Bovine Metabolome Database: Showing metabocard for Phosphocreatine (BMDB0001511)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:47:00 UTC

Update Date

2020-06-04 20:14:23 UTC

BMDB ID

BMDB0001511

Secondary Accession Numbers

BMDB01511

Metabolite Identification

Common Name

Phosphocreatine

Description

Phosphocreatine, 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

MOL SDF PDB SMILES InChI

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 Molecular Weight

211.1131

Monoisotopic Molecular Weight

211.035806957

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

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 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

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
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xu-8900000000-629042926c139865eee8	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00y0-9450000000-df5020cc675b212f021d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-3690000000-d78c9794110f04d1d633	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-da3c0dcb3f5eaa623db1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-0b9440fbeacd93f8e2c6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0002-0910000000-fcb05b7d59cf907f4d6b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0002-1900000000-1901e001fedfc2ec7b4b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000b-2900000000-12f13784032f6e791b0b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-02a9-6900000000-946c0f3e6d7108360bdf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00lr-9300000000-722ca5d041fac0c0f953	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03dl-0900000000-6b9000773d9aa9ba1496	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03di-0900000000-02aa21f28669c4667876	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-9200000000-1372c766f644a9c6d8fd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-0910000000-fcb05b7d59cf907f4d6b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-1900000000-1e02029e1cea569106e3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000b-2900000000-b5cede82b0440338b1ea	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-02a9-6900000000-946c0f3e6d7108360bdf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00lr-9300000000-d6c9bf7b75ad1b890b8e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-03dl-0900000000-90e746baee0981214042	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03dl-6930000000-d778a54d1b16d7bf961a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03dl-6940000000-fce4c19798ec230e0704	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-3590000000-34c39ac175e1138311df	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lu-5900000000-026fce60f9dbc70cfa3f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9200000000-4b05eb4ed02e14eb6029	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3980000000-c662d51968748ca689d8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0409-9630000000-6983e9fb7f6307837b6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ba-9300000000-e548628e02490258e375	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
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)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Adipose Tissue
Basal Ganglia
Blood
Brain
Epidermis
Fibroblasts
Kidney
Milk
Neuron
Placenta
Skeletal Muscle
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Arginine and Proline Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Basal Ganglia	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25372282	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Milk	Detected and Quantified	60.35 +/- 28.96 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	50 +/- 3 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	46 +/- 4 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	30 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	59 +/- 4 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	49.33 +/- 52.66 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	38.24 +/- 39.15 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23738862	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Skeletal Muscle	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	All Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	High dose Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Low dose Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details

External Links

HMDB ID

HMDB0001511

DrugBank ID

DB13191

Phenol Explorer Compound ID

Not Available

FooDB 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

References

Synthesis Reference

Hou, Lixiang. Method for producing creatine phosphate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2004), 7 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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

Enzyme Details

1. Creatine kinase S-type, mitochondrial

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

Enzyme Details

2. Creatine kinase B-type

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 + Phosphocreatine	details

Enzyme Details

3. Creatine kinase U-type, mitochondrial

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

Enzyme Details

4. Creatine kinase M-type

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

Showing metabocard for Phosphocreatine (BMDB0001511)

Structure for BMDB0001511 (Phosphocreatine)

Enzymes

Reactions