NP-MRD: Showing NP-Card for 7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol (NP0239443)

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Record Information

Version

2.0

Created at

2022-09-06 23:02:47 UTC

Updated at

2022-09-06 23:02:47 UTC

NP-MRD ID

NP0239443

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol

Description

(+)-3-(2,3-Dibromo-4,5-dihydroxyphenyl)-4-bromo-5,6-dihydroxy-1,3-dihydroisobenzofuran belongs to the class of organic compounds known as isocoumarans. Isocoumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring (+)-3-(2,3-dibromo-4,5-dihydroxyphenyl)-4-bromo-5,6-dihydroxy-1,3-dihydroisobenzofuran is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    4.2856   -1.0055    1.8046 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399   -0.4354    0.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316   -1.0503    0.6180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3258   -0.5588   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550   -1.2448   -0.5279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2639   -1.3886   -1.8797 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5904   -1.8576   -1.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749   -0.8803   -0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4054   -0.3255   -0.5856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6504    0.5909    0.4029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8959    1.1516    0.6503 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5949    0.9789    1.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7610    1.9005    2.2201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3249    0.4334    0.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1470    0.9555    2.0670 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1251   -0.4820   -0.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6479    0.5902   -0.9713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635    1.3549   -2.2550 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.8518    1.2136   -0.7280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3430    2.8158   -1.6492 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.7567    0.7185    0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9552    1.3311    0.4329 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1774   -0.6425    2.0597 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876   -1.9466    1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0554   -2.2805   -0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5809   -2.8850   -1.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0328   -1.7524   -2.8027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2222   -0.6279   -1.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6848    0.8686    0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6848    2.2820    2.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2690    2.1782   -0.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8 16  2  0
 16  5  1  0
  5  6  1  0
  6  7  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  2 21  2  0
 21 22  1  0
 21 19  1  0
 19 20  1  0
 19 17  2  0
 17 18  1  0
 16 14  1  0
 14 15  1  0
 14 12  2  0
 12 13  1  0
 12 10  1  0
  7  8  1  0
 17  4  1  0
 11 29  1  0
  9 28  1  0
  5 25  1  1
  7 26  1  0
  7 27  1  0
  3 24  1  0
  1 23  1  0
 22 31  1  0
 13 30  1  0
M  END


  Mrv1533004241503272D          

 22 24  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    3.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673    4.1027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083    4.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633    5.3289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1014    4.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4507    4.9858    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.1536    3.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9606    3.4166    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    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  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
  7 18  1  0  0  0  0
  4 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0239443

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C(OC2)C2=CC(O)=C(O)C(Br)=C2Br)C(Br)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H9Br3O5/c15-9-5(2-7(19)13(21)11(9)17)14-8-4(3-22-14)1-6(18)12(20)10(8)16/h1-2,14,18-21H,3H2

> <INCHI_KEY>
VPLSCECMILOJAG-UHFFFAOYSA-N

> <FORMULA>
C14H9Br3O5

> <MOLECULAR_WEIGHT>
496.933

> <EXACT_MASS>
493.800012

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
34.606877989655295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol

> <ALOGPS_LOGP>
4.25

> <JCHEM_LOGP>
4.4764866303333335

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.108785218837435

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.382665445389822

> <JCHEM_PKA_STRONGEST_BASIC>
-4.240381758267791

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
91.2545

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       5.198   1.303   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.173   2.843   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.744   5.553   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.250   5.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.726   7.338   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.232   7.658   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.696   8.483   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.171   9.947   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.189   8.162   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0       0.841   9.307   0.000  0.00  0.00          Br+0
HETATM   16  C   UNK     0       0.287   6.698   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0       1.793   6.378   0.000  0.00  0.00          Br+0
HETATM   18  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   20 Br   UNK     0       2.530   5.923   0.000  0.00  0.00          Br+0
HETATM   21  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16                                                            
CONECT   18    7    4   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    2   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₉Br₃O₅

Average Mass

496.9330 Da

Monoisotopic Mass

493.80001 Da

IUPAC Name

7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol

Traditional Name

7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C(OC2)C2=CC(O)=C(O)C(Br)=C2Br)C(Br)=C1O

InChI Identifier

InChI=1S/C14H9Br3O5/c15-9-5(2-7(19)13(21)11(9)17)14-8-4(3-22-14)1-6(18)12(20)10(8)16/h1-2,14,18-21H,3H2

InChI Key

VPLSCECMILOJAG-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 isocoumarans. Isocoumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 1,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Not Available

Direct Parent

Isocoumarans

Alternative Parents

Substituents

Isocoumaran
Catechol
4-halophenol
3-halophenol
2-halophenol
3-bromophenol
2-bromophenol
4-bromophenol
Bromobenzene
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Phenol
Benzenoid
Aryl halide
Aryl bromide
Monocyclic benzene moiety
Oxacycle
Ether
Dialkyl ether
Hydrocarbon derivative
Organic oxygen compound
Organohalogen compound
Organobromide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.25	ALOGPS
logP	4.48	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	7.38	ChemAxon
pKa (Strongest Basic)	-4.2	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	1	ChemAxon
Refractivity	91.25 m³·mol⁻¹	ChemAxon
Polarizability	34.61 Å³	ChemAxon
Number of Rings	3	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

11340945

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol (NP0239443)

MOL for NP0239443 (7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol)

3D MOL for NP0239443 (7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol)

3D SDF for NP0239443 (7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol)

3D-SDF for NP0239443 (7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol)

PDB for NP0239443 (7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol)

3D PDB for NP0239443 (7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol)

SMILES for NP0239443 (7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol)

INCHI for NP0239443 (7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol)

Structure for NP0239443 (7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol)

3D Structure for NP0239443 (7-bromo-1-(2,3-dibromo-4,5-dihydroxyphenyl)-1,3-dihydro-2-benzofuran-5,6-diol)