NP-MRD: Showing NP-Card for 3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid (NP0301071)

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Record Information

Version

2.0

Created at

2022-09-10 13:48:50 UTC

Updated at

2022-09-10 13:48:51 UTC

NP-MRD ID

NP0301071

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid

Description

3-(2,3-Dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid 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-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid is found in Rhodomela confervoides. 3-(2,3-Dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid 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
   -1.3448   -1.0983    1.9580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4531   -0.4413    1.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386   -0.5469    1.8921 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7955    0.3970    0.2280 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0069   -0.0782   -0.9800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4645    0.0232   -0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348   -1.1039   -0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5876   -1.0005   -0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3352   -2.1340    0.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279    0.2207   -0.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5746    0.3064    0.0084 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974    1.3445   -0.5119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3348    3.0775   -0.5786 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    1.2227   -0.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1566    2.8015   -1.1347 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2509    0.2823   -0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8306   -0.9403   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1797   -1.0637   -0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0191    0.0259   -0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4579    1.2474   -0.2375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1065    1.3725    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1272   -1.4038    2.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5778    1.4770    0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2894   -1.1226   -1.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3309    0.5382   -1.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7707   -2.0745   -0.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9197   -3.0647    0.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0502    1.1879   -0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1706   -1.7979   -0.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6092   -2.0263   -0.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1001   -0.0734   -0.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1115    2.1156   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409    2.3300    0.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
  4 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 14  6  1  0
 21 16  1  0
  3 22  1  0
  4 23  1  1
  5 24  1  0
  5 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
 20 32  1  0
 21 33  1  0
M  END


  Mrv1533004191520222D          

 21 22  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 O   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
    0.0000   -2.4750    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
    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 O   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 Br  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
    2.8579   -2.4750    0.0000 Br  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 C   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
    1.4289    0.0000    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0301071

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(CC1=CC(O)=C(O)C(Br)=C1Br)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H12Br2O4/c16-12-9(7-11(18)14(19)13(12)17)6-10(15(20)21)8-4-2-1-3-5-8/h1-5,7,10,18-19H,6H2,(H,20,21)

> <INCHI_KEY>
XUABTOLUYWZDOY-UHFFFAOYSA-N

> <FORMULA>
C15H12Br2O4

> <MOLECULAR_WEIGHT>
416.065

> <EXACT_MASS>
413.910235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
32.898685995376425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
4.662727628666666

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.560630211106595

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.6374042695056157

> <JCHEM_PKA_STRONGEST_BASIC>
-6.938134353797946

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
85.84350000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid

> <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  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       5.335  -7.700   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0       5.335  -4.620   0.000  0.00  0.00          Br+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6   15                                                  
CONECT   15   14                                                            
CONECT   16    4   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
3-(2,3-Dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoate	Generator
2-Phenyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)propanoate	Generator

Chemical Formula

C₁₅H₁₂Br₂O₄

Average Mass

416.0650 Da

Monoisotopic Mass

413.91024 Da

IUPAC Name

3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid

Traditional Name

3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(CC1=CC(O)=C(O)C(Br)=C1Br)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H12Br2O4/c16-12-9(7-11(18)14(19)13(12)17)6-10(15(20)21)8-4-2-1-3-5-8/h1-5,7,10,18-19H,6H2,(H,20,21)

InChI Key

XUABTOLUYWZDOY-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
Rhodomela confervoides	LOTUS Database	35616633

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
3-phenylpropanoic-acid
3-halophenol
2-halophenol
3-bromophenol
4-halophenol
2-bromophenol
Catechol
4-bromophenol
Bromobenzene
Halobenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Aryl bromide
Benzenoid
Monocyclic benzene moiety
Aryl halide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organobromide
Organohalogen compound
Organic oxide
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	4.5	ALOGPS
logP	4.66	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	2.64	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.84 m³·mol⁻¹	ChemAxon
Polarizability	32.9 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

11407368

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid (NP0301071)

MOL for NP0301071 (3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid)

3D MOL for NP0301071 (3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid)

3D SDF for NP0301071 (3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid)

3D-SDF for NP0301071 (3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid)

PDB for NP0301071 (3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid)

3D PDB for NP0301071 (3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid)

SMILES for NP0301071 (3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid)

INCHI for NP0301071 (3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid)

Structure for NP0301071 (3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid)

3D Structure for NP0301071 (3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-phenylpropanoic acid)