Creatine	HMDB

Chemical Formula

C₄H₁₀N₃O₅P

Average Mass

211.1131 Da

Monoisotopic Mass

211.03581 Da

IUPAC Name

2-(N-methyl-N'-phosphonocarbamimidamido)acetic acid

Traditional Name

creatine-phosphate

CAS Registry Number

67-07-2

SMILES

CN(CC(O)=O)C(=N)NP(O)(O)=O

InChI Identifier

InChI=1S/C4H10N3O5P/c1-7(2-3(8)9)4(5)6-13(10,11)12/h2H2,1H3,(H,8,9)(H4,5,6,10,11,12)

InChI Key

DRBBFCLWYRJSJZ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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
Apis cerana	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Lates calcarifer	LOTUS Database	35616633
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
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

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
Organic phosphoric acid derivative
Guanidine
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

phosphagen (CHEBI:17287 )
phosphoamino acid (CHEBI:17287 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.52 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	-1.1	ChemAxon
pKa (Strongest Basic)	13.53	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	133.95 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.18 m³·mol⁻¹	ChemAxon
Polarizability	16.82 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

HMDB0001511

DrugBank ID

DB13191

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022665

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17287

Good Scents ID

Not Available

References

General References

Pastoris O, Dossena M, Foppa P, Catapano M, Arbustini E, Bellini O, Dal Bello B, Minzioni G, Ceriana P, Barzaghi N: Effect of L-carnitine on myocardial metabolism: results of a balanced, placebo-controlled, double-blind study in patients undergoing open heart surgery. Pharmacol Res. 1998 Feb;37(2):115-22. [PubMed:9572066 ]
Schmidt A, Marescau B, Boehm EA, Renema WK, Peco R, Das A, Steinfeld R, Chan S, Wallis J, Davidoff M, Ullrich K, Waldschutz R, Heerschap A, De Deyn PP, Neubauer S, Isbrandt D: Severely altered guanidino compound levels, disturbed body weight homeostasis and impaired fertility in a mouse model of guanidinoacetate N-methyltransferase (GAMT) deficiency. Hum Mol Genet. 2004 May 1;13(9):905-21. Epub 2004 Mar 17. [PubMed:15028668 ]
Gideon P, Henriksen O, Sperling B, Christiansen P, Olsen TS, Jorgensen HS, Arlien-Soborg P: Early time course of N-acetylaspartate, creatine and phosphocreatine, and compounds containing choline in the brain after acute stroke. A proton magnetic resonance spectroscopy study. Stroke. 1992 Nov;23(11):1566-72. [PubMed:1440704 ]
Green AL, Hultman E, Macdonald IA, Sewell DA, Greenhaff PL: Carbohydrate ingestion augments skeletal muscle creatine accumulation during creatine supplementation in humans. Am J Physiol. 1996 Nov;271(5 Pt 1):E821-6. [PubMed:8944667 ]
Skare OC, Skadberg, Wisnes AR: Creatine supplementation improves sprint performance in male sprinters. Scand J Med Sci Sports. 2001 Apr;11(2):96-102. [PubMed:11252467 ]
Greenhaff PL, Soderlund K, Ren JM, Hultman E: Energy metabolism in single human muscle fibres during intermittent contraction with occluded circulation. J Physiol. 1993 Jan;460:443-53. [PubMed:8487203 ]
Greiner A, Esterhammer R, Pilav S, Arnold W, Santner W, Neuhauser B, Fraedrich G, Jaschke WR, Schocke MF: High-energy phosphate metabolism in the calf muscle during moderate isotonic exercise under different degrees of cuff compression: a phosphorus 31 magnetic resonance spectroscopy study. J Vasc Surg. 2005 Aug;42(2):259-67. [PubMed:16102624 ]
Murphy AJ, Watsford ML, Coutts AJ, Richards DA: Effects of creatine supplementation on aerobic power and cardiovascular structure and function. J Sci Med Sport. 2005 Sep;8(3):305-13. [PubMed:16248471 ]
Braegger CP, Schlattner U, Wallimann T, Utiger A, Frank F, Schaefer B, Heizmann CW, Sennhauser FH: Effects of creatine supplementation in cystic fibrosis: results of a pilot study. J Cyst Fibros. 2003 Dec;2(4):177-82. [PubMed:15463870 ]
Kemp GJ, Hands LJ, Ramaswami G, Taylor DJ, Nicolaides A, Amato A, Radda GK: Calf muscle mitochondrial and glycogenolytic ATP synthesis in patients with claudication due to peripheral vascular disease analysed using 31P magnetic resonance spectroscopy. Clin Sci (Lond). 1995 Dec;89(6):581-90. [PubMed:8549076 ]
Taylor DJ, Thompson CH, Kemp GJ, Barnes PR, Sanderson AL, Radda GK, Phillips DI: A relationship between impaired fetal growth and reduced muscle glycolysis revealed by 31P magnetic resonance spectroscopy. Diabetologia. 1995 Oct;38(10):1205-12. [PubMed:8690173 ]
Ferguson RA, Ball D, Krustrup P, Aagaard P, Kjaer M, Sargeant AJ, Hellsten Y, Bangsbo J: Muscle oxygen uptake and energy turnover during dynamic exercise at different contraction frequencies in humans. J Physiol. 2001 Oct 1;536(Pt 1):261-71. [PubMed:11579174 ]
Ferguson RA, Krustrup P, Kjaer M, Mohr M, Ball D, Bangsbo J: Effect of temperature on skeletal muscle energy turnover during dynamic knee-extensor exercise in humans. J Appl Physiol (1985). 2006 Jul;101(1):47-52. Epub 2006 Mar 2. [PubMed:16514001 ]
Duffield R, Dawson B, Goodman C: Energy system contribution to 1500- and 3000-metre track running. J Sports Sci. 2005 Oct;23(10):993-1002. [PubMed:16194976 ]
Hargreaves M: Skeletal muscle metabolism during exercise in humans. Clin Exp Pharmacol Physiol. 2000 Mar;27(3):225-8. [PubMed:10744352 ]
Crowther GJ, Kemper WF, Carey MF, Conley KE: Control of glycolysis in contracting skeletal muscle. II. Turning it off. Am J Physiol Endocrinol Metab. 2002 Jan;282(1):E74-9. [PubMed:11739086 ]
Preen D, Dawson B, Goodman C, Beilby J, Ching S: Creatine supplementation: a comparison of loading and maintenance protocols on creatine uptake by human skeletal muscle. Int J Sport Nutr Exerc Metab. 2003 Mar;13(1):97-111. [PubMed:12660409 ]
Raymer GH, Marsh GD, Kowalchuk JM, Thompson RT: Metabolic effects of induced alkalosis during progressive forearm exercise to fatigue. J Appl Physiol (1985). 2004 Jun;96(6):2050-6. Epub 2004 Feb 6. [PubMed:14766777 ]
Krustrup P, Mohr M, Amstrup T, Rysgaard T, Johansen J, Steensberg A, Pedersen PK, Bangsbo J: The yo-yo intermittent recovery test: physiological response, reliability, and validity. Med Sci Sports Exerc. 2003 Apr;35(4):697-705. [PubMed:12673156 ]
Iyo M, Sekine Y, Mori N: Neuromechanism of developing methamphetamine psychosis: a neuroimaging study. Ann N Y Acad Sci. 2004 Oct;1025:288-95. [PubMed:15542729 ]
Feldman EB: Creatine: a dietary supplement and ergogenic aid. Nutr Rev. 1999 Feb;57(2):45-50. [PubMed:10079702 ]

Showing NP-Card for Phosphocreatine (NP0000169)

MOL for NP0000169 (Phosphocreatine)

3D MOL for NP0000169 (Phosphocreatine)

3D SDF for NP0000169 (Phosphocreatine)

3D-SDF for NP0000169 (Phosphocreatine)

PDB for NP0000169 (Phosphocreatine)

3D PDB for NP0000169 (Phosphocreatine)

SMILES for NP0000169 (Phosphocreatine)

INCHI for NP0000169 (Phosphocreatine)

Structure for NP0000169 (Phosphocreatine)

3D Structure for NP0000169 (Phosphocreatine)