Phosphocreatine (CHEM022443)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:35:07 UTC
Update Date2016-11-09 01:17:30 UTC
Accession NumberCHEM022443
Identification
Common NamePhosphocreatine
ClassSmall Molecule
DescriptionPhosphocreatine - or Phosphocreatine - is the phosphorylated form of creatine. It is primarily found endogenously in the skeletal muscles of vertebrates where it serves a critical role as a rapidly acting energy buffer for muscle cell actions like contractions via its ability to regenerate adenosine triphosphate (ATP) from adenosine diphosphate (ADP).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Creatine phosphateChEBI
Creatine phosphic acidChEBI
N-(N-Phosphonoamido)sarcosineChEBI
N-(Phosphonoamidino)sarcosineChEBI
N-PhosphorylcreatineChEBI
N(Omega)-phosphonocreatineChEBI
PhosphorylcreatineChEBI
{[imino(phosphonoamino)methyl](methyl)amino}acetic acidChEBI
N-PhosphocreatineKegg
Creatine phosphoric acidGenerator
{[imino(phosphonoamino)methyl](methyl)amino}acetateGenerator
Creatine-pHMDB
Creatine-phosphateHMDB
Creatinephosphoric acidHMDB
N-(Phosphonoamidino)-sarcosineHMDB
N-PhosphorocreatineHMDB
N-[Imino(phosphonoamino)methyl]-N-methyl-glycineHMDB
Neo-tonHMDB
p-CreatineHMDB
Chemical FormulaC4H10N3O5P
Average Molecular Mass211.113 g/mol
Monoisotopic Mass211.036 g/mol
CAS Registry Number67-07-2
IUPAC Name2-(N-methyl-N'-phosphonocarbamimidamido)acetic acid
Traditional Namecreatine-phosphate
SMILESCN(CC(O)=O)C(=N)NP(O)(O)=O
InChI IdentifierInChI=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 KeyDRBBFCLWYRJSJZ-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.52 g/LALOGPS
logP-2ALOGPS
logP-2.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)-1.1ChemAxon
pKa (Strongest Basic)13.53ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area133.95 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.18 m³·mol⁻¹ChemAxon
Polarizability16.82 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xu-8900000000-629042926c139865eee8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00y0-9450000000-df5020cc675b212f021dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-3690000000-d78c9794110f04d1d633Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-da3c0dcb3f5eaa623db1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-0b9440fbeacd93f8e2c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0910000000-fcb05b7d59cf907f4d6bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0002-1900000000-1901e001fedfc2ec7b4bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000b-2900000000-12f13784032f6e791b0bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-02a9-6900000000-946c0f3e6d7108360bdfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00lr-9300000000-722ca5d041fac0c0f953Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03dl-0900000000-6b9000773d9aa9ba1496Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-02aa21f28669c4667876Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-9200000000-1372c766f644a9c6d8fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0910000000-fcb05b7d59cf907f4d6bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-1900000000-1e02029e1cea569106e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000b-2900000000-b5cede82b0440338b1eaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-02a9-6900000000-946c0f3e6d7108360bdfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00lr-9300000000-d6c9bf7b75ad1b890b8eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03dl-0900000000-90e746baee0981214042Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dl-6930000000-d778a54d1b16d7bf961aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dl-6940000000-fce4c19798ec230e0704Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3590000000-34c39ac175e1138311dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lu-5900000000-026fce60f9dbc70cfa3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-4b05eb4ed02e14eb6029Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3980000000-c662d51968748ca689d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0409-9630000000-6983e9fb7f6307837b6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ba-9300000000-e548628e02490258e375Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13191
HMDB IDHMDB0001511
FooDB IDFDB022665
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID1594794
BioCyc IDCREATINE-P
METLIN ID6288
PDB IDNot Available
Wikipedia LinkPhosphocreatine
Chemspider ID567
ChEBI ID17287
PubChem Compound ID587
Kegg Compound IDC02305
YMDB IDNot Available
ECMDB IDECMDB01511
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
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4. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
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6. 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.
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8. Skare OC, Skadberg, Wisnes AR: Creatine supplementation improves sprint performance in male sprinters. Scand J Med Sci Sports. 2001 Apr;11(2):96-102.
9. 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.
10. 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.
11. 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.
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16. 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.
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18. 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.
19. Hargreaves M: Skeletal muscle metabolism during exercise in humans. Clin Exp Pharmacol Physiol. 2000 Mar;27(3):225-8.
20. 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.
21. 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.
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23. 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.
24. 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.
25. Iyo M, Sekine Y, Mori N: Neuromechanism of developing methamphetamine psychosis: a neuroimaging study. Ann N Y Acad Sci. 2004 Oct;1025:288-95.
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27. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
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