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Showing NP-Card for 2-chloro-trans-dienelactone (NP0334309)

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Record Information
Version2.0
Created at2024-09-09 23:06:11 UTC
Updated at2024-09-09 23:06:11 UTC
NP-MRD IDNP0334309
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-chloro-trans-dienelactone
Description2-Chloro-trans-dienelactone, also known as cis-2-chloro-4-carboxymethylenebut-2-en-1,4-olide, is a member of the class of compounds known as butenolides. Butenolides are dihydrofurans with a carbonyl group at the C2 carbon atom. 2-Chloro-trans-dienelactone is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 2-Chloro-trans-dienelactone can be found in a number of food items such as giant butterbur, soy bean, common persimmon, and salmonberry, which makes 2-chloro-trans-dienelactone a potential biomarker for the consumption of these food products.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334309 (2-chloro-trans-dienelactone)


  Mrv1533007131514082D          

 12 12  0  0  0  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    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
   -0.1467    2.3518    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
    1.4652   -0.8227    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 O   0  5  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
    1.2822    2.3518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  2  1  0  0  0  0
M  CHG  1   9  -1
M  END
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3D MOL for NP0334309 (2-chloro-trans-dienelactone)

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3D SDF for NP0334309 (2-chloro-trans-dienelactone)

  Mrv1533007131514082D          

 12 12  0  0  0  0            999 V2000
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    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
   -0.1467    2.3518    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
    1.4652   -0.8227    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 O   0  5  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
    1.2822    2.3518    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  2  1  0  0  0  0
M  CHG  1   9  -1
M  END
> <DATABASE_ID>
NP0334309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C([O-])=O)=C1\OC(=O)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H3ClO4/c7-4-1-3(2-5(8)9)11-6(4)10/h1-2H,(H,8,9)/p-1/b3-2-

> <INCHI_KEY>
ADSGHWJRPOXXTD-IHWYPQMZSA-M

> <FORMULA>
C6H2ClO4

> <MOLECULAR_WEIGHT>
173.53

> <EXACT_MASS>
172.9647098

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
13.739491995982428

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2Z)-4-chloro-5-oxo-2,5-dihydrofuran-2-ylidene]acetate

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
0.5719121033333332

> <ALOGPS_LOGS>
-1.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6842205271850617

> <JCHEM_PKA_STRONGEST_BASIC>
-7.334826519314273

> <JCHEM_POLAR_SURFACE_AREA>
66.42999999999999

> <JCHEM_REFRACTIVITY>
48.954100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2Z)-4-chloro-5-oxofuran-2-ylidene]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334309 (2-chloro-trans-dienelactone)
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PDB for NP0334309 (2-chloro-trans-dienelactone)
HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0       2.735  -1.536   0.000  0.00  0.00          Cl+0
HETATM    8  O   UNK     0      -1.608   3.620   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.274   5.930   0.000  0.00  0.00           O-1
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
HETATM   12  H   UNK     0       2.393   4.390   0.000  0.00  0.00           H+0
CONECT    1    3    4                                                       
CONECT    2    3    5   12                                                  
CONECT    3    1    2   11                                                  
CONECT    4    1    6    7                                                  
CONECT    5    2    8    9                                                  
CONECT    6    4   10   11                                                  
CONECT    7    4                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    3    6                                                       
CONECT   12    2                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0334309 (2-chloro-trans-dienelactone)
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SMILES for NP0334309 (2-chloro-trans-dienelactone)
[H]\C(C([O-])=O)=C1\OC(=O)C(Cl)=C1
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INCHI for NP0334309 (2-chloro-trans-dienelactone)
InChI=1S/C6H3ClO4/c7-4-1-3(2-5(8)9)11-6(4)10/h1-2H,(H,8,9)/p-1/b3-2-
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Synonyms
ValueSource
trans-2-Chloro-4-carboxylatomethylenebut-2-en-1,4-olideChEBI
trans-2-Chloro-4-carboxylatomethylenebut-2-en-1,4-olide anionChEBI
trans-2-Chloro-4-carboxymethylenebut-2-en-1,4-olideChEBI
Chemical FormulaC6H2ClO4
Average Mass173.5300 Da
Monoisotopic Mass172.96471 Da
IUPAC Name2-[(2Z)-4-chloro-5-oxo-2,5-dihydrofuran-2-ylidene]acetate
Traditional Name2-[(2Z)-4-chloro-5-oxofuran-2-ylidene]acetate
CAS Registry NumberNot Available
SMILES
[H]\C(C([O-])=O)=C1\OC(=O)C(Cl)=C1
InChI Identifier
InChI=1S/C6H3ClO4/c7-4-1-3(2-5(8)9)11-6(4)10/h1-2H,(H,8,9)/p-1/b3-2-
InChI KeyADSGHWJRPOXXTD-IHWYPQMZSA-M
Experimental Spectra
Not Available
Predicted Spectra
Not Available
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
    • 

  • Enol ester
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Oxacycle
    • 

  • Chloroalkene
    • 

  • Vinyl chloride
    • 

  • Vinyl halide
    • 

  • Haloalkene
    • 

  • Carbonyl group
    • 

  • Organohalogen compound
    • 

  • Organochloride
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic anion
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP1.05ALOGPS
logP0.57ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.68ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area66.43 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.95 m³·mol⁻¹ChemAxon
Polarizability13.74 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 IDFDB030329  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543229  
PDB IDNot Available
ChEBI ID57891  
Good Scents IDNot Available
References
General ReferencesNot Available