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Showing NP-Card for n-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide (NP0221672)

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Record Information
Version2.0
Created at2022-09-05 23:18:56 UTC
Updated at2022-09-05 23:18:57 UTC
NP-MRD IDNP0221672
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide
DescriptionN-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. N-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0221672 (n-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide)


  Mrv1533004261500182D          

 25 26  0  0  0  0            999 V2000
    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 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 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
    3.5724   -6.1875    0.0000 C   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 O   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
    2.1434   -5.3625    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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 N   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 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 Br  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  2  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
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 17 25  1  0  0  0  0
M  END
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3D MOL for NP0221672 (n-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide)

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3D SDF for NP0221672 (n-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide)

  Mrv1533004261500182D          

 25 26  0  0  0  0            999 V2000
    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 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 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
    3.5724   -6.1875    0.0000 C   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 O   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
    2.1434   -5.3625    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
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 N   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 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 Br  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  2  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
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
  5 11  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 17 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221672

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=CC1=CC=C(O)C=C1)C(=O)NC=CC1=CC(Br)=C(O)C(Br)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H15Br2NO4/c1-25-16(10-11-2-4-13(22)5-3-11)18(24)21-7-6-12-8-14(19)17(23)15(20)9-12/h2-10,22-23H,1H3,(H,21,24)

> <INCHI_KEY>
DIAAHMADUFVQJZ-UHFFFAOYSA-N

> <FORMULA>
C18H15Br2NO4

> <MOLECULAR_WEIGHT>
469.129

> <EXACT_MASS>
466.936784

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
40.25040915499845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide

> <ALOGPS_LOGP>
4.29

> <JCHEM_LOGP>
4.185177394666665

> <ALOGPS_LOGS>
-5.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.217122854065847

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.736551790700564

> <JCHEM_PKA_STRONGEST_BASIC>
-4.352132658678867

> <JCHEM_POLAR_SURFACE_AREA>
78.79

> <JCHEM_REFRACTIVITY>
105.16550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0221672 (n-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide)
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PDB for NP0221672 (n-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide)
HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335 -13.860   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20 Br   UNK     0      -1.334   2.310   0.000  0.00  0.00          Br+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   24 Br   UNK     0       4.001   2.310   0.000  0.00  0.00          Br+0
HETATM   25  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5                                                       
CONECT   12    3   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   17                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

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3D PDB for NP0221672 (n-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide)
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SMILES for NP0221672 (n-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide)
COC(=CC1=CC=C(O)C=C1)C(=O)NC=CC1=CC(Br)=C(O)C(Br)=C1
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INCHI for NP0221672 (n-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide)
InChI=1S/C18H15Br2NO4/c1-25-16(10-11-2-4-13(22)5-3-11)18(24)21-7-6-12-8-14(19)17(23)15(20)9-12/h2-10,22-23H,1H3,(H,21,24)
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View in JSmol
SynonymsNot Available
Chemical FormulaC18H15Br2NO4
Average Mass469.1290 Da
Monoisotopic Mass466.93678 Da
IUPAC NameN-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide
Traditional NameN-[2-(3,5-dibromo-4-hydroxyphenyl)ethenyl]-3-(4-hydroxyphenyl)-2-methoxyprop-2-enamide
CAS Registry NumberNot Available
SMILES
COC(=CC1=CC=C(O)C=C1)C(=O)NC=CC1=CC(Br)=C(O)C(Br)=C1
InChI Identifier
InChI=1S/C18H15Br2NO4/c1-25-16(10-11-2-4-13(22)5-3-11)18(24)21-7-6-12-8-14(19)17(23)15(20)9-12/h2-10,22-23H,1H3,(H,21,24)
InChI KeyDIAAHMADUFVQJZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassHydroxycinnamic acids and derivatives  
Direct ParentCoumaric acids and derivatives  
Alternative Parents
Substituents
  • Cinnamic acid amide
    • 

  • Coumaric acid or derivatives
    • 

  • Styrene
    • 

  • 2-halophenol
    • 

  • 2-bromophenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Bromobenzene
    • 

  • Phenol
    • 

  • Halobenzene
    • 

  • Aryl bromide
    • 

  • Aryl halide
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organobromide
    • 

  • Organohalogen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.29ALOGPS
logP4.19ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)6.74ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.79 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity105.17 m³·mol⁻¹ChemAxon
Polarizability40.25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73085466  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]