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Showing NP-Card for 2-Chloromaleylacetate (NP0054984)

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Record Information
Version2.0
Created at2022-04-28 01:10:14 UTC
Updated at2022-04-28 01:10:14 UTC
NP-MRD IDNP0054984
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Chloromaleylacetate
Description2-Chloromaleylacetate 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. 2-Chloromaleylacetate is found in Escherichia coli and Sphingobium chlorophenolicum. 2-Chloromaleylacetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0054984 (2-Chloromaleylacetate)

 
  Mrv0541 07191211052D          
 
 12 11  0  0  0  0            999 V2000
   16.6349  -10.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9177  -10.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3488  -10.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6349  -11.6160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9177   -9.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0593  -10.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6349   -9.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2039   -9.1381    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.7697  -10.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0626  -11.6023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6349   -8.3144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3453   -9.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  1  0  0  0  0
  7 12  2  0  0  0  0
M  END
Download

3D MOL for NP0054984 (2-Chloromaleylacetate)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.4058    1.4006   -1.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2217    0.6505   -0.5945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5681    0.9010   -0.6180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7067   -0.5336    0.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1881   -0.5716    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -1.5363   -0.6567 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5509    0.4837    0.6055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8538    0.6107    0.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036    2.0558    1.4051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7434   -0.2694   -0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9809    0.0647   -0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4534   -1.3946   -0.7930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1727    0.6259    0.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9987   -0.4441    1.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1639   -1.4262   -0.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0363    1.2711    1.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551   -1.8881   -1.3649 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 12  1  0
 10 11  2  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  7 16  1  0
 12 17  1  0
M  END
Download

3D SDF for NP0054984 (2-Chloromaleylacetate)

 
  Mrv0541 07191211052D          
 
 12 11  0  0  0  0            999 V2000
   16.6349  -10.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9177  -10.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3488  -10.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6349  -11.6160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9177   -9.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0593  -10.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6349   -9.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2039   -9.1381    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.7697  -10.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0626  -11.6023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6349   -8.3144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3453   -9.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  1  0  0  0  0
  7 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0054984

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H5ClO5/c7-4(6(11)12)1-3(8)2-5(9)10/h1H,2H2,(H,9,10)(H,11,12)/b4-1+

> <INCHI_KEY>
QOHGUQUQCPIROQ-DAFODLJHSA-N

> <FORMULA>
C6H5ClO5

> <MOLECULAR_WEIGHT>
192.554

> <EXACT_MASS>
191.982550977

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
15.26284616248616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-2-chloro-4-oxohex-2-enedioic acid

> <ALOGPS_LOGP>
0.30

> <JCHEM_LOGP>
0.569891954

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.563734546273973

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.014240532206885

> <JCHEM_PKA_STRONGEST_BASIC>
-7.987452639501679

> <JCHEM_POLAR_SURFACE_AREA>
91.66999999999999

> <JCHEM_REFRACTIVITY>
39.2935

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.85e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-chloromaleylacetate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0054984 (2-Chloromaleylacetate)

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PDB for NP0054984 (2-Chloromaleylacetate)
HEADER    PROTEIN                                 19-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-12         0                                  
HETATM    1  C   UNK     0      31.052 -20.139   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.713 -19.364   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      32.384 -19.364   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      31.052 -21.683   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      29.713 -17.827   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.711 -20.126   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.052 -17.058   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0      28.381 -17.058   0.000  0.00  0.00          Cl+0
HETATM    9  O   UNK     0      35.037 -19.358   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      33.717 -21.658   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      31.052 -15.520   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      32.378 -17.827   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1                                                            
CONECT    5    2    7    8                                                  
CONECT    6    3    9   10                                                  
CONECT    7    5   11   12                                                  
CONECT    8    5                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0054984 (2-Chloromaleylacetate)
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SMILES for NP0054984 (2-Chloromaleylacetate)
OC(=O)CC(=O)\C=C(\Cl)C(O)=O
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INCHI for NP0054984 (2-Chloromaleylacetate)
InChI=1S/C6H5ClO5/c7-4(6(11)12)1-3(8)2-5(9)10/h1H,2H2,(H,9,10)(H,11,12)/b4-1+
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Synonyms
ValueSource
2-Chloromaleylacetic acidGenerator
2-Chloromaleylacetate, (e)-isomerHMDB
2-Chloro-4-oxo-(Z)-2-hexenedioic acidHMDB
(2E)-2-Chloro-4-oxohex-2-enedioateGenerator
Chemical FormulaC6H5ClO5
Average Mass192.5540 Da
Monoisotopic Mass191.98255 Da
IUPAC Name(2E)-2-chloro-4-oxohex-2-enedioic acid
Traditional Name2-chloromaleylacetate
CAS Registry NumberNot Available
SMILES
OC(=O)CC(=O)\C=C(\Cl)C(O)=O
InChI Identifier
InChI=1S/C6H5ClO5/c7-4(6(11)12)1-3(8)2-5(9)10/h1H,2H2,(H,9,10)(H,11,12)/b4-1+
InChI KeyQOHGUQUQCPIROQ-DAFODLJHSA-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
Escherichia coliBacteria
Sphingobium chlorophenolicumBacteria
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
    • 

  • Beta-keto acid
    • 

  • B'-hydroxy-alpha,beta-unsaturated-ketone
    • 

  • Halogenated fatty acid
    • 

  • Fatty acyl
    • 

  • Beta-hydroxy ketone
    • 

  • 1,3-dicarbonyl compound
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Unsaturated fatty acid
    • 

  • Acryloyl-group
    • 

  • Alpha-halocarboxylic acid
    • 

  • Alpha-halocarboxylic acid or derivatives
    • 

  • Vinylogous halide
    • 

  • Alpha,beta-unsaturated ketone
    • 

  • Enone
    • 

  • Ketone
    • 

  • Chloroalkene
    • 

  • Haloalkene
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Vinyl halide
    • 

  • Vinyl chloride
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organochloride
    • 

  • Organohalogen 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
logP0.3ALOGPS
logP0.57ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.01ChemAxon
pKa (Strongest Basic)-8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity39.29 m³·mol⁻¹ChemAxon
Polarizability15.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0060347  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00007488  
Chemspider IDNot Available
KEGG Compound IDC06329  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9776838  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References