NP-MRD: Showing NP-Card for Brefelamide (NP0006073)

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Record Information

Version

2.0

Created at

2020-12-09 03:08:51 UTC

Updated at

2021-07-15 16:53:46 UTC

NP-MRD ID

NP0006073

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brefelamide

Provided By

NPAtlas

Description

N-{3-[2-amino-3-(4-hydroxyphenoxy)phenyl]-3-oxopropyl}-4-hydroxybenzamide belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. Brefelamide is found in Dictyostelium and Dictyostelium giganteum. Brefelamide was first documented in 2005 (PMID: 16238318). Based on a literature review very few articles have been published on N-{3-[2-amino-3-(4-hydroxyphenoxy)phenyl]-3-oxopropyl}-4-hydroxybenzamide.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118253D          

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M  END

     RDKit          3D

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  Mrv1652306242118253D          

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 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 15  2  1  0  0  0  0
 29 23  1  0  0  0  0
 11  5  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  6 32  1  0  0  0  0
  7 33  1  0  0  0  0
  9 34  1  0  0  0  0
 10 35  1  0  0  0  0
 11 36  1  0  0  0  0
 12 37  1  0  0  0  0
 13 38  1  0  0  0  0
 14 39  1  0  0  0  0
 18 40  1  0  0  0  0
 18 41  1  0  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
 20 44  1  0  0  0  0
 24 45  1  0  0  0  0
 25 46  1  0  0  0  0
 27 47  1  0  0  0  0
 28 48  1  0  0  0  0
 29 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006073

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(OC2=C(N([H])[H])C(=C([H])C([H])=C2[H])C(=O)C([H])([H])C([H])([H])N([H])C(=O)C2=C([H])C([H])=C(O[H])C([H])=C2[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H20N2O5/c23-21-18(2-1-3-20(21)29-17-10-8-16(26)9-11-17)19(27)12-13-24-22(28)14-4-6-15(25)7-5-14/h1-11,25-26H,12-13,23H2,(H,24,28)

> <INCHI_KEY>
XOHMSOOURABJGK-UHFFFAOYSA-N

> <FORMULA>
C22H20N2O5

> <MOLECULAR_WEIGHT>
392.411

> <EXACT_MASS>
392.137221752

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.82548755758996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-{3-[2-amino-3-(4-hydroxyphenoxy)phenyl]-3-oxopropyl}-4-hydroxybenzamide

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.2310278553333336

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.34779828606095

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.415059243253317

> <JCHEM_PKA_STRONGEST_BASIC>
1.294202679907975

> <JCHEM_POLAR_SURFACE_AREA>
121.88000000000001

> <JCHEM_REFRACTIVITY>
109.53720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{3-[2-amino-3-(4-hydroxyphenoxy)phenyl]-3-oxopropyl}-4-hydroxybenzamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
   -1.9966    0.3719   -1.5523 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173   -1.0547   -1.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2634   -1.6668   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3591   -0.9199   -0.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4340    0.0475    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6358    0.7275    0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8021    1.7045    1.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7891    2.0417    2.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9179    3.0195    3.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6122    1.3392    2.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4165    0.3600    1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3063   -3.0335   -0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066   -3.7871   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525   -3.1468   -1.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9799   -1.7838   -1.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2182   -1.1326   -2.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    0.1208   -2.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4130   -1.9074   -2.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743   -2.0640   -1.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8405   -0.7820   -0.9212 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7421   -0.7472    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1413   -1.8216    0.6974 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2204    0.5450    0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7727    1.7522    0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917    2.9066    0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2476    2.9235    1.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7643    4.0946    2.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6778    1.6873    2.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1935    0.5058    1.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247    0.8758   -0.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393    0.9053   -2.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4603    0.4928   -0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7440    2.2534    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6851    3.9978    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905    1.5803    2.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808   -0.1859    1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1906   -3.5690   -0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062   -4.8605   -1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2030   -3.7666   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2200   -2.9101   -2.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9422   -1.3629   -3.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2335   -2.6504   -1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9113   -2.6122   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5049    0.0782   -1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0317    1.7921   -0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309    3.8548    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5927    4.5456    1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4356    1.6826    2.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5629   -0.4416    2.0498 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  3 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 15  2  1  0
 29 23  1  0
 11  5  1  0
  1 30  1  0
  1 31  1  0
  6 32  1  0
  7 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 24 45  1  0
 25 46  1  0
 27 47  1  0
 28 48  1  0
 29 49  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0      -1.997   0.372  -1.552  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.117  -1.055  -1.399  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.263  -1.667  -0.956  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.359  -0.920  -0.630  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.434   0.048   0.361  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.636   0.728   0.468  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.802   1.704   1.423  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.789   2.042   2.303  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.918   3.019   3.278  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.612   1.339   2.159  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.417   0.360   1.217  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.306  -3.034  -0.843  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.207  -3.787  -1.170  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.052  -3.147  -1.617  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.980  -1.784  -1.741  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.218  -1.133  -2.200  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.251   0.121  -2.293  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.413  -1.907  -2.567  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.374  -2.064  -1.407  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.841  -0.782  -0.921  0.00  0.00           N+0
HETATM   21  C   UNK     0       3.742  -0.747   0.158  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.141  -1.822   0.697  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.220   0.545   0.657  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.773   1.752   0.193  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.292   2.907   0.730  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.248   2.924   1.721  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.764   4.095   2.256  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.678   1.687   2.168  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.194   0.506   1.666  0.00  0.00           C+0
HETATM   30  H   UNK     0      -1.425   0.876  -0.850  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.439   0.905  -2.307  0.00  0.00           H+0
HETATM   32  H   UNK     0      -6.460   0.493  -0.206  0.00  0.00           H+0
HETATM   33  H   UNK     0      -6.744   2.253   1.524  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.685   3.998   3.113  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.791   1.580   2.838  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.481  -0.186   1.122  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.191  -3.569  -0.497  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.206  -4.861  -1.093  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.203  -3.767  -1.865  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.220  -2.910  -2.979  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.942  -1.363  -3.406  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.233  -2.650  -1.771  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.911  -2.612  -0.567  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.505   0.078  -1.375  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.032   1.792  -0.574  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.931   3.855   0.356  0.00  0.00           H+0
HETATM   47  H   UNK     0       6.593   4.546   1.855  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.436   1.683   2.954  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.563  -0.442   2.050  0.00  0.00           H+0
CONECT    1    2   30   31                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7   32                                                  
CONECT    7    6    8   33                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   34                                                       
CONECT   10    8   11   35                                                  
CONECT   11   10    5   36                                                  
CONECT   12    3   13   37                                                  
CONECT   13   12   14   38                                                  
CONECT   14   13   15   39                                                  
CONECT   15   14   16    2                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   40   41                                             
CONECT   19   18   20   42   43                                             
CONECT   20   19   21   44                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25   45                                                  
CONECT   25   24   26   46                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   47                                                       
CONECT   28   26   29   48                                                  
CONECT   29   28   23   49                                                  
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   13                                                            
CONECT   39   14                                                            
CONECT   40   18                                                            
CONECT   41   18                                                            
CONECT   42   19                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   24                                                            
CONECT   46   25                                                            
CONECT   47   27                                                            
CONECT   48   28                                                            
CONECT   49   29                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  102    0
END

RDKit          3D

49 51  0  0  0  0  0  0  0  0999 V2000
   -1.9966    0.3719   -1.5523 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173   -1.0547   -1.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2634   -1.6668   -0.9564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3591   -0.9199   -0.6304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4340    0.0475    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6358    0.7275    0.4678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8021    1.7045    1.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7891    2.0417    2.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9179    3.0195    3.2777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6122    1.3392    2.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4165    0.3600    1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3063   -3.0335   -0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066   -3.7871   -1.1701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525   -3.1468   -1.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9799   -1.7838   -1.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2182   -1.1326   -2.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2507    0.1208   -2.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4130   -1.9074   -2.5665 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743   -2.0640   -1.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8405   -0.7820   -0.9212 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7421   -0.7472    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1413   -1.8216    0.6974 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2204    0.5450    0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7727    1.7522    0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917    2.9066    0.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2476    2.9235    1.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7643    4.0946    2.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6778    1.6873    2.1678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1935    0.5058    1.6662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4247    0.8758   -0.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4393    0.9053   -2.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4603    0.4928   -0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7440    2.2534    1.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6851    3.9978    3.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7905    1.5803    2.8378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808   -0.1859    1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1906   -3.5690   -0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062   -4.8605   -1.0928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2030   -3.7666   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2200   -2.9101   -2.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9422   -1.3629   -3.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2335   -2.6504   -1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9113   -2.6122   -0.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5049    0.0782   -1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0317    1.7921   -0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309    3.8548    0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5927    4.5456    1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4356    1.6826    2.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5629   -0.4416    2.0498 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  3 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 15  2  1  0
 29 23  1  0
 11  5  1  0
  1 30  1  0
  1 31  1  0
  6 32  1  0
  7 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 24 45  1  0
 25 46  1  0
 27 47  1  0
 28 48  1  0
 29 49  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₂₀N₂O₅

Average Mass

392.4110 Da

Monoisotopic Mass

392.13722 Da

IUPAC Name

N-{3-[2-amino-3-(4-hydroxyphenoxy)phenyl]-3-oxopropyl}-4-hydroxybenzamide

Traditional Name

N-{3-[2-amino-3-(4-hydroxyphenoxy)phenyl]-3-oxopropyl}-4-hydroxybenzamide

CAS Registry Number

Not Available

SMILES

NC1=C(C=CC=C1OC1=CC=C(O)C=C1)C(=O)CCNC(=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C22H20N2O5/c23-21-18(2-1-3-20(21)29-17-10-8-16(26)9-11-17)19(27)12-13-24-22(28)14-4-6-15(25)7-5-14/h1-11,25-26H,12-13,23H2,(H,24,28)

InChI Key

XOHMSOOURABJGK-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
Dictyostelium	NPAtlas	16238318
Dictyostelium giganteum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Substituents

Diphenylether
Alkyl-phenylketone
Diaryl ether
Phenylketone
Benzamide
Benzoic acid or derivatives
Phenol ether
Aryl ketone
Aryl alkyl ketone
Aniline or substituted anilines
Benzoyl
Phenoxy compound
Phenol
1-hydroxy-2-unsubstituted benzenoid
Vinylogous amide
Amino acid or derivatives
Ketone
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Organooxygen compound
Amine
Primary amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organonitrogen 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	3.16	ALOGPS
logP	3.23	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.42	ChemAxon
pKa (Strongest Basic)	1.29	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	121.88 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109.54 m³·mol⁻¹	ChemAxon
Polarizability	40.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA000601

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9850265

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11675536

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kikuchi H, Saito Y, Sekiya J, Okano Y, Saito M, Nakahata N, Kubohara Y, Oshima Y: Isolation and synthesis of a new aromatic compound, brefelamide, from dictyostelium cellular slime molds and its inhibitory effect on the proliferation of astrocytoma cells. J Org Chem. 2005 Oct 28;70(22):8854-8. doi: 10.1021/jo051352x. [PubMed:16238318 ]

Showing NP-Card for Brefelamide (NP0006073)

MOL for NP0006073 (Brefelamide)

3D MOL for NP0006073 (Brefelamide)

3D SDF for NP0006073 (Brefelamide)

3D-SDF for NP0006073 (Brefelamide)

PDB for NP0006073 (Brefelamide)

3D PDB for NP0006073 (Brefelamide)

SMILES for NP0006073 (Brefelamide)

INCHI for NP0006073 (Brefelamide)

Structure for NP0006073 (Brefelamide)

3D Structure for NP0006073 (Brefelamide)