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Showing Compound Phosphocreatine (FDB022665)

Record Information
Version1.0
Creation date2011-09-21 00:17:38 UTC
Update date2019-11-26 03:21:05 UTC
Primary IDFDB022665
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhosphocreatine
DescriptionPhosphocreatine 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, Nutr Rev. 1999 Feb;57(2):45-50.) [HMDB]
CAS Number67-07-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
{[imino(onoamino)methyl](methyl)amino}acetateGenerator
{[imino(onoamino)methyl](methyl)amino}acetic acidChEBI
Creatine ateChEBI
Creatine ic acidChEBI
Creatine-ateHMDB
creatine-Phmdb
creatine-phosphatehmdb
Creatineoric acidHMDB
N-(N-Onoamido)sarcosineChEBI
N-(Onoamidino)-sarcosineHMDB
N-(Onoamidino)sarcosineChEBI
N-(phosphonoamidino)-Sarcosinehmdb
N-[Imino(onoamino)methyl]-N-methyl-glycineHMDB
N-[imino(phosphonoamino)methyl]-N-methyl-Glycinehmdb
N-OcreatineChEBI
N-OrocreatineHMDB
N-OrylcreatineChEBI
N-phosphocreatinehmdb
N(Omega)-onocreatineChEBI
neo-tonhmdb
OcreatineChEBI
OrylcreatineChEBI
P-creatinehmdb
phosphocreatinehmdb
phosphorylcreatinehmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H10N3O5P
IUPAC name2-(N-methyl-N'-phosphonocarbamimidamido)acetic acid
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
Isomeric SMILESCN(CC(O)=O)C(=N)NP(O)(O)=O
Average Molecular Weight211.1131
Monoisotopic Molecular Weight211.035806957
Classification
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
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPhosphocreatine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xu-8900000000-629042926c139865eee8Spectrum
Predicted GC-MSPhosphocreatine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00y0-9450000000-df5020cc675b212f021dSpectrum
Predicted GC-MSPhosphocreatine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-3690000000-d78c9794110f04d1d6332012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-da3c0dcb3f5eaa623db12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-0b9440fbeacd93f8e2c62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0910000000-fcb05b7d59cf907f4d6b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0002-1900000000-1901e001fedfc2ec7b4b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-000b-2900000000-12f13784032f6e791b0b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-02a9-6900000000-946c0f3e6d7108360bdf2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00lr-9300000000-722ca5d041fac0c0f9532012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03dl-0900000000-6b9000773d9aa9ba14962012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-02aa21f28669c46678762012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-9200000000-1372c766f644a9c6d8fd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-0910000000-fcb05b7d59cf907f4d6b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0002-1900000000-1e02029e1cea569106e32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000b-2900000000-b5cede82b0440338b1ea2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-02a9-6900000000-946c0f3e6d7108360bdf2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00lr-9300000000-d6c9bf7b75ad1b890b8e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03dl-0900000000-90e746baee09812140422017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03dl-6930000000-d778a54d1b16d7bf961a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03dl-6940000000-fce4c19798ec230e07042017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3590000000-34c39ac175e1138311df2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lu-5900000000-026fce60f9dbc70cfa3f2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9200000000-4b05eb4ed02e14eb60292017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-3980000000-c662d51968748ca689d82017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0409-9630000000-6983e9fb7f6307837b6b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ba-9300000000-e548628e02490258e3752017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID567
ChEMBL IDCHEMBL1204644
KEGG Compound IDC02305
Pubchem Compound ID587
Pubchem Substance IDNot Available
ChEBI ID17287
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01511
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1594794
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCreatine phosphate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Creatine kinase S-type, mitochondrialCKMT2P17540
Creatine kinase B-typeCKBP12277
Creatine kinase U-type, mitochondrialCKMT1AP12532
Creatine kinase M-typeCKMP06732
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference