NP-MRD: Showing NP-Card for 3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl (NP0061105)

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Record Information

Version

2.0

Created at

2022-04-28 06:01:10 UTC

Updated at

2022-04-28 06:01:10 UTC

NP-MRD ID

NP0061105

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl

Description

CHEBI:69421 Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl is found in Polysiphonia stricta and Polysiphonia urceolata. CHEBI:69421 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.7073   -1.5579    1.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9618   -0.5473    0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -0.4699    0.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8317    0.5290    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3623    0.6163    0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167   -0.1433   -0.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547   -0.1247   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4633   -1.1036    0.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8518   -1.1389    0.6288 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878   -2.1004    1.3789 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349   -0.1784    0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0181   -0.2180    0.1690 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0347    0.8091   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0614    2.1466   -1.6189 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.6645    0.8137   -0.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5127    1.4380   -0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8735    1.3653   -0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7617    2.6532   -1.7109 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -4.6258    0.3667   -0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0081    0.2957   -0.2453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3276   -2.2769    1.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792   -1.1948    1.5862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    0.1383    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1073    1.6610    0.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701   -1.1970   -0.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1480    0.2862   -1.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9218   -1.8873    0.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0574   -2.8459    1.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5757    0.4748   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1811    1.5599   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    2.2296   -0.8582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5921   -0.3990    0.1450 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
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  4 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 19  2  1  0
 15  7  1  0
  1 21  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
 10 28  1  0
 12 29  1  0
 15 30  1  0
 16 31  1  0
 20 32  1  0
M  END


  Mrv1533004201501412D          

 20 21  0  0  0  0            999 V2000
    0.0000   -1.6500    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 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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    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
   -1.4289   -4.1250    0.0000 Br  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 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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  7 15  1  0  0  0  0
  4 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061105

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(CCC2=CC(O)=C(O)C(Br)=C2)=CC(Br)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H12Br2O4/c15-9-3-7(5-11(17)13(9)19)1-2-8-4-10(16)14(20)12(18)6-8/h3-6,17-20H,1-2H2

> <INCHI_KEY>
IFYFPCNWTZBOEQ-UHFFFAOYSA-N

> <FORMULA>
C14H12Br2O4

> <MOLECULAR_WEIGHT>
404.054

> <EXACT_MASS>
401.910235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
32.521132459242715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-bromo-5-[2-(3-bromo-4,5-dihydroxyphenyl)ethyl]benzene-1,2-diol

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
4.832852472

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.799838455450676

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.19792580843514

> <JCHEM_PKA_STRONGEST_BASIC>
-6.624418423982996

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
83.5654

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-bromo-5-[2-(3-bromo-4,5-dihydroxyphenyl)ethyl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0       5.335 -13.860   0.000  0.00  0.00          Br+0
HETATM   15  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      -2.667  -7.700   0.000  0.00  0.00          Br+0
HETATM   19  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7                                                       
CONECT   16    4   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₂Br₂O₄

Average Mass

404.0540 Da

Monoisotopic Mass

401.91024 Da

IUPAC Name

3-bromo-5-[2-(3-bromo-4,5-dihydroxyphenyl)ethyl]benzene-1,2-diol

Traditional Name

3-bromo-5-[2-(3-bromo-4,5-dihydroxyphenyl)ethyl]benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

OC1=CC(CCC2=CC(O)=C(O)C(Br)=C2)=CC(Br)=C1O

InChI Identifier

InChI=1S/C14H12Br2O4/c15-9-3-7(5-11(17)13(9)19)1-2-8-4-10(16)14(20)12(18)6-8/h3-6,17-20H,1-2H2

InChI Key

IFYFPCNWTZBOEQ-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Polysiphonia stricta	LOTUS Database	35616633
Polysiphonia urceolata	--	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Catechol
3-halophenol
2-halophenol
3-bromophenol
2-bromophenol
Phenol
Bromobenzene
Halobenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Aryl halide
Aryl bromide
Benzenoid
Organooxygen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

stilbenoid (CHEBI:69421 )

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	3.59	ALOGPS
logP	4.83	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.2	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.57 m³·mol⁻¹	ChemAxon
Polarizability	32.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

44437166

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl (NP0061105)

MOL for NP0061105 (3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl)

3D MOL for NP0061105 (3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl)

3D SDF for NP0061105 (3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl)

3D-SDF for NP0061105 (3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl)

PDB for NP0061105 (3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl)

3D PDB for NP0061105 (3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl)

SMILES for NP0061105 (3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl)

INCHI for NP0061105 (3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl)

Structure for NP0061105 (3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl)

3D Structure for NP0061105 (3,3'-Dibromo-4,4',5,5'-tetrahydroxybibenzyl)