ECMDB: Carbamoylphosphate (ECMDB01096) (M2MDB000253)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (9)XML

Proteins (1946)

Record Information

Version

2.0

Creation Date

2012-05-31 13:45:10 -0600

Update Date

2015-06-03 15:53:44 -0600

Secondary Accession Numbers

ECMDB01096

Identification

Name:

Carbamoylphosphate

Description

Carbamoyl phosphate is a precursor of both arginine and pyrimidine biosynthesis. It is a labile and potentially toxic intermediate. Carbamoyl phosphate is produced from carbon dioxide, ammonia, and phosphate (from ATP) by the enzyme carbamoyl phosphate synthase. -- Wikipedia

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Carbamate monoanhydride with phosphate
Carbamate monoanhydride with phosphorate
Carbamate monoanhydride with phosphoric acid
Carbamic acid monoanhydride with phosphorate
Carbamic acid monoanhydride with phosphoric acid
Carbamoyl phosphate
Carbamoyl phosphoric acid
Carbamoyl-P
Carbamoyl-phosphate
Carbamoyl-phosphoric acid
Carbamoylphosphate
Carbamoylphosphoric acid
Carbamyl phosphate
Carbamyl phosphoric acid
Carbamyl-phosphate
Carbamyl-phosphoric acid

Chemical Formula:

CH₄NO₅P

Weight:

Average: 141.0199
Monoisotopic: 140.982708755

InChI Key:

FFQKYPRQEYGKAF-UHFFFAOYSA-N

InChI:

InChI=1S/CH4NO5P/c2-1(3)7-8(4,5)6/h(H2,2,3)(H2,4,5,6)

CAS number:

590-55-6

IUPAC Name:

(carbamoyloxy)phosphonic acid

Traditional IUPAC Name:

carbamoyl-phosphate

SMILES:

NC(=O)OP(O)(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as organic phosphoric acids and derivatives. These are organic compounds containing phosphoric acid or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Not Available

Direct Parent

Organic phosphoric acids and derivatives

Alternative Parents

Substituents

Organic phosphoric acid derivative
Carboximidic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Imine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:17672 )
acyl monophosphate (CHEBI:17672 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	15.6 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-1.2	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	1.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.85 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	22.48 m³·mol⁻¹	ChemAxon
Polarizability	9.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Carbamoylphosphate + Ornithine + L-Ornithine <> Citrulline + Hydrogen ion + Phosphate
2 Adenosine triphosphate + L-Glutamine + Water + Hydrogen carbonate >2 ADP + Carbamoylphosphate + L-Glutamate +2 Hydrogen ion + Phosphate
Adenosine triphosphate + Ammonia + Carbon dioxide <> ADP + Carbamoylphosphate
Adenosine triphosphate + Carbamic acid <> ADP + Carbamoylphosphate
L-Aspartic acid + Carbamoylphosphate <> Ureidosuccinic acid + Hydrogen ion + Phosphate
2 Adenosine triphosphate + L-Glutamine + Water + Hydrogen carbonate >2 ADP + Carbamoylphosphate + L-Glutamate +2 Hydrogen ion + Phosphate

More...

SMPDB Pathways:

Nitrogen metabolism	PW000755
Pyrimidine metabolism	PW000942
allantoin degradation (anaerobic)	PW002050
arginine metabolism	PW000790

KEGG Pathways:

Alanine, aspartate and glutamate metabolism ec00250
Arginine and proline metabolism ec00330
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Nitrogen metabolism ec00910
Purine metabolism ec00230
Pyrimidine metabolism ec00240

EcoCyc Pathways:

allantoin degradation IV (anaerobic) PWY0-41
arginine biosynthesis I ARGSYN-PWY
uridine-5'-phosphate biosynthesis PWY-5686

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9100000000-6a951539300f7f5b64d6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-1e9b8619eed467aca3cc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-49d39aaea7b7b239f046	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9000000000-ff8b83b8641d1d23539f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9100000000-9b7601209f4777504c50	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-068148ee9b7b7acd6692	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-2eef12354837d65af0c1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9200000000-df9df6c92477a4e65654	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-82163424a165525ca974	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-959c63a896bb7c629164	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Chen KF, Lai YY, Sun HS, Tsai SJ: Transcriptional repression of human cad gene by hypoxia inducible factor-1alpha. Nucleic Acids Res. 2005 Sep 9;33(16):5190-8. Print 2005. Pubmed: 16155188
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Schnater JM, Bruder E, Bertschin S, Woodtli T, de Theije C, Pietsch T, Aronson DC, von Schweinitz D, Lamers WH, Kohler ES: Subcutaneous and intrahepatic growth of human hepatoblastoma in immunodeficient mice. J Hepatol. 2006 Sep;45(3):377-86. Epub 2006 May 3. Pubmed: 16780998
Sigoillot FD, Kotsis DH, Serre V, Sigoillot SM, Evans DR, Guy HI: Nuclear localization and mitogen-activated protein kinase phosphorylation of the multifunctional protein CAD. J Biol Chem. 2005 Jul 8;280(27):25611-20. Epub 2005 May 12. Pubmed: 15890648
Struck J, Uhlein M, Morgenthaler NG, Furst W, Hoflich C, Bahrami S, Bergmann A, Volk HD, Redl H: Release of the mitochondrial enzyme carbamoyl phosphate synthase under septic conditions. Shock. 2005 Jun;23(6):533-8. Pubmed: 15897806
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17672
HMDB ID	HMDB01096
Pubchem Compound ID	278
Kegg ID	C00169
ChemSpider ID	272
Wikipedia	Carbamoyl phosphate
BioCyc ID	CARBAMOYL-P
EcoCyc ID	CARBAMOYL-P
Ligand Expo	CP

Enzymes

Protein Details

1. Carbamoyl-phosphate synthase large chain

General function:: Involved in ATP binding
Specific function:: 2 ATP + L-glutamine + HCO(3)(-) + H(2)O = 2 ADP + phosphate + L-glutamate + carbamoyl phosphate
Gene Name:: carB
Uniprot ID:: P00968
Molecular weight:: 117841

Reactions

2 ATP + L-glutamine + HCO(3)(-) + H(2)O = 2 ADP + phosphate + L-glutamate + carbamoyl phosphate.

Protein Details

2. Ornithine carbamoyltransferase chain I

General function:: Involved in carboxyl- or carbamoyltransferase activity
Specific function:: Carbamoyl phosphate + L-ornithine = phosphate + L-citrulline
Gene Name:: argI
Uniprot ID:: P04391
Molecular weight:: 36907

Reactions

Carbamoyl phosphate + L-ornithine = phosphate + L-citrulline.

Protein Details

3. Ornithine carbamoyltransferase chain F

General function:: Involved in carboxyl- or carbamoyltransferase activity
Specific function:: Carbamoyl phosphate + L-ornithine = phosphate + L-citrulline
Gene Name:: argF
Uniprot ID:: P06960
Molecular weight:: 36827

Reactions

Carbamoyl phosphate + L-ornithine = phosphate + L-citrulline.

Protein Details

4. Carbamoyl-phosphate synthase small chain

General function:: Involved in glutamine catabolic process
Specific function:: 2 ATP + L-glutamine + HCO(3)(-) + H(2)O = 2 ADP + phosphate + L-glutamate + carbamoyl phosphate
Gene Name:: carA
Uniprot ID:: P0A6F1
Molecular weight:: 41431

Reactions

2 ATP + L-glutamine + HCO(3)(-) + H(2)O = 2 ADP + phosphate + L-glutamate + carbamoyl phosphate.

Protein Details

5. Aspartate carbamoyltransferase catalytic chain

General function:: Involved in carboxyl- or carbamoyltransferase activity
Specific function:: Carbamoyl phosphate + L-aspartate = phosphate + N-carbamoyl-L-aspartate
Gene Name:: pyrB
Uniprot ID:: P0A786
Molecular weight:: 34427

Reactions

Carbamoyl phosphate + L-aspartate = phosphate + N-carbamoyl-L-aspartate.

Protein Details

6. Aspartate carbamoyltransferase regulatory chain

General function:: Involved in 'de novo' pyrimidine base biosynthetic process
Specific function:: Involved in allosteric regulation of aspartate carbamoyltransferase
Gene Name:: pyrI
Uniprot ID:: P0A7F3
Molecular weight:: 17121

Protein Details

7. Carbamate kinase