NP-MRD: Showing NP-Card for 3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol (NP0303206)

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Record Information

Version

2.0

Created at

2022-09-10 17:22:31 UTC

Updated at

2022-09-10 17:22:31 UTC

NP-MRD ID

NP0303206

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol

Description

3,4-Dibromo-5-[(2-bromo-3,4-dihydroxy-6-methoxyphenyl)methyl]benzene-1,2-diol 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. 3,4-Dibromo-5-[(2-bromo-3,4-dihydroxy-6-methoxyphenyl)methyl]benzene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.6274   -1.1859    2.7570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1284   -1.1479    1.4699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6134   -0.4274    0.4074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458    0.3846    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2725    1.1287   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858    1.9014   -0.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7013    1.1006   -1.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2433    1.8555   -2.7442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6000    0.3119   -1.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8161    0.2091   -3.6165 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434   -0.4595   -0.8286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -1.2898   -1.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139   -0.8668   -0.5619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0331    0.2589   -1.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1714    0.7758   -0.5620 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7510    1.8904   -1.1498 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7726    0.2485    0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9244    0.8050    1.0922 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1779   -0.8535    1.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9673   -1.6229    2.6594 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.0174   -1.3988    0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3925   -3.0059    1.3182 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7304   -1.3602    2.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1151   -2.0383    3.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4065   -0.2836    3.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831    0.3890    1.5796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8669    2.4820   -0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0483    2.4402   -2.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721   -2.3683   -0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592   -1.3305   -2.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6395    0.7336   -1.9927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5892    2.3180   -0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3524    0.4064    1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 11  3  1  0
 21 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  8 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 16 32  1  0
 18 33  1  0
M  END


  Mrv1533004191520132D          

 22 23  0  0  0  0            999 V2000
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   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
   -1.4289   -1.6500    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
   -2.1434   -2.8875    0.0000 O   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 O   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 Br  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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303206

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(O)C(Br)=C1CC1=CC(O)=C(O)C(Br)=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C14H11Br3O5/c1-22-9-4-8(19)13(20)11(16)6(9)2-5-3-7(18)14(21)12(17)10(5)15/h3-4,18-21H,2H2,1H3

> <INCHI_KEY>
WFSYQFGCTUZIIG-UHFFFAOYSA-N

> <FORMULA>
C14H11Br3O5

> <MOLECULAR_WEIGHT>
498.949

> <EXACT_MASS>
495.815662

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
35.80003359680801

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol

> <ALOGPS_LOGP>
4.80

> <JCHEM_LOGP>
4.999365166666666

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.69711439874644

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.691808155498328

> <JCHEM_PKA_STRONGEST_BASIC>
-4.83086492765947

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
93.05040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10 Br   UNK     0       1.334  -5.390   0.000  0.00  0.00          Br+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20 Br   UNK     0       4.001   2.310   0.000  0.00  0.00          Br+0
HETATM   21  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   22 Br   UNK     0       4.001  -0.770   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    3   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   13   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₁Br₃O₅

Average Mass

498.9490 Da

Monoisotopic Mass

495.81566 Da

IUPAC Name

3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol

Traditional Name

3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(O)C(Br)=C1CC1=CC(O)=C(O)C(Br)=C1Br

InChI Identifier

InChI=1S/C14H11Br3O5/c1-22-9-4-8(19)13(20)11(16)6(9)2-5-3-7(18)14(21)12(17)10(5)15/h3-4,18-21H,2H2,1H3

InChI Key

WFSYQFGCTUZIIG-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

Not Available

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
Methoxyphenol
4-alkoxyphenol
Anisole
Catechol
Phenoxy compound
4-halophenol
3-halophenol
2-halophenol
3-bromophenol
2-bromophenol
4-bromophenol
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Bromobenzene
Alkyl aryl ether
Halobenzene
Phenol
Aryl halide
Aryl bromide
Ether
Organohalogen compound
Organobromide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	4.8	ALOGPS
logP	5	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.69	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.05 m³·mol⁻¹	ChemAxon
Polarizability	35.8 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102580524

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol (NP0303206)

MOL for NP0303206 (3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol)

3D MOL for NP0303206 (3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol)

3D SDF for NP0303206 (3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol)

3D-SDF for NP0303206 (3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol)

PDB for NP0303206 (3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol)

3D PDB for NP0303206 (3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol)

SMILES for NP0303206 (3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol)

INCHI for NP0303206 (3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol)

Structure for NP0303206 (3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol)

3D Structure for NP0303206 (3-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-methoxybenzene-1,2-diol)