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Showing NP-Card for (5r)-3,4-dichloro-5-hydroxy-5h-furan-2-one (NP0229714)

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Record Information
Version2.0
Created at2022-09-06 09:53:46 UTC
Updated at2022-09-06 09:53:46 UTC
NP-MRD IDNP0229714
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5r)-3,4-dichloro-5-hydroxy-5h-furan-2-one
DescriptionZINC3882174 belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. (5r)-3,4-dichloro-5-hydroxy-5h-furan-2-one is found in Lessingianthus linearis. Based on a literature review very few articles have been published on ZINC3882174.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0229714 ((5r)-3,4-dichloro-5-hydroxy-5h-furan-2-one)


  Mrv1652309062211532D          

  9  9  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 O   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
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   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 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 Cl  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  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
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3D MOL for NP0229714 ((5r)-3,4-dichloro-5-hydroxy-5h-furan-2-one)

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3D SDF for NP0229714 ((5r)-3,4-dichloro-5-hydroxy-5h-furan-2-one)

  Mrv1652309062211532D          

  9  9  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 O   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
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   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 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 Cl  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  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0229714

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1OC(=O)C(Cl)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C4H2Cl2O3/c5-1-2(6)4(8)9-3(1)7/h3,7H/t3-/m1/s1

> <INCHI_KEY>
ZAKLKBFCSHJIRI-GSVOUGTGSA-N

> <FORMULA>
C4H2Cl2O3

> <MOLECULAR_WEIGHT>
168.96

> <EXACT_MASS>
167.9380993

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
12.51967658745799

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R)-3,4-dichloro-5-hydroxy-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
0.7981070626666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.987698012838486

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.5612521196458

> <JCHEM_PKA_STRONGEST_BASIC>
-4.692492904517686

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
31.784800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-3,4-dichloro-5-hydroxy-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0229714 ((5r)-3,4-dichloro-5-hydroxy-5h-furan-2-one)
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PDB for NP0229714 ((5r)-3,4-dichloro-5-hydroxy-5h-furan-2-one)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    7 Cl   UNK     0      -0.615  -1.536   0.000  0.00  0.00          Cl+0
HETATM    8  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0      -1.651   1.651   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0229714 ((5r)-3,4-dichloro-5-hydroxy-5h-furan-2-one)
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SMILES for NP0229714 ((5r)-3,4-dichloro-5-hydroxy-5h-furan-2-one)
O[C@@H]1OC(=O)C(Cl)=C1Cl
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INCHI for NP0229714 ((5r)-3,4-dichloro-5-hydroxy-5h-furan-2-one)
InChI=1S/C4H2Cl2O3/c5-1-2(6)4(8)9-3(1)7/h3,7H/t3-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC4H2Cl2O3
Average Mass168.9600 Da
Monoisotopic Mass167.93810 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
O[C@@H]1OC(=O)C(Cl)=C1Cl
InChI Identifier
InChI=1S/C4H2Cl2O3/c5-1-2(6)4(8)9-3(1)7/h3,7H/t3-/m1/s1
InChI KeyZAKLKBFCSHJIRI-GSVOUGTGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lessingianthus linearisLOTUS Database
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
    • 

  • Vinylogous halide
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Chlorohydrin
    • 

  • Halohydrin
    • 

  • Hemiacetal
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Chloroalkene
    • 

  • Haloalkene
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Vinyl chloride
    • 

  • Vinyl halide
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organohalogen compound
    • 

  • Organochloride
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4483402  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5325919  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]