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Record Information
Version1.0
Creation Date2016-09-30 22:47:00 UTC
Update Date2020-06-04 20:14:23 UTC
BMDB IDBMDB0001511
Secondary Accession Numbers
  • BMDB01511
Metabolite Identification
Common NamePhosphocreatine
DescriptionPhosphocreatine, also known as creatine-p or neo-ton, 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. Phosphocreatine is possibly soluble (in water) and a very strong basic compound (based on its pKa). Phosphocreatine exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
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 Weight211.1131
Monoisotopic Molecular Weight211.035806957
IUPAC Name2-(N-methyl-N'-phosphonocarbamimidamido)acetic acid
Traditional Namecreatine-phosphate
CAS Registry Number67-07-2
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 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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Adipose Tissue
  • Basal Ganglia
  • Blood
  • Brain
  • Epidermis
  • Fibroblasts
  • Kidney
  • Milk
  • Neuron
  • Placenta
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Basal GangliaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified60.35 +/- 28.96 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified50 +/- 3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified46 +/- 4 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified30 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified59 +/- 4 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified49.33 +/- 52.66 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified38.24 +/- 39.15 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
HMDB IDHMDB0001511
DrugBank IDDB13191
Phenol Explorer Compound IDNot Available
FooDB IDFDB022665
KNApSAcK IDNot Available
Chemspider ID567
KEGG Compound IDC02305
BioCyc IDCREATINE-P
BiGG ID1594794
Wikipedia LinkPhosphocreatine
METLIN ID6288
PubChem Compound587
PDB IDNot Available
ChEBI ID17287
References
Synthesis ReferenceHou, Lixiang. Method for producing creatine phosphate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2004), 7 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
  2. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  3. Pan L, Yu J, Mi Z, Mo L, Jin H, Yao C, Ren D, Menghe B: A Metabolomics Approach Uncovers Differences between Traditional and Commercial Dairy Products in Buryatia (Russian Federation). Molecules. 2018 Mar 22;23(4). pii: molecules23040735. doi: 10.3390/molecules23040735. [PubMed:29565828 ]
  4. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

General function:
Involved in ATP 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 (By similarity).
Gene Name:
CKMT2
Uniprot ID:
Q3ZBP1
Molecular weight:
47231.0
General function:
Involved in ATP 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 (By similarity).
Gene Name:
CKB
Uniprot ID:
Q5EA61
Molecular weight:
42719.0
Reactions
Adenosine triphosphate + Creatine → ADP + Phosphocreatinedetails
General function:
Involved in ATP 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 (By similarity).
Gene Name:
CKMT1
Uniprot ID:
Q9TTK8
Molecular weight:
46897.0
General function:
Involved in ATP 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 (By similarity).
Gene Name:
CKM
Uniprot ID:
Q9XSC6
Molecular weight:
42989.0