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Showing metabocard for Carbamoyl phosphate (HMDB0001096)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-30 19:00:55 UTC
HMDB IDHMDB0001096
Secondary Accession Numbers
  • HMDB01096
Metabolite Identification
Common NameCarbamoyl phosphate
DescriptionCarbamoyl 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. Within humans, carbamoyl phosphate participates in a number of enzymatic reactions. In particular, carbamoyl phosphate can be biosynthesized from L-glutamine and hydrogen carbonate through the action of the enzyme cad protein. In addition, carbamoyl phosphate can be converted into ureidosuccinic acid through the action of the enzyme cad protein. Its enzymatic counterpart, carbamoyl phosphate synthetase I (CPS I), interacts with a class of molecules called sirtuins, NAD dependent protein deacetylases, and ATP to form carbamoyl phosphate. It is produced from bicarbonate, ammonia (derived from amino acids), and phosphate (from ATP). In humans, carbamoyl phosphate is involved in the metabolic disorder called the beta-ureidopropionase deficiency pathway. Outside of the human body, Carbamoyl phosphate has been detected, but not quantified in, several different foods, such as cucurbita, peanuts, common oregano, figs, and chinese water chestnuts. This could make carbamoyl phosphate a potential biomarker for the consumption of these foods. Carbamoyl phosphate is a potentially toxic compound. CP then enters the urea cycle in which it reacts with ornithine (a process catalyzed by the enzyme ornithine transcarbamylase) to form citrulline. A defect in the CPS I enzyme, and a subsequent deficiency in the production of carbamoyl phosphate has been linked to hyper-ammonemia in humans. In land-dwelling animals, it is an intermediary metabolite in nitrogen disposal through the urea cycle and the synthesis of pyrimidines. Carbamoyl phosphate is an anion of biochemical significance.
Structure
Data?1593543654
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001096 (Carbamoyl phosphate)


  Mrv1652306302020592D          

  8  7  0  0  0  0            999 V2000
 9995.9490 9996.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6644 9995.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3777 9996.0400    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0993 9995.6401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9654 9996.7554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7900 9996.7554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2356 9995.6264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9475 9996.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  3  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  2  0  0  0  0
M  END
Download

3D MOL for HMDB0001096 (Carbamoyl phosphate)

Download
3D SDF for HMDB0001096 (Carbamoyl phosphate)

  Mrv1652306302020592D          

  8  7  0  0  0  0            999 V2000
 9995.9490 9996.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6644 9995.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3777 9996.0400    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0993 9995.6401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.9654 9996.7554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.7900 9996.7554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.2356 9995.6264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9475 9996.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  3  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001096

> <DATABASE_NAME>
hmdb

> <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_KEY>
FFQKYPRQEYGKAF-UHFFFAOYSA-N

> <FORMULA>
CH4NO5P

> <MOLECULAR_WEIGHT>
141.0199

> <EXACT_MASS>
140.982708755

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
9.115059988547511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(carbamoyloxy)phosphonic acid

> <ALOGPS_LOGP>
-1.52

> <JCHEM_LOGP>
-1.2107563936666663

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.126245825395335

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1011909792872663

> <JCHEM_POLAR_SURFACE_AREA>
109.85

> <JCHEM_REFRACTIVITY>
22.4801

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carbamoyl-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0001096 (Carbamoyl phosphate)
https://cactus.nci.nih.gov/chemical/structure/NC(=O)OP(O)(O)=O/file?format=sd...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:11})
 12 11  0  0  0  0  0  0  0  0999 V2000
    2.8234   -0.6802   -0.0986 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6168   -0.0870   -0.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5416    1.1150    0.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4948   -0.8264   -0.0901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9072   -0.0439    0.0311 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0753    0.9532   -1.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1162   -1.1069    0.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9295    0.7361    1.2887 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6317   -0.1476   -0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8835   -1.6403   -0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0696    0.5096   -2.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9929   -0.7050    0.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  0  0  0  0
M  END
$$$$

Download
PDB for HMDB0001096 (Carbamoyl phosphate)
HEADER    PROTEIN                                 30-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-20         0                                  
HETATM    1  C   UNK     0    8659.1058659.275   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8660.4408658.507   0.000  0.00  0.00           O+0
HETATM    3  P   UNK     0    8661.7728659.275   0.000  0.00  0.00           P+0
HETATM    4  O   UNK     0    8663.1198658.528   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8661.0028660.610   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8662.5418660.610   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8657.7738658.503   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8659.1028660.814   0.000  0.00  0.00           O+0
CONECT    1    2    7    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    1                                                            
CONECT    8    1                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

Download
3D PDB for HMDB0001096 (Carbamoyl phosphate)
COMPND    https://cactus.nci.nih.gov/chemical/structure/NC(=O)OP(O)(O)=O/file?format=sd... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  N   UNL     1       2.823  -0.680  -0.099  1.00  0.00           N  
HETATM    2  C   UNL     1       1.617  -0.087  -0.005  1.00  0.00           C  
HETATM    3  O   UNL     1       1.542   1.115   0.156  1.00  0.00           O  
HETATM    4  O   UNL     1       0.495  -0.826  -0.090  1.00  0.00           O  
HETATM    5  P   UNL     1      -0.907  -0.044   0.031  1.00  0.00           P  
HETATM    6  O   UNL     1      -1.075   0.953  -1.222  1.00  0.00           O  
HETATM    7  O   UNL     1      -2.116  -1.107   0.037  1.00  0.00           O  
HETATM    8  O   UNL     1      -0.929   0.736   1.289  1.00  0.00           O  
HETATM    9  H   UNL     1       3.632  -0.148  -0.037  1.00  0.00           H  
HETATM   10  H   UNL     1       2.884  -1.640  -0.223  1.00  0.00           H  
HETATM   11  H   UNL     1      -1.070   0.510  -2.081  1.00  0.00           H  
HETATM   12  H   UNL     1      -2.993  -0.705   0.108  1.00  0.00           H  
CONECT    1    2    9   10                                            
CONECT    2    1    3    3    4                                       
CONECT    3    2    2                                                 
CONECT    4    2    5                                                 
CONECT    5    4    6    7    8                                       
CONECT    5    8                                                      
CONECT    6    5   11                                                 
CONECT    7    5   12                                                 
CONECT    8    5    5                                                 
CONECT    9    1                                                      
CONECT   10    1                                                      
CONECT   11    6                                                      
CONECT   12    7                                                      
MASTER        0    0    0    0    0    0    0    0   12    0   12    0
END

Download
SMILES for HMDB0001096 (Carbamoyl phosphate)
NC(=O)OP(O)(O)=O
Download
INCHI for HMDB0001096 (Carbamoyl phosphate)
InChI=1S/CH4NO5P/c2-1(3)7-8(4,5)6/h(H2,2,3)(H2,4,5,6)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Aminocarbonyl dihydrogen phosphateChEBI
Carbamic phosphoric monoanhydrideChEBI
Carbamyl phosphateChEBI
Monocarbamoyl phosphateChEBI
Phosphoric acid mono(formamide)esterChEBI
Aminocarbonyl dihydrogen 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
Phosphate, carbamylMeSH, HMDB
Phosphate, carbamoylMeSH, HMDB
(Carbamoyloxy)phosphonic acidHMDB
Carbamoyl 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 KeyFFQKYPRQEYGKAF-UHFFFAOYSA-N
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
Ontology
Disposition
Route of exposure:
Source:
Biological location:
Process
Naturally occurring process:
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 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9100000000-6a951539300f7f5b64d62016-09-22View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-36b48b4fe887b88869d12021-09-05View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0002-9000000000-1e9b8619eed467aca3cc2015-05-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0002-9000000000-49d39aaea7b7b239f0462015-05-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-0005-9000000000-ff8b83b8641d1d23539f2015-05-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-002b-9100000000-9b7601209f4777504c502015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-004i-9000000000-068148ee9b7b7acd66922015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-004i-9000000000-2eef12354837d65af0c12015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0002-9200000000-df9df6c92477a4e656542021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0002-9000000000-82163424a165525ca9742021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-0006-9000000000-959c63a896bb7c6291642021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Mitochondria
    • 

  • Endoplasmic reticulum
Biospecimen Locations
  • Saliva
Tissue Locations
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FooDB IDFDB022424  
KNApSAcK IDC00007513  
Chemspider ID272  
KEGG Compound IDC00169  
BioCyc IDCARBAMOYL-P  
BiGG ID34125  
Wikipedia LinkCarbamoyl phosphate  
METLIN ID6002  
PubChem Compound278  
PDB IDNot Available
ChEBI ID17672  
Food Biomarker OntologyNot Available
VMH IDCBP  
MarkerDB IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:16155188  ] 
Enzymes
  Enzyme Details
1. Carbamoyl-phosphate synthase [ammonia], mitochondrial
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 + Phosphate + Carbamoyl phosphatedetails
Adenosine triphosphate + Ammonia + Carbon dioxide + Water → ADP + Phosphate + Carbamoyl phosphatedetails
  Enzyme Details
2. Ornithine carbamoyltransferase, mitochondrial
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 → Phosphate + Citrullinedetails
  Enzyme Details
3. CAD protein
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 + Hydrogen carbonate + Water → ADP + Phosphate + L-Glutamic acid + Carbamoyl phosphatedetails
Carbamoyl phosphate + L-Aspartic acid → Phosphate + Ureidosuccinic aciddetails