Record Information
Version2.0
Creation Date2012-05-31 13:45:10 -0600
Update Date2015-06-03 15:53:44 -0600
Secondary Accession Numbers
  • ECMDB01096
Identification
Name:Carbamoylphosphate
DescriptionCarbamoyl 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
Thumb
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassNot Available
Direct ParentOrganic 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility15.6 g/LALOGPS
logP-1.5ALOGPS
logP-1.2ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)1.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.85 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.48 m³·mol⁻¹ChemAxon
Polarizability9.12 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
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
Adenosine triphosphate + Carbon dioxide + Ammonium <> ADP + Carbamoylphosphate +2 Hydrogen ion
Carbamoylphosphate + Ornithine + L-Ornithine <> Citrulline + Hydrogen ion + Phosphate
Adenosine triphosphate + Ammonia + Carbon dioxide <> ADP + Carbamoylphosphate
2 Adenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water <>2 ADP + Phosphate + L-Glutamate + Carbamoylphosphate
Adenosine triphosphate + Carbamic acid <> ADP + Carbamoylphosphate
Carbamoylphosphate + L-Aspartic acid <> Phosphate + Ureidosuccinic acid
Carbamoylphosphate + Ornithine <> Phosphate + Citrulline
L-Aspartic acid + Carbamoylphosphate > Hydrogen ion + Ureidosuccinic acid + Phosphate
Ammonia + Carbon dioxide + Adenosine triphosphate < Hydrogen ion + Carbamoylphosphate + ADP
Adenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water > Hydrogen ion + Carbamoylphosphate + L-Glutamate + Phosphate + ADP
Ornithine + Carbamoylphosphate <> Hydrogen ion + Citrulline + Phosphate
Oxamate + Carbamoylphosphate < Phosphate + Oxalureate
Adenosine triphosphate + Hydrogen carbonate + Ammonia > ADP + Phosphate + Carbamoylphosphate + Hydrogen ion
Adenosine triphosphate + Ammonia + Carbon dioxide > ADP + Carbamoylphosphate
2 Adenosine triphosphate + L-Glutamine + Carbonic acid + Water >2 ADP + Inorganic phosphate + L-Glutamate + Carbamoylphosphate
Carbamoylphosphate + Ornithine > Inorganic phosphate + Citrulline
Carbamoylphosphate + L-Aspartic acid > Inorganic phosphate + Ureidosuccinic acid
2 Adenosine triphosphate + L-Glutamine + Hydrogen carbonate + Water + Ammonia + Carbamic acid + Carboxyphosphate <>2 ADP + Phosphate + L-Glutamate + Carbamoylphosphate
Ornithine + Carbamoylphosphate + Ornithine > Phosphate + Hydrogen ion + Citrulline
Hydrogen carbonate + Water + L-Glutamine + 2 Adenosine triphosphate >2 Adenosine diphosphate + Phosphate + L-Glutamic acid +2 Hydrogen ion + Carbamoylphosphate +2 ADP + L-Glutamate
Carbamoylphosphate + L-Aspartic acid + L-Aspartic acid > Phosphate + Hydrogen ion + N-carbamoyl-L-aspartate
Carbamoylphosphate + ADP + 2 Hydrogen ion > Ammonium + Adenosine triphosphate + Carbon dioxide
L-Aspartic acid + Carbamoylphosphate <> Ureidosuccinic acid + Hydrogen ion + Phosphate

SMPDB Pathways:
Nitrogen metabolismPW000755 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyrimidine metabolismPW000942 ThumbThumb?image type=greyscaleThumb?image type=simple
allantoin degradation (anaerobic)PW002050 ThumbThumb?image type=greyscaleThumb?image type=simple
arginine metabolismPW000790 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-6a951539300f7f5b64d6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-1e9b8619eed467aca3ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-49d39aaea7b7b239f046View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9000000000-ff8b83b8641d1d23539fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002b-9100000000-9b7601209f4777504c50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-068148ee9b7b7acd6692View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-2eef12354837d65af0c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9200000000-df9df6c92477a4e65654View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-82163424a165525ca974View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-959c63a896bb7c629164View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI ID17672
HMDB IDHMDB01096
Pubchem Compound ID278
Kegg IDC00169
ChemSpider ID272
WikipediaCarbamoyl phosphate
BioCyc IDCARBAMOYL-P
EcoCyc IDCARBAMOYL-P
Ligand ExpoCP

Enzymes

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.
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.
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.
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.
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.
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
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
ATP + NH(3) + CO(2) = ADP + carbamoyl phosphate
Gene Name:
arcC
Uniprot ID:
P37306
Molecular weight:
31644
Reactions
ATP + NH(3) + CO(2) = ADP + carbamoyl phosphate.
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
Specific function unknown
Gene Name:
yahI
Uniprot ID:
P77624
Molecular weight:
33931
General function:
Involved in cellular amino acid biosynthetic process
Specific function:
Specific function unknown
Gene Name:
yqeA
Uniprot ID:
Q46807
Molecular weight:
33071