NP-MRD: Showing NP-Card for 3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol (NP0329501)

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Record Information

Version

2.0

Created at

2022-09-12 13:56:52 UTC

Updated at

2022-09-12 13:56:53 UTC

NP-MRD ID

NP0329501

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol

Description

1,1-Dichloro-2-(4-chloro-2,3-dihydroxyphenyl)-2-(4-chlorophenyl)ethylene, also known as 3-[2,2-dichloro-1-(4-chlorophenyl)vinyl]-6-chlorobenzene-1,2-diol or 2,3-dihydroxy-dde, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. 1,1-Dichloro-2-(4-chloro-2,3-dihydroxyphenyl)-2-(4-chlorophenyl)ethylene is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol is found in Apis cerana. Based on a literature review very few articles have been published on 1,1-dichloro-2-(4-chloro-2,3-dihydroxyphenyl)-2-(4-chlorophenyl)ethylene.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
    3.8935    0.0018    2.0363 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0399    0.2778    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3255    1.2881    0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7894    2.2234    0.3364 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4513    1.5172   -0.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3019    0.7287   -1.0873 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0420   -0.2754   -0.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2020   -1.1124   -0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0125   -2.3789   -0.5398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2029   -3.6139   -0.7285 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6885   -2.9716   -0.7723 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392   -0.3951   -0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6787   -0.9206   -0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8722   -0.1766   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7636    1.1151    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2232    2.0701    0.3428 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5460    1.7109    0.4047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4305    0.9456    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9007   -0.5190    0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6518   -1.5186    1.7884 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6834   -0.7364    2.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6966    2.3008   -1.6315 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6322    0.9227   -1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782   -1.9272   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8168   -0.6869   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918    2.7413    0.7239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4760    1.4413    0.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8118   -2.0523    1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  8 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
  7 19  2  0
 19 20  1  0
 19  2  1  0
 18 12  1  0
  1 21  1  0
  5 22  1  0
  6 23  1  0
 13 24  1  0
 14 25  1  0
 17 26  1  0
 18 27  1  0
 20 28  1  0
M  END


  Mrv1652309122215562D          

 20 21  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
  7 19  2  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329501

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(Cl)C=CC(C(=C(Cl)Cl)C2=CC=C(Cl)C=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H8Cl4O2/c15-8-3-1-7(2-4-8)11(14(17)18)9-5-6-10(16)13(20)12(9)19/h1-6,19-20H

> <INCHI_KEY>
FLLUEFJGXSALFO-UHFFFAOYSA-N

> <FORMULA>
C14H8Cl4O2

> <MOLECULAR_WEIGHT>
350.02

> <EXACT_MASS>
347.9278403

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
31.518119366218343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol

> <JCHEM_LOGP>
5.498433557333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.275932321437821

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.845179010245639

> <JCHEM_PKA_STRONGEST_BASIC>
-6.757888941892149

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
103.26799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       6.668  -2.310   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0      -0.000  -7.700   0.000  0.00  0.00          Cl+0
HETATM   11 Cl   UNK     0       2.667  -7.700   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      -4.001  -2.310   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
CONECT   19    7    2   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
1,1-Dichloro-2-(dihydroxy-4'-chlorophenyl)-2-(4'-chlorophenyl)ethylene	ChEBI
3-[2,2-Dichloro-1-(4-chlorophenyl)vinyl]-6-chlorobenzene-1,2-diol	Kegg
2,3-Dihydroxy-dde	Kegg

Chemical Formula

C₁₄H₈Cl₄O₂

Average Mass

350.0200 Da

Monoisotopic Mass

347.92784 Da

IUPAC Name

3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol

Traditional Name

3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

OC1=C(Cl)C=CC(C(=C(Cl)Cl)C2=CC=C(Cl)C=C2)=C1O

InChI Identifier

InChI=1S/C14H8Cl4O2/c15-8-3-1-7(2-4-8)11(14(17)18)9-5-6-10(16)13(20)12(9)19/h1-6,19-20H

InChI Key

FLLUEFJGXSALFO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
3-chlorocatechol
Chlorocatechol
Catechol
3-halophenol
2-halophenol
3-chlorophenol
2-chlorophenol
Phenol
Chlorobenzene
Halobenzene
1-hydroxy-4-unsubstituted benzenoid
Aryl halide
Aryl chloride
Ketene acetal or derivatives
Vinyl halide
Haloalkene
Chloroalkene
Vinyl chloride
Hydrocarbon derivative
Organic oxygen compound
Organohalogen compound
Organochloride
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:28959 )
monochlorobenzenes (CHEBI:28959 )
chlorophenylethylene (CHEBI:28959 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.5	ChemAxon
pKa (Strongest Acidic)	7.85	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.27 m³·mol⁻¹	ChemAxon
Polarizability	31.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

389912

KEGG Compound ID

C06644

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441114

PDB ID

Not Available

ChEBI ID

28959

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol (NP0329501)

MOL for NP0329501 (3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol)

3D MOL for NP0329501 (3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol)

3D SDF for NP0329501 (3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol)

3D-SDF for NP0329501 (3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol)

PDB for NP0329501 (3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol)

3D PDB for NP0329501 (3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol)

SMILES for NP0329501 (3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol)

INCHI for NP0329501 (3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol)

Structure for NP0329501 (3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol)

3D Structure for NP0329501 (3-chloro-6-[2,2-dichloro-1-(4-chlorophenyl)ethenyl]benzene-1,2-diol)