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Showing NP-Card for 4-Oxalocrotonate (NP0055002)

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Record Information
Version2.0
Created at2022-04-28 01:10:48 UTC
Updated at2022-04-28 01:10:49 UTC
NP-MRD IDNP0055002
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Oxalocrotonate
Description4-Oxalocrotonic acid belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 4-Oxalocrotonate is found in Pseudomonas pseudoalcaligenes. 4-Oxalocrotonate was first documented in 2006 (PMID: 17090920). Based on a literature review very few articles have been published on 4-oxalocrotonic acid.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0055002 (4-Oxalocrotonate)


  Mrv1652304282203102D          

 11 10  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   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
    0.0000   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  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
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
Download

3D MOL for NP0055002 (4-Oxalocrotonate)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
    3.3972   -0.3831   -1.3379 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576    0.1656   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8628    0.7665    0.5552 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5031    0.1699    0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6506   -0.3983   -0.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7788   -0.4967   -0.6839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620    0.0836    0.4587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9930    0.7025    1.4334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9349   -0.0695    0.4938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5304   -0.6750   -0.4320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7209    0.4213    1.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6340    0.2072    0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412    0.6436    0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128   -0.8692   -1.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1795   -1.5415   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968    0.0394   -1.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4630    1.2337    2.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 11  1  0
  9 10  2  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  6 15  1  0
  6 16  1  0
 11 17  1  0
M  END
Download

3D SDF for NP0055002 (4-Oxalocrotonate)


  Mrv1652304282203102D          

 11 10  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -1.4289    0.0000 O   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
    0.0000   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  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
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055002

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)\C=C\CC(=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O5/c7-4(6(10)11)2-1-3-5(8)9/h1,3H,2H2,(H,8,9)(H,10,11)/b3-1+

> <INCHI_KEY>
OOEDHTCVMHDXRH-HNQUOIGGSA-N

> <FORMULA>
C6H6O5

> <MOLECULAR_WEIGHT>
158.109

> <EXACT_MASS>
158.021523293

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.264496391583386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-5-oxohex-2-enedioic acid

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
0.33312885500000006

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.082996035828588

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.765430103976882

> <JCHEM_PKA_STRONGEST_BASIC>
-9.745204213664453

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
34.5773

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-oxohex-2-enedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0055002 (4-Oxalocrotonate)

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PDB for NP0055002 (4-Oxalocrotonate)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -5.335   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.310  -4.001   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0055002 (4-Oxalocrotonate)
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SMILES for NP0055002 (4-Oxalocrotonate)
OC(=O)\C=C\CC(=O)C(O)=O
Download
INCHI for NP0055002 (4-Oxalocrotonate)
InChI=1S/C6H6O5/c7-4(6(10)11)2-1-3-5(8)9/h1,3H,2H2,(H,8,9)(H,10,11)/b3-1+
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View in JSmol
Synonyms
ValueSource
4-OxalocrotonateGenerator
OxalocrotonateMeSH
Chemical FormulaC6H6O5
Average Mass158.1090 Da
Monoisotopic Mass158.02152 Da
IUPAC Name(2E)-5-oxohex-2-enedioic acid
Traditional Name(2E)-5-oxohex-2-enedioic acid
CAS Registry NumberNot Available
SMILES
OC(=O)\C=C\CC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H6O5/c7-4(6(10)11)2-1-3-5(8)9/h1,3H,2H2,(H,8,9)(H,10,11)/b3-1+
InChI KeyOOEDHTCVMHDXRH-HNQUOIGGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pseudomonas pseudoalcaligenesBacteria
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12  carbon atoms long side chain.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassKeto acids and derivatives  
Sub ClassMedium-chain keto acids and derivatives  
Direct ParentMedium-chain keto acids and derivatives  
Alternative Parents
Substituents
  • Medium-chain keto acid
    • 

  • Fatty acyl
    • 

  • Unsaturated fatty acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Alpha-keto acid
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP0.04ALOGPS
logP0.33ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.77ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.58 m³·mol⁻¹ChemAxon
Polarizability13.26 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 IDC00007534  
Chemspider ID4697481  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5773667  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Orii C, Takenaka S, Murakami S, Aoki K: Metabolism of 4-amino-3-hydroxybenzoic acid by Bordetella sp. strain 10d: A different modified meta-cleavage pathway for 2-aminophenols. Biosci Biotechnol Biochem. 2006 Nov;70(11):2653-61. doi: 10.1271/bbb.60264. Epub  2006 Nov 7. [PubMed:17090920  ]