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Showing NP-Card for Carboxyphosphoenolpyruvate (NP0050519)

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Record Information
Version2.0
Created at2022-04-27 21:47:00 UTC
Updated at2022-04-27 21:47:00 UTC
NP-MRD IDNP0050519
Secondary Accession NumbersNone
Natural Product Identification
Common NameCarboxyphosphoenolpyruvate
Description1-Carboxyvinyl carboxyphosphonate, also known as carboxyphosphonoenolpyruvate, belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid. 1-Carboxyvinyl carboxyphosphonate is an extremely strong acidic compound (based on its pKa). Carboxyphosphoenolpyruvate is found in Streptomyces hygroscopicus. An organic phosphonate having O-1-carboxyvinyl and C-carboxy substituents.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050519 (Carboxyphosphoenolpyruvate)


  Mrv1533004171500542D          

 12 11  0  0  0  0            999 V2000
    1.2375    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
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3D MOL for NP0050519 (Carboxyphosphoenolpyruvate)

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3D SDF for NP0050519 (Carboxyphosphoenolpyruvate)

  Mrv1533004171500542D          

 12 11  0  0  0  0            999 V2000
    1.2375    3.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050519

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(=C)OP(O)(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H5O7P/c1-2(3(5)6)11-12(9,10)4(7)8/h1H2,(H,5,6)(H,7,8)(H,9,10)

> <INCHI_KEY>
LPUFGTSGSICQBX-UHFFFAOYSA-N

> <FORMULA>
C4H5O7P

> <MOLECULAR_WEIGHT>
196.051

> <EXACT_MASS>
195.977289499

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.945565761563177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[carboxy(hydroxy)phosphoryl]oxy}prop-2-enoic acid

> <ALOGPS_LOGP>
-0.50

> <JCHEM_LOGP>
-0.4988733220000001

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.07958138776133

> <JCHEM_PKA_STRONGEST_ACIDIC>
-0.9326264444317838

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
34.5529

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
carboxyphosphonoenolpyruvate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050519 (Carboxyphosphoenolpyruvate)
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PDB for NP0050519 (Carboxyphosphoenolpyruvate)
HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       2.310   6.668   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.080   5.335   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.620   5.335   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770   4.001   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.080   2.667   0.000  0.00  0.00           O+0
HETATM    7  P   UNK     0       2.310   1.334   0.000  0.00  0.00           P+0
HETATM    8  O   UNK     0       0.976   2.104   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.644   0.564   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0050519 (Carboxyphosphoenolpyruvate)
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SMILES for NP0050519 (Carboxyphosphoenolpyruvate)
OC(=O)C(=C)OP(O)(=O)C(O)=O
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INCHI for NP0050519 (Carboxyphosphoenolpyruvate)
InChI=1S/C4H5O7P/c1-2(3(5)6)11-12(9,10)4(7)8/h1H2,(H,5,6)(H,7,8)(H,9,10)
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Synonyms
ValueSource
CarboxyphosphonoenolpyruvateChEBI
Carboxyphosphonoenolpyruvic acidGenerator
1-Carboxyvinyl carboxyphosphonic acidGenerator
Chemical FormulaC4H5O7P
Average Mass196.0510 Da
Monoisotopic Mass195.97729 Da
IUPAC Name2-{[carboxy(hydroxy)phosphoryl]oxy}prop-2-enoic acid
Traditional Namecarboxyphosphonoenolpyruvate
CAS Registry NumberNot Available
SMILES
OC(=O)C(=C)OP(O)(=O)C(O)=O
InChI Identifier
InChI=1S/C4H5O7P/c1-2(3(5)6)11-12(9,10)4(7)8/h1H2,(H,5,6)(H,7,8)(H,9,10)
InChI KeyLPUFGTSGSICQBX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces hygroscopicusBacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassOrganic phosphonic acids and derivatives  
Sub ClassOrganic phosphonic acids  
Direct ParentOrganic phosphonic acids  
Alternative Parents
Substituents
  • Organophosphonic acid
    • 

  • Carbonic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organophosphorus compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.5ALOGPS
logP-0.5ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)-0.93ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.55 m³·mol⁻¹ChemAxon
Polarizability13.95 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000783  
Chemspider IDNot Available
KEGG Compound IDC06367  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound360637  
PDB IDNot Available
ChEBI ID17056  
Good Scents IDNot Available
References
General ReferencesNot Available