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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:18:59 UTC

Update Date

2022-03-07 02:57:06 UTC

HMDB ID

HMDB0041624

Secondary Accession Numbers

HMDB41624

Metabolite Identification

Common Name

Phosphocreatinine

Description

Phosphocreatinine 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. Phosphocreatinine is found, on average, in the highest concentration within milk (cow). This could make phosphocreatinine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Phosphocreatinine.

Structure

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

HEADER    PROTEIN                                 25-JUN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JUN-18         0                                  
HETATM    1  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      -0.615  -1.536   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.637  -4.349   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.396  -3.569   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.418  -2.316   0.000  0.00  0.00           O+0
HETATM   12  P   UNK     0       0.011  -2.943   0.000  0.00  0.00           P+0
CONECT    1    7                                                            
CONECT    2    3    7                                                       
CONECT    3    2    5    8                                                  
CONECT    4    5    6    7                                                  
CONECT    5    3    4                                                       
CONECT    6    4   12                                                       
CONECT    7    1    2    4                                                  
CONECT    8    3                                                            
CONECT    9   12                                                            
CONECT   10   12                                                            
CONECT   11   12                                                            
CONECT   12    6    9   10   11                                             
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Phosphocreatinine, disodium salt	HMDB
Phosphocreatinine, magnesium (1+) salt	HMDB
Phosphocreatinine	MeSH

Chemical Formula

C₄H₈N₃O₄P

Average Molecular Weight

193.0978

Monoisotopic Molecular Weight

193.025242271

IUPAC Name

[(4-hydroxy-1-methyl-2,5-dihydro-1H-imidazol-2-ylidene)amino]phosphonic acid

Traditional Name

phosphocreatinine

CAS Registry Number

Not Available

SMILES

CN1CC(=O)NC1=NP(O)(O)=O

InChI Identifier

InChI=1S/C4H8N3O4P/c1-7-2-3(8)5-4(7)6-12(9,10)11/h2H2,1H3,(H3,5,6,8,9,10,11)

InChI Key

HIPLEPXPNLWKCQ-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
Imidazolinone
Organic phosphoric acid derivative
2-imidazoline
Guanidine
N-acylimine
Azacycle
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041624)
Cytoplasm (HMDB: HMDB0041624)

Source

Exogenous

Exogenous (HMDB: HMDB0041624)

Food

Food (HMDB: HMDB0041624)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041624)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	12.3 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-2.6	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	-4.3	ChemAxon
pKa (Strongest Basic)	8.32	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.72 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40.01 m³·mol⁻¹	ChemAxon
Polarizability	15.66 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.27	31661259
DarkChem	[M-H]-	135.768	31661259
DeepCCS	[M+H]+	130.148	30932474
DeepCCS	[M-H]-	126.319	30932474
DeepCCS	[M-2H]-	163.733	30932474
DeepCCS	[M+Na]+	139.259	30932474
AllCCS	[M+H]+	140.6	32859911
AllCCS	[M+H-H2O]+	136.5	32859911
AllCCS	[M+NH4]+	144.4	32859911
AllCCS	[M+Na]+	145.4	32859911
AllCCS	[M-H]-	133.0	32859911
AllCCS	[M+Na-2H]-	134.1	32859911
AllCCS	[M+HCOO]-	135.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phosphocreatinine	CN1CC(=O)NC1=NP(O)(O)=O	3206.2	Standard polar	33892256
Phosphocreatinine	CN1CC(=O)NC1=NP(O)(O)=O	2055.4	Standard non polar	33892256
Phosphocreatinine	CN1CC(=O)NC1=NP(O)(O)=O	2223.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phosphocreatinine,1TMS,isomer #1	CN1CC(=O)NC1=NP(=O)(O)O[Si](C)(C)C	2061.0	Semi standard non polar	33892256
Phosphocreatinine,1TMS,isomer #1	CN1CC(=O)NC1=NP(=O)(O)O[Si](C)(C)C	1900.9	Standard non polar	33892256
Phosphocreatinine,1TMS,isomer #2	CN1CC(=O)N([Si](C)(C)C)C1=NP(=O)(O)O	1940.0	Semi standard non polar	33892256
Phosphocreatinine,1TMS,isomer #2	CN1CC(=O)N([Si](C)(C)C)C1=NP(=O)(O)O	1817.7	Standard non polar	33892256
Phosphocreatinine,2TMS,isomer #1	CN1CC(=O)NC1=NP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2089.4	Semi standard non polar	33892256
Phosphocreatinine,2TMS,isomer #1	CN1CC(=O)NC1=NP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1998.9	Standard non polar	33892256
Phosphocreatinine,2TMS,isomer #2	CN1CC(=O)N([Si](C)(C)C)C1=NP(=O)(O)O[Si](C)(C)C	1940.9	Semi standard non polar	33892256
Phosphocreatinine,2TMS,isomer #2	CN1CC(=O)N([Si](C)(C)C)C1=NP(=O)(O)O[Si](C)(C)C	1895.1	Standard non polar	33892256
Phosphocreatinine,3TMS,isomer #1	CN1CC(=O)N([Si](C)(C)C)C1=NP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1982.9	Semi standard non polar	33892256
Phosphocreatinine,3TMS,isomer #1	CN1CC(=O)N([Si](C)(C)C)C1=NP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1979.4	Standard non polar	33892256
Phosphocreatinine,1TBDMS,isomer #1	CN1CC(=O)NC1=NP(=O)(O)O[Si](C)(C)C(C)(C)C	2304.2	Semi standard non polar	33892256
Phosphocreatinine,1TBDMS,isomer #1	CN1CC(=O)NC1=NP(=O)(O)O[Si](C)(C)C(C)(C)C	2120.4	Standard non polar	33892256
Phosphocreatinine,1TBDMS,isomer #2	CN1CC(=O)N([Si](C)(C)C(C)(C)C)C1=NP(=O)(O)O	2209.5	Semi standard non polar	33892256
Phosphocreatinine,1TBDMS,isomer #2	CN1CC(=O)N([Si](C)(C)C(C)(C)C)C1=NP(=O)(O)O	2060.5	Standard non polar	33892256
Phosphocreatinine,2TBDMS,isomer #1	CN1CC(=O)NC1=NP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2501.1	Semi standard non polar	33892256
Phosphocreatinine,2TBDMS,isomer #1	CN1CC(=O)NC1=NP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2406.6	Standard non polar	33892256
Phosphocreatinine,2TBDMS,isomer #2	CN1CC(=O)N([Si](C)(C)C(C)(C)C)C1=NP(=O)(O)O[Si](C)(C)C(C)(C)C	2344.8	Semi standard non polar	33892256
Phosphocreatinine,2TBDMS,isomer #2	CN1CC(=O)N([Si](C)(C)C(C)(C)C)C1=NP(=O)(O)O[Si](C)(C)C(C)(C)C	2333.7	Standard non polar	33892256
Phosphocreatinine,3TBDMS,isomer #1	CN1CC(=O)N([Si](C)(C)C(C)(C)C)C1=NP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2511.2	Semi standard non polar	33892256
Phosphocreatinine,3TBDMS,isomer #1	CN1CC(=O)N([Si](C)(C)C(C)(C)C)C1=NP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2596.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphocreatinine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9600000000-3fca30e39bef8c85ebd4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphocreatinine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phosphocreatinine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 10V, Positive-QTOF	splash10-0006-2900000000-b62e4e2c35249fb5e580	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 20V, Positive-QTOF	splash10-03mj-9800000000-ced790d0981cfdb22436	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 40V, Positive-QTOF	splash10-0005-9000000000-3123f023cc112c230880	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 10V, Negative-QTOF	splash10-0006-2900000000-27fce4638ad5139cbc8e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 20V, Negative-QTOF	splash10-0006-9000000000-2d46701781bab3282a80	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 40V, Negative-QTOF	splash10-004l-9300000000-ffc3f79e36d0aac37c18	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 10V, Negative-QTOF	splash10-0006-0900000000-6f97dd1de59246efd10e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 20V, Negative-QTOF	splash10-0006-2900000000-10ed0e82979953cac818	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 40V, Negative-QTOF	splash10-0096-9300000000-fcb9f4f98f0d6c160528	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 10V, Positive-QTOF	splash10-0006-0900000000-2a944ed8ccceced51bc4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 20V, Positive-QTOF	splash10-03dl-1900000000-397496017366ed258e26	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phosphocreatinine 40V, Positive-QTOF	splash10-0007-9000000000-01d4161723ec428f3257	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021786

KNApSAcK ID

Not Available

Chemspider ID

64349

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71214

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
Iyengar MR, Coleman DW, Butler TM: Phosphocreatinine, a high-energy phosphate in muscle, spontaneously forms phosphocreatine and creatinine under physiological conditions. J Biol Chem. 1985 Jun 25;260(12):7562-7. [PubMed:3997888 ]

Showing metabocard for Phosphocreatinine (HMDB0041624)

MOL for HMDB0041624 (Phosphocreatinine)

3D MOL for HMDB0041624 (Phosphocreatinine)

3D SDF for HMDB0041624 (Phosphocreatinine)

3D-SDF for HMDB0041624 (Phosphocreatinine)

PDB for HMDB0041624 (Phosphocreatinine)

3D PDB for HMDB0041624 (Phosphocreatinine)

SMILES for HMDB0041624 (Phosphocreatinine)

INCHI for HMDB0041624 (Phosphocreatinine)

Structure for HMDB0041624 (Phosphocreatinine)

3D Structure for HMDB0041624 (Phosphocreatinine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra