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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:51 UTC
HMDB IDHMDB01096
Secondary Accession NumbersNone
Metabolite Identification
Common NameCarbamoyl phosphate
DescriptionCarbamoyl phosphate is a precursor of both arginine and pyrimidine biosynthesis. It is a labile and potentially toxic intermediate. Carbamoyl phosphate is a molecule that is involved in ridding the body of excess nitrogen in the urea cycle, and also in the synthesis of pyrimidines. It is produced from carbon dioxide, ammonia, and phosphate (from ATP) by the enzyme carbamoyl phosphate synthase. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
Aminocarbonyl dihydrogen phosphateChEBI
Carbamic phosphoric monoanhydrideChEBI
Carbamoyl phosphateChEBI
Carbamyl phosphateChEBI
Monocarbamoyl phosphateChEBI
PHOSPHORIC ACID mono(formamide)esterChEBI
Aminocarbonyl dihydrogen phosphoric acidGenerator
Carbamoyl phosphoric acidGenerator
Carbamoyl phosphoric acidGenerator
Carbamyl phosphoric acidGenerator
Monocarbamoyl phosphoric acidGenerator
PHOSPHate mono(formamide)esterGenerator
Carbamic acid monoanhydride with phosphorateHMDB
Carbamic acid monoanhydride with phosphoric acidHMDB
Carbamoyl-PHMDB
Carbamoyl-phosphateHMDB
CarbamoylphosphateHMDB
Carbamyl-phosphateHMDB
Chemical FormulaCH4NO5P
Average Molecular Weight141.0199
Monoisotopic Molecular Weight140.982708755
IUPAC Name(carbamoyloxy)phosphonic acid
Traditional Namecarbamoyl-phosphate
CAS Registry Number590-55-6
SMILES
NC(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/CH4NO5P/c2-1(3)7-8(4,5)6/h(H2,2,3)(H2,4,5,6)
InChI KeyInChIKey=FFQKYPRQEYGKAF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organic phosphoric acids. These are organic compounds containing phosphoric acid, with the general structure OP(O)(=O)O.
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganic phosphoric acids and derivatives
Sub ClassOrganic phosphoric acids
Direct ParentOrganic phosphoric acids
Alternative Parents
Substituents
  • Organic phosphate
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Mitochondria
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.6 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.48 m3·mol-1ChemAxon
Polarizability9.12 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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
Biological Properties
Cellular Locations
  • Mitochondria
  • Endoplasmic reticulum
Biofluid Locations
  • Saliva
Tissue Location
  • Spleen
Pathways
NameSMPDB LinkKEGG Link
2-Hydroxyglutric Aciduria (D And L Form)SMP00136Not Available
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase DeficiencySMP00243Not Available
Ammonia RecyclingSMP00009map00910
Arginine and Proline MetabolismSMP00020map00330
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)SMP00362Not Available
ArgininemiaSMP00357Not Available
Argininosuccinic AciduriaSMP00003Not Available
Aspartate MetabolismSMP00067map00250
Beta Ureidopropionase DeficiencySMP00172Not Available
Canavan DiseaseSMP00175Not Available
Carbamoyl Phosphate Synthetase DeficiencySMP00002Not Available
Citrullinemia Type ISMP00001Not Available
Creatine deficiency, guanidinoacetate methyltransferase deficiencySMP00504Not Available
Dihydropyrimidinase DeficiencySMP00178Not Available
Glutamate MetabolismSMP00072map00250
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)SMP00188Not Available
HomocarnosinosisSMP00385Not Available
Hyperinsulinism-Hyperammonemia SyndromeSMP00339Not Available
Hyperornithinemia with gyrate atrophy (HOGA)SMP00505Not Available
Hyperornithinemia-hyperammonemia-homocitrullinuria [HHH-syndrome]SMP00506Not Available
Hyperprolinemia Type ISMP00361Not Available
Hyperprolinemia Type IISMP00360Not Available
HypoacetylaspartiaSMP00192Not Available
L-arginine:glycine amidinotransferase deficiencySMP00507Not Available
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy)SMP00202Not Available
Ornithine Aminotransferase Deficiency (OAT Deficiency)SMP00363Not Available
Ornithine Transcarbamylase Deficiency (OTC Deficiency)SMP00205Not Available
Prolidase Deficiency (PD)SMP00207Not Available
Prolinemia Type IISMP00208Not Available
Pyrimidine MetabolismSMP00046map00240
Succinic semialdehyde dehydrogenase deficiencySMP00567Not Available
UMP Synthase Deiciency (Orotic Aciduria)SMP00219Not Available
Urea CycleSMP00059map00330
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified12.4 +/- 14.8 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified32.1 +/- 7.53 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified33.4 +/- 10.6 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified38.4 +/- 8.24 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022424
KNApSAcK IDNot Available
Chemspider ID272
KEGG Compound IDC00169
BioCyc IDCARBAMOYL-P
BiGG ID34125
Wikipedia LinkCarbamoyl phosphate
NuGOwiki LinkHMDB01096
Metagene LinkHMDB01096
METLIN ID6002
PubChem Compound278
PDB IDCP
ChEBI ID17672
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [15890648 ]
  2. 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. [15897806 ]
  3. 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. [16780998 ]
  4. 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. [16155188 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Involved in the urea cycle of ureotelic animals where the enzyme plays an important role in removing excess ammonia from the cell.
Gene Name:
CPS1
Uniprot ID:
P31327
Molecular weight:
165649.075
Reactions
Adenosine triphosphate + Ammonia + CO(2) + Water → ADP + Phosphoric acid + Carbamoyl phosphatedetails
Adenosine triphosphate + Ammonia + Carbon dioxide + Water → ADP + Phosphoric acid + Carbamoyl phosphatedetails
General function:
Involved in carboxyl- or carbamoyltransferase activity
Specific function:
Not Available
Gene Name:
OTC
Uniprot ID:
P00480
Molecular weight:
39934.775
Reactions
Carbamoyl phosphate + Ornithine → Phosphoric acid + Citrullinedetails
General function:
Involved in hydrolase activity
Specific function:
This protein is a "fusion" protein encoding four enzymatic activities of the pyrimidine pathway (GATase, CPSase, ATCase and DHOase).
Gene Name:
CAD
Uniprot ID:
P27708
Molecular weight:
242981.73
Reactions
Adenosine triphosphate + L-Glutamine + Carbonic acid + Water → ADP + Phosphoric acid + L-Glutamic acid + Carbamoyl phosphatedetails
Carbamoyl phosphate + L-Aspartic acid → Phosphoric acid + Ureidosuccinic aciddetails