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Showing NP-Card for 2-oxobut-3-enoic acid (NP0296000)

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Record Information
Version2.0
Created at2022-09-10 05:19:44 UTC
Updated at2022-09-10 05:19:44 UTC
NP-MRD IDNP0296000
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-oxobut-3-enoic acid
Description2-Oxobut-3-enoic acid, also known as vinylglyoxylate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. 2-Oxobut-3-enoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 2-oxobut-3-enoic acid is found in Trypanosoma brucei. 2-oxobut-3-enoic acid was first documented in 2005 (PMID: 15592827). Based on a literature review a small amount of articles have been published on 2-oxobut-3-enoic acid (PMID: 26102233) (PMID: 18312570).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0296000 (2-oxobut-3-enoic acid)


  Mrv1652309102207192D          

  7  6  0  0  0  0            999 V2000
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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    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  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
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3D MOL for NP0296000 (2-oxobut-3-enoic acid)

     RDKit          3D

 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.8111    0.1070   -0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0151   -0.6822    0.2364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3729   -0.4716    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487   -1.3726    1.0942 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1076    0.6685   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5573    1.5845   -0.6523 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    0.7235    0.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5207    1.0266   -0.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872   -0.1432   -0.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4542   -1.6148    0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1097    0.1741   -0.3188 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0
  5  6  2  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  7 11  1  0
  2 10  1  0
  1  8  1  0
  1  9  1  0
M  END
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3D SDF for NP0296000 (2-oxobut-3-enoic acid)


  Mrv1652309102207192D          

  7  6  0  0  0  0            999 V2000
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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    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  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296000

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H4O3/c1-2-3(5)4(6)7/h2H,1H2,(H,6,7)

> <INCHI_KEY>
DGUBLKUCHAAUFT-UHFFFAOYSA-N

> <FORMULA>
C4H4O3

> <MOLECULAR_WEIGHT>
100.073

> <EXACT_MASS>
100.016043989

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
8.49955767996209

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxobut-3-enoic acid

> <JCHEM_LOGP>
0.8221669603333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.003861107243324

> <JCHEM_PKA_STRONGEST_BASIC>
-9.899050376356636

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
22.6374

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-oxobut-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0296000 (2-oxobut-3-enoic acid)

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PDB for NP0296000 (2-oxobut-3-enoic acid)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0296000 (2-oxobut-3-enoic acid)
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SMILES for NP0296000 (2-oxobut-3-enoic acid)
OC(=O)C(=O)C=C
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INCHI for NP0296000 (2-oxobut-3-enoic acid)
InChI=1S/C4H4O3/c1-2-3(5)4(6)7/h2H,1H2,(H,6,7)
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View in JSmol
Synonyms
ValueSource
VinylglyoxylateChEBI
Vinylglyoxylic acidGenerator
2-Oxobut-3-enoateGenerator
2-oxo-3-Butenoic acidMeSH
Chemical FormulaC4H4O3
Average Mass100.0730 Da
Monoisotopic Mass100.01604 Da
IUPAC Name2-oxobut-3-enoic acid
Traditional Name2-oxobut-3-enoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(=O)C=C
InChI Identifier
InChI=1S/C4H4O3/c1-2-3(5)4(6)7/h2H,1H2,(H,6,7)
InChI KeyDGUBLKUCHAAUFT-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
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassKeto acids and derivatives  
Sub ClassShort-chain keto acids and derivatives  
Direct ParentShort-chain keto acids and derivatives  
Alternative Parents
Substituents
  • Short-chain keto acid
    • 

  • Alpha-keto acid
    • 

  • Fatty acyl
    • 

  • Unsaturated fatty acid
    • 

  • Acryloyl-group
    • 

  • Alpha-hydroxy ketone
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Enone
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • 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
logP0.82ChemAxon
pKa (Strongest Acidic)3ChemAxon
pKa (Strongest Basic)-9.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.64 m³·mol⁻¹ChemAxon
Polarizability8.5 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 IDNot Available
Chemspider ID142928  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162804  
PDB IDNot Available
ChEBI ID74021  
Good Scents IDNot Available
References
General References
  1. Liu CH, Wang SA, Ruszczycky MW, Chen H, Li K, Murakami K, Liu HW: Studies of 1-Amino-2,2-difluorocyclopropane-1-carboxylic Acid: Mechanism of Decomposition and Inhibition of 1-Aminocyclopropane-1-carboxylic Acid Deaminase. Org Lett. 2015 Jul 2;17(13):3342-5. doi: 10.1021/acs.orglett.5b01570. Epub 2015  Jun 23. [PubMed:26102233  ] 
  2. Zeinali M, Vossoughi M, Ardestani SK: Degradation of phenanthrene and anthracene by Nocardia otitidiscaviarum strain TSH1, a moderately thermophilic bacterium. J Appl Microbiol. 2008 Aug;105(2):398-406. doi: 10.1111/j.1365-2672.2008.03753.x.  Epub 2008 Feb 29. [PubMed:18312570  ] 
  3. Kim YH, Freeman JP, Moody JD, Engesser KH, Cerniglia CE: Effects of pH on the degradation of phenanthrene and pyrene by Mycobacterium vanbaalenii PYR-1. Appl Microbiol Biotechnol. 2005 Apr;67(2):275-85. doi: 10.1007/s00253-004-1796-y.  Epub 2004 Dec 9. [PubMed:15592827  ] 
  4. LOTUS database [Link]