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Showing NP-Card for [(2r)-2-chloro-5-oxofuran-2-yl]acetic acid (NP0314791)

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Record Information
Version1.0
Created at2022-09-11 13:05:14 UTC
Updated at2022-09-11 13:05:15 UTC
NP-MRD IDNP0314791
Secondary Accession NumbersNone
Natural Product Identification
Common Name[(2r)-2-chloro-5-oxofuran-2-yl]acetic acid
Description(R)-(2-chloro-5-oxo-2,5-dihydro-2-furyl)acetic acid belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom (R)-(2-chloro-5-oxo-2,5-dihydro-2-furyl)acetic 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. It was first documented in 2003 (PMID: 12930985). Based on a literature review very few articles have been published on (R)-(2-chloro-5-oxo-2,5-dihydro-2-furyl)acetic acid.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0314791 ([(2r)-2-chloro-5-oxofuran-2-yl]acetic acid)


  Mrv1652309112215052D          

 11 11  0  0  1  0            999 V2000
    1.4169    3.1251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579    2.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    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  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
M  END
Download

3D MOL for NP0314791 ([(2r)-2-chloro-5-oxofuran-2-yl]acetic acid)

     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
    2.3677   -0.2329    0.9666 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -0.0852   -0.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8256    0.7443   -1.0264 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8894   -0.7569   -0.8043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3938   -0.5004   -0.0363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2254   -1.0581    1.6455 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7953    0.8817   -0.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9838    1.0083   -0.5403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4462   -0.3098   -0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5730   -0.5724   -1.4772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4597   -1.2112   -0.6145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8376    0.7800   -1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7026   -0.4517   -1.8604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0045   -1.8752   -0.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112    1.7249    0.3571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855    1.9145   -0.6866 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  1  1
  5 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  2  0
  7  5  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  8 16  1  0
  7 15  1  0
M  END
Download

3D SDF for NP0314791 ([(2r)-2-chloro-5-oxofuran-2-yl]acetic acid)


  Mrv1652309112215052D          

 11 11  0  0  1  0            999 V2000
    1.4169    3.1251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8649    2.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579    2.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    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  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  5 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C[C@]1(Cl)OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H5ClO4/c7-6(3-4(8)9)2-1-5(10)11-6/h1-2H,3H2,(H,8,9)/t6-/m1/s1

> <INCHI_KEY>
WGZZDRVKIXVYEI-ZCFIWIBFSA-N

> <FORMULA>
C6H5ClO4

> <MOLECULAR_WEIGHT>
176.55

> <EXACT_MASS>
175.9876363

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
14.273313479029671

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2R)-2-chloro-5-oxo-2,5-dihydrofuran-2-yl]acetic acid

> <JCHEM_LOGP>
1.315452692

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5185753614238933

> <JCHEM_PKA_STRONGEST_BASIC>
-6.871036754005882

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
36.706500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2R)-2-chloro-5-oxofuran-2-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0314791 ([(2r)-2-chloro-5-oxofuran-2-yl]acetic acid)

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PDB for NP0314791 ([(2r)-2-chloro-5-oxofuran-2-yl]acetic acid)
HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0       2.645   5.834   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.614   4.689   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.108   5.009   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       0.029   3.224   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.615  -1.536   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0314791 ([(2r)-2-chloro-5-oxofuran-2-yl]acetic acid)
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SMILES for NP0314791 ([(2r)-2-chloro-5-oxofuran-2-yl]acetic acid)
OC(=O)C[C@]1(Cl)OC(=O)C=C1
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INCHI for NP0314791 ([(2r)-2-chloro-5-oxofuran-2-yl]acetic acid)
InChI=1S/C6H5ClO4/c7-6(3-4(8)9)2-1-5(10)11-6/h1-2H,3H2,(H,8,9)/t6-/m1/s1
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View in JSmol
Synonyms
ValueSource
(+)-4-ChloromuconolactoneChEBI
(R)-(2-Chloro-5-oxo-2,5-dihydro-2-furyl)acetateGenerator
Chemical FormulaC6H5ClO4
Average Mass176.5500 Da
Monoisotopic Mass175.98764 Da
IUPAC Name2-[(2R)-2-chloro-5-oxo-2,5-dihydrofuran-2-yl]acetic acid
Traditional Name[(2R)-2-chloro-5-oxofuran-2-yl]acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C[C@]1(Cl)OC(=O)C=C1
InChI Identifier
InChI=1S/C6H5ClO4/c7-6(3-4(8)9)2-1-5(10)11-6/h1-2H,3H2,(H,8,9)/t6-/m1/s1
InChI KeyWGZZDRVKIXVYEI-ZCFIWIBFSA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDihydrofurans  
Sub ClassFuranones  
Direct ParentButenolides  
Alternative Parents
Substituents
  • 2-furanone
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organooxygen compound
    • 

  • Organochloride
    • 

  • Organohalogen compound
    • 

  • Alkyl chloride
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Alkyl halide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • (2-chloro-5-oxo-2,5-dihydro-2-furyl)acetic acid (CHEBI:85800  )
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
logP1.32ChemAxon
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity36.71 m³·mol⁻¹ChemAxon
Polarizability14.27 ųChemAxon
Number of Rings1ChemAxon
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 ID34999811  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25244291  
PDB IDNot Available
ChEBI ID85800  
Good Scents IDNot Available
References
General References
  1. Kajander T, Lehtio L, Schlomann M, Goldman A: The structure of Pseudomonas P51 Cl-muconate lactonizing enzyme: co-evolution of structure and dynamics with the dehalogenation function. Protein Sci. 2003 Sep;12(9):1855-64. doi: 10.1110/ps.0388503. [PubMed:12930985  ] 
  2. LOTUS database [Link]