Carbamoylphosphate (YMDB00082)

Identification

YMDB ID

YMDB00082

Name

Carbamoylphosphate

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Carbamoyl phosphate, also known as carbamoyl-p or phosphate, carbamyl, 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. Carbamoyl phosphate is a moderately acidic compound (based on its pKa). Carbamoyl phosphate exists in all living species, ranging from bacteria to humans. Carbamoyl phosphate is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

carbamic acid monoanhydride with phosphorate
carbamic acid monoanhydride with phosphoric acid
Carbamoyl phosphate
carbamoyl-P
carbamoyl-phosphate
Carbamoylphosphate
Carbamoylphosphic acid
carbamyl phosphate
carbamyl-phosphate
Aminocarbonyl dihydrogen phosphate
Carbamic phosphoric monoanhydride
Monocarbamoyl phosphate
Phosphoric acid mono(formamide)ester
Aminocarbonyl dihydrogen phosphoric acid
Carbamoyl phosphoric acid
Carbamyl phosphoric acid
Monocarbamoyl phosphoric acid
Phosphate mono(formamide)ester
Phosphate, carbamyl
Phosphate, carbamoyl
(Carbamoyloxy)phosphonic acid

CAS number

590-55-6

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)

IUPAC Name

(carbamoyloxy)phosphonic acid

Traditional IUPAC Name

carbamoyl-phosphate

Chemical Formula

CH₄NO₅P

SMILES

[H]OP(=O)(O[H])OC(=O)N([H])[H]

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

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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

Organoleptic Properties

Not Available

SMPDB Pathways

Nitrogen metabolism	PW002504
Pyrimidine metabolism	PW002469

KEGG Pathways

Alanine, aspartate and glutamate metabolism	ec00250
Arginine and proline metabolism	ec00330
Nitrogen metabolism	ec00910
Purine metabolism	ec00230
Pyrimidine metabolism	ec00240

SMPDB Reactions

Hydrogen carbonate + water + L-Glutamine + Adenosine triphosphate → ADP + phosphate + L-Glutamic acid + hydron + Carbamoylphosphate

Carbamoylphosphate + L-Aspartic acid → phosphate + hydron + N-Carbamoyl-L-aspartate

KEGG Reactions

L-Aspartic acid + Carbamoylphosphate → Ureidosuccinic acid + phosphate + hydron

Carbonic acid + Adenosine triphosphate + water + L-Glutamine → phosphate + L-Glutamic acid + hydron + Carbamoylphosphate + ADP

Ornithine + Carbamoylphosphate → Citrulline + phosphate + hydron

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

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

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Serre, V., Penverne, B., Souciet, J. L., Potier, S., Guy, H., Evans, D., Vicart, P., Herve, G. (2004). "Integrated allosteric regulation in the S. cerevisiae carbamylphosphate synthetase - aspartate transcarbamylase multifunctional protein." BMC Biochem 5:6.15128434
Eisenstein, E., Osborne, J. C. Jr, Chaiken, I. M., Hensley, P. (1984). "Purification and characterization of ornithine transcarbamoylase from Saccharomyces cerevisiae." J Biol Chem 259:5139-5145.6370999

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	17672
HMDB ID	HMDB01096
Pubchem Compound ID	278
Kegg ID	C00169
ChemSpider ID	272
FOODB ID	FDB022424
Wikipedia	Carbamoyl_phosphate
BioCyc ID	CARBAMOYL-P

Enzymes

Protein Details

1. Carbamoyl-phosphate synthase arginine-specific small chain

General function:: Involved in catalytic activity
Specific function:: 2 ATP + L-glutamine + HCO(3)(-) + H(2)O = 2 ADP + phosphate + L-glutamate + carbamoyl phosphate
Gene Name:: CPA1
Uniprot ID:: P07258
Molecular weight:: 45361.19922

Reactions

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

Protein Details

2. Protein URA1

General function:: Involved in carboxyl- or carbamoyltransferase activity
Specific function:: This protein is a "fusion" protein encoding three enzymatic activities of the pyrimidine pathway (GATase, CPSase, and ATCase)
Gene Name:: URA2
Uniprot ID:: P07259
Molecular weight:: 245124.0

Reactions

2 ATP + L-glutamine + HCO(3)(-) + H(2)O → 2 ADP + phosphate + L-glutamate + carbamoyl phosphate.
Carbamoyl phosphate + L-aspartate → phosphate + N-carbamoyl-L-aspartate.

Protein Details

3. Carbamoyl-phosphate synthase arginine-specific 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:: CPA2
Uniprot ID:: P03965
Molecular weight:: 123914.0

Reactions

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

Protein Details

4. Ornithine carbamoyltransferase

General function:: Involved in carboxyl- or carbamoyltransferase activity
Specific function:: Carbamoyl phosphate + L-ornithine = phosphate + L-citrulline
Gene Name:: ARG3
Uniprot ID:: P05150
Molecular weight:: 37844.80078

Reactions

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

Structure for #<Compound:0xab02d7fc>

Enzymes

Reactions

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