NP-MRD: Showing NP-Card for N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide (NP0009994)

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Record Information

Version

2.0

Created at

2021-01-05 19:39:44 UTC

Updated at

2021-07-15 17:04:50 UTC

NP-MRD ID

NP0009994

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide

Provided By

NPAtlas

Description

2,2-Dichloro-N-(3-hydroxy-1-{4-[(1-hydroxyethylidene)amino]phenyl}-1-(1H-indol-3-yl)propan-2-yl)ethanimidic acid belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group. N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide is found in Escherichia coli. Based on a literature review very few articles have been published on 2,2-dichloro-N-(3-hydroxy-1-{4-[(1-hydroxyethylidene)amino]phenyl}-1-(1H-indol-3-yl)propan-2-yl)ethanimidic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106543D          

 50 52  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242106543D          

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   -2.0361   -1.5457    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2065   -3.1710    2.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.5979    1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3812   -0.7855    1.6754 H   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  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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  8 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29  5  1  0  0  0  0
 18 10  1  0  0  0  0
 18 13  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  4 33  1  0  0  0  0
  6 34  1  0  0  0  0
  7 35  1  0  0  0  0
  9 36  1  6  0  0  0
 11 37  1  0  0  0  0
 12 38  1  0  0  0  0
 14 39  1  0  0  0  0
 15 40  1  0  0  0  0
 16 41  1  0  0  0  0
 17 42  1  0  0  0  0
 19 43  1  6  0  0  0
 20 44  1  0  0  0  0
 20 45  1  0  0  0  0
 21 46  1  0  0  0  0
 22 47  1  0  0  0  0
 25 48  1  1  0  0  0
 28 49  1  0  0  0  0
 29 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009994

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]([H])(N([H])C(=O)C([H])(Cl)Cl)[C@@]([H])(C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12)C1=C([H])C([H])=C(N([H])C(=O)C([H])([H])[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H21Cl2N3O3/c1-12(28)25-14-8-6-13(7-9-14)19(18(11-27)26-21(29)20(22)23)16-10-24-17-5-3-2-4-15(16)17/h2-10,18-20,24,27H,11H2,1H3,(H,25,28)(H,26,29)/t18-,19+/m0/s1

> <INCHI_KEY>
IEORQMXIWXLRSB-UHFFFAOYSA-N

> <FORMULA>
C21H21Cl2N3O3

> <MOLECULAR_WEIGHT>
434.32

> <EXACT_MASS>
433.0959969

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
43.741395229188626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-dichloro-N-[(1R,2R)-1-(4-acetamidophenyl)-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl]acetamide

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
2.6929646049999993

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.267643858577905

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.132600446168547

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7674749687817934

> <JCHEM_POLAR_SURFACE_AREA>
94.22

> <JCHEM_REFRACTIVITY>
115.1846

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2-dichloro-N-[(1R,2R)-1-(4-acetamidophenyl)-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    6.6072   -0.7951    1.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1054   -0.6824    1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4567   -0.7237    2.3312 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5130   -0.5421    0.0188 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1431   -0.4292   -0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7267   -0.1670   -1.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070   -0.0661   -1.9117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878   -0.2157   -0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0418   -0.0989   -1.3744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4600    1.2673   -1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5156    2.1656   -2.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136    3.3529   -1.8445 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327    3.3164   -0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5538    4.2457    0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6915    3.8906    1.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137    2.6126    2.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9917    1.6712    1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583    2.0403   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7991   -1.2695   -0.9871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2931   -1.1823   -1.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9620   -0.4788   -0.3815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285   -1.9423    0.2515 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9563   -3.1872    0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694   -3.7525   -0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8114   -3.8338    1.7754 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0248   -5.3755    1.6096 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3763   -4.0307    2.6054 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8306   -0.4731    0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764   -0.5788    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9028   -1.8203    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9036   -0.1215    2.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1178   -0.4547    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1852   -0.5179   -0.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4958   -0.0442   -2.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005    0.1422   -2.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9613   -0.2439   -2.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798    1.9798   -3.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0450    4.2123   -2.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7702    5.2527    0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0189    4.5940    2.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5115    2.2945    3.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739    0.6783    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689   -2.0967   -1.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -0.5801   -2.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7154   -2.1641   -1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5171    0.2519   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -1.5457    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2065   -3.1710    2.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.5979    1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3812   -0.7855    1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
  8 28  1  0
 28 29  2  0
 29  5  1  0
 18 10  1  0
 18 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  6
 11 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  6
 20 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  1
 28 49  1  0
 29 50  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  C   UNK     0       6.607  -0.795   1.414  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.105  -0.682   1.273  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.457  -0.724   2.331  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.513  -0.542   0.019  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.143  -0.429  -0.287  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.727  -0.167  -1.591  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.407  -0.066  -1.912  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.388  -0.216  -0.973  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.042  -0.099  -1.374  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.460   1.267  -1.192  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.516   2.166  -2.274  0.00  0.00           C+0
HETATM   12  N   UNK     0      -1.914   3.353  -1.845  0.00  0.00           N+0
HETATM   13  C   UNK     0      -2.133   3.316  -0.534  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.554   4.246   0.407  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.692   3.891   1.723  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.414   2.613   2.123  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.992   1.671   1.197  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.858   2.040  -0.117  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.799  -1.270  -0.987  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.293  -1.182  -1.384  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.962  -0.479  -0.382  0.00  0.00           O+0
HETATM   22  N   UNK     0      -1.629  -1.942   0.252  0.00  0.00           N+0
HETATM   23  C   UNK     0      -0.956  -3.187   0.451  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.469  -3.753  -0.540  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.811  -3.834   1.775  0.00  0.00           C+0
HETATM   26 Cl   UNK     0       0.025  -5.375   1.610  0.00  0.00          Cl+0
HETATM   27 Cl   UNK     0      -2.376  -4.031   2.605  0.00  0.00          Cl+0
HETATM   28  C   UNK     0       0.831  -0.473   0.305  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.176  -0.579   0.646  0.00  0.00           C+0
HETATM   30  H   UNK     0       6.903  -1.820   1.714  0.00  0.00           H+0
HETATM   31  H   UNK     0       6.904  -0.122   2.240  0.00  0.00           H+0
HETATM   32  H   UNK     0       7.118  -0.455   0.500  0.00  0.00           H+0
HETATM   33  H   UNK     0       5.185  -0.518  -0.817  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.496  -0.044  -2.349  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.101   0.142  -2.940  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.961  -0.244  -2.530  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.280   1.980  -3.327  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.045   4.212  -2.432  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.770   5.253   0.077  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.019   4.594   2.482  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.511   2.295   3.157  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.774   0.678   1.481  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.469  -2.097  -1.738  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.395  -0.580  -2.309  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.715  -2.164  -1.570  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.517   0.252  -0.734  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.036  -1.546   1.117  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.207  -3.171   2.465  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.102  -0.598   1.096  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.381  -0.786   1.675  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6   29                                                  
CONECT    6    5    7   34                                                  
CONECT    7    6    8   35                                                  
CONECT    8    7    9   28                                                  
CONECT    9    8   10   19   36                                             
CONECT   10    9   11   18                                                  
CONECT   11   10   12   37                                                  
CONECT   12   11   13   38                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   39                                                  
CONECT   15   14   16   40                                                  
CONECT   16   15   17   41                                                  
CONECT   17   16   18   42                                                  
CONECT   18   17   10   13                                                  
CONECT   19    9   20   22   43                                             
CONECT   20   19   21   44   45                                             
CONECT   21   20   46                                                       
CONECT   22   19   23   47                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   48                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    8   29   49                                                  
CONECT   29   28    5   50                                                  
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    4                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    9                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   25                                                            
CONECT   49   28                                                            
CONECT   50   29                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
    6.6072   -0.7951    1.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1054   -0.6824    1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4567   -0.7237    2.3312 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5130   -0.5421    0.0188 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1431   -0.4292   -0.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7267   -0.1670   -1.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4070   -0.0661   -1.9117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3878   -0.2157   -0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0418   -0.0989   -1.3744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4600    1.2673   -1.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5156    2.1656   -2.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9136    3.3529   -1.8445 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327    3.3164   -0.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5538    4.2457    0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6915    3.8906    1.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4137    2.6126    2.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9917    1.6712    1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8583    2.0403   -0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7991   -1.2695   -0.9871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2931   -1.1823   -1.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9620   -0.4788   -0.3815 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6285   -1.9423    0.2515 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9563   -3.1872    0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694   -3.7525   -0.5400 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8114   -3.8338    1.7754 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0248   -5.3755    1.6096 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3763   -4.0307    2.6054 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8306   -0.4731    0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764   -0.5788    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9028   -1.8203    1.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9036   -0.1215    2.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1178   -0.4547    0.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1852   -0.5179   -0.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4958   -0.0442   -2.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005    0.1422   -2.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9613   -0.2439   -2.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2798    1.9798   -3.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0450    4.2123   -2.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7702    5.2527    0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0189    4.5940    2.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5115    2.2945    3.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7739    0.6783    1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4689   -2.0967   -1.7375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -0.5801   -2.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7154   -2.1641   -1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5171    0.2519   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -1.5457    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2065   -3.1710    2.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -0.5979    1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3812   -0.7855    1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
  8 28  1  0
 28 29  2  0
 29  5  1  0
 18 10  1  0
 18 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  6 34  1  0
  7 35  1  0
  9 36  1  6
 11 37  1  0
 12 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  6
 20 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 25 48  1  1
 28 49  1  0
 29 50  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2,2-Dichloro-N-(3-hydroxy-1-{4-[(1-hydroxyethylidene)amino]phenyl}-1-(1H-indol-3-yl)propan-2-yl)ethanimidate	Generator
N-(1-(4-(Acetylamino)phenyl)-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl)-2,2-dichloroacetamide	MeSH
APHIPD CPD	MeSH

Chemical Formula

C₂₁H₂₁Cl₂N₃O₃

Average Mass

434.3200 Da

Monoisotopic Mass

433.09600 Da

IUPAC Name

2,2-dichloro-N-[(1R,2R)-1-(4-acetamidophenyl)-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl]acetamide

Traditional Name

2,2-dichloro-N-[(1R,2R)-1-(4-acetamidophenyl)-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl]acetamide

CAS Registry Number

Not Available

SMILES

CC(=O)NC1=CC=C(C=C1)C(C(CO)NC(=O)C(Cl)Cl)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C21H21Cl2N3O3/c1-12(28)25-14-8-6-13(7-9-14)19(18(11-27)26-21(29)20(22)23)16-10-24-17-5-3-2-4-15(16)17/h2-10,18-20,24,27H,11H2,1H3,(H,25,28)(H,26,29)

InChI Key

IEORQMXIWXLRSB-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
Escherichia coli	NPAtlas	21534044

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Acetanilides

Alternative Parents

Substituents

Acetanilide
3-alkylindole
Indole
N-acetylarylamine
Indole or derivatives
N-arylamide
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Alkyl chloride
Alkyl halide
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	3.26	ALOGPS
logP	2.69	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	10.13	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	94.22 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	115.18 m³·mol⁻¹	ChemAxon
Polarizability	43.74 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

NPA008127

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78434810

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53350156

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide (NP0009994)

MOL for NP0009994 (N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide)

3D MOL for NP0009994 (N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide)

3D SDF for NP0009994 (N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide)

3D-SDF for NP0009994 (N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide)

PDB for NP0009994 (N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide)

3D PDB for NP0009994 (N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide)

SMILES for NP0009994 (N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide)

INCHI for NP0009994 (N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide)

Structure for NP0009994 (N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide)

3D Structure for NP0009994 (N-{1-[4-(acetylamino)phenyl]-3-hydroxy-1-(1H-indol-3-yl)propan-2-yl}-2,2-dichloroacetamide)