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Showing NP-Card for 4-methylene-2-oxoglutarate (NP0168071)

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Record Information
Version2.0
Created at2022-09-03 03:46:59 UTC
Updated at2022-09-03 03:46:59 UTC
NP-MRD IDNP0168071
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-methylene-2-oxoglutarate
Description2-Methylene-4-oxopentanedioic acid, also known as 4-carboxy-2-oxo-4-pentenoate or g-methylene-a-ketoglutaric acid, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. 2-Methylene-4-oxopentanedioic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Methylene-4-oxopentanedioic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 2-Methylene-4-oxopentanedioic acid has been detected, but not quantified in, nuts. 4-methylene-2-oxoglutarate is found in Arachis hypogaea and Lilium regale. This could make 2-methylene-4-oxopentanedioic acid a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0168071 (4-methylene-2-oxoglutarate)


  Mrv0541 02241208322D          

 11 10  0  0  0  0            999 V2000
    0.4104   -0.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4104    0.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283    0.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9856    0.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6430    0.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8895    0.1229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1499    0.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1499    1.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895   -0.9445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -0.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5748   -1.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0168071 (4-methylene-2-oxoglutarate)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.6413   -1.0007    1.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1225   -0.4646    0.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1800   -0.9310   -0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2013    0.1367   -0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138    0.9648   -1.3583 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2161    0.2506    0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2362   -0.5693    1.5629 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1719    1.2583    0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603    0.6001   -0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9761    0.9775   -0.0079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3464    1.2086   -1.6471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5890   -0.6966    1.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1082   -1.7911    1.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612   -1.3231   -1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5130   -1.7980    0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9035    1.2749   -0.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9308    1.9027   -2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  1  0
  9 10  2  0
  9  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  8  1  0
  6  7  2  0
 11 17  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  8 16  1  0
M  END
Download

3D SDF for NP0168071 (4-methylene-2-oxoglutarate)


  Mrv0541 02241208322D          

 11 10  0  0  0  0            999 V2000
    0.4104   -0.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4104    0.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283    0.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9856    0.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6430    0.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8895    0.1229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1499    0.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1499    1.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8895   -0.9445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -0.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5748   -1.3554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0168071

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O5/c1-3(5(8)9)2-4(7)6(10)11/h1-2H2,(H,8,9)(H,10,11)

> <INCHI_KEY>
OARCEFMISOKEKI-UHFFFAOYSA-N

> <FORMULA>
C6H6O5

> <MOLECULAR_WEIGHT>
158.1088

> <EXACT_MASS>
158.021523302

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
13.002898901271674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylidene-4-oxopentanedioic acid

> <ALOGPS_LOGP>
0.08

> <JCHEM_LOGP>
0.34204434966666664

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.013811031474527

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.757226329397638

> <JCHEM_PKA_STRONGEST_BASIC>
-9.761851424761067

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
33.2609

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methylene-2-oxoglutarate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0168071 (4-methylene-2-oxoglutarate)

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PDB for NP0168071 (4-methylene-2-oxoglutarate)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.766  -1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.766   0.229   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.613   0.996   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.840   0.229   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.067   0.996   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.527   0.229   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.146   0.996   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.146   2.530   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.527  -1.763   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.993  -1.303   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.073  -2.530   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    2    6    8                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    4    9   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0168071 (4-methylene-2-oxoglutarate)
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SMILES for NP0168071 (4-methylene-2-oxoglutarate)
OC(=O)C(=C)CC(=O)C(O)=O
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INCHI for NP0168071 (4-methylene-2-oxoglutarate)
InChI=1S/C6H6O5/c1-3(5(8)9)2-4(7)6(10)11/h1-2H2,(H,8,9)(H,10,11)
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View in JSmol
Synonyms
ValueSource
2-Methylidene-4-oxopentanedioic acidKegg
4-Carboxy-2-oxo-4-pentenoateKegg
2-Methylidene-4-oxopentanedioateGenerator
4-Carboxy-2-oxo-4-pentenoic acidGenerator
2-Methylene-4-oxopentanedioateGenerator
2-Methylene-4-oxoglutaric acidHMDB
g-Methylene-a-ketoglutaric acidHMDB
2-Methylene-4-oxo-pentanedioateGenerator
2-oxo-4-MethylenepentanedioateGenerator
Chemical FormulaC6H6O5
Average Mass158.1088 Da
Monoisotopic Mass158.02152 Da
IUPAC Name2-methylidene-4-oxopentanedioic acid
Traditional Name4-methylene-2-oxoglutarate
CAS Registry NumberNot Available
SMILES
OC(=O)C(=C)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C6H6O5/c1-3(5(8)9)2-4(7)6(10)11/h1-2H2,(H,8,9)(H,10,11)
InChI KeyOARCEFMISOKEKI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arachis hypogaeaLOTUS Database
Lilium regaleLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassKeto acids and derivatives  
Sub ClassGamma-keto acids and derivatives  
Direct ParentGamma-keto acids and derivatives  
Alternative Parents
Substituents
  • Gamma-keto acid
    • 

  • Branched fatty acid
    • 

  • Short-chain keto acid
    • 

  • Alpha-keto acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Unsaturated fatty acid
    • 

  • Fatty acyl
    • 

  • Alpha-hydroxy ketone
    • 

  • Ketone
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • 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
logP0.08ALOGPS
logP0.34ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.76ChemAxon
pKa (Strongest Basic)-9.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity33.26 m³·mol⁻¹ChemAxon
Polarizability13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037759  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019205  
KNApSAcK IDNot Available
Chemspider ID389673  
KEGG Compound IDC06035  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440813  
PDB IDNot Available
ChEBI ID1898  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]