NP-MRD: Showing NP-Card for Psammaplin A (NP0026312)

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Record Information

Version

2.0

Created at

2021-06-19 18:12:48 UTC

Updated at

2021-06-29 23:51:46 UTC

NP-MRD ID

NP0026312

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Psammaplin A

Provided By

JEOL Database JEOL Logo

Description

Psammaplin A is also known as bisprasin. Psammaplin A is found in Aplysinella rhax, Psammaplysilla sp., Pseudoceratina purpurea and Tribullus terrestris. Psammaplin A was first documented in 2019 (PMID: 31720371). Based on a literature review a small amount of articles have been published on Psammaplin A (PMID: 33636429) (PMID: 33488962) (PMID: 32697400) (PMID: 32576661).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120123D          

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     RDKit          3D

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M  END


  Mrv1652306192120123D          

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    1.7326   -0.6349    1.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7859    1.5457    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3660   -0.3151    1.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427   -3.9553    1.7081 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1803   -3.6558    2.5691 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2581   -4.5354   -0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264   -5.2976   -1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8358    1.8734   -0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6012    2.5068   -0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3308   -0.9302    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0  0  0  0
 32 30  2  0  0  0  0
  8  9  1  0  0  0  0
 30 29  1  0  0  0  0
 25  2  1  0  0  0  0
 29 28  2  0  0  0  0
 28 27  1  0  0  0  0
  9 10  1  0  0  0  0
 15 22  2  0  0  0  0
  4  5  1  0  0  0  0
 22 20  1  0  0  0  0
 10 11  1  0  0  0  0
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 26 25  1  0  0  0  0
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  5  6  1  0  0  0  0
 32 33  1  0  0  0  0
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  2  3  1  0  0  0  0
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  6  7  1  0  0  0  0
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 34 32  1  0  0  0  0
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 31 58  1  0  0  0  0
 19 51  1  0  0  0  0
 36 60  1  0  0  0  0
 24 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026312

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\N=C(\C(=O)N([H])C([H])([H])C([H])([H])SSC([H])([H])C([H])([H])N([H])C(=O)C(=N\O[H])\C([H])([H])C1=C([H])C(Br)=C(O[H])C([H])=C1[H])C([H])([H])C1=C([H])C(Br)=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H24Br2N4O6S2/c23-15-9-13(1-3-19(15)29)11-17(27-33)21(31)25-5-7-35-36-8-6-26-22(32)18(28-34)12-14-2-4-20(30)16(24)10-14/h1-4,9-10,29-30,33-34H,5-8,11-12H2,(H,25,31)(H,26,32)/b27-17+,28-18+

> <INCHI_KEY>
LMAFSGDNHVBIHU-XUIWWLCJSA-N

> <FORMULA>
C22H24Br2N4O6S2

> <MOLECULAR_WEIGHT>
664.38

> <EXACT_MASS>
661.950403

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
54.23291158642729

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(3-bromo-4-hydroxyphenyl)-N-[2-({2-[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
4.081383007333332

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.852881990873328

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.2739309660501705

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3419066980406855

> <JCHEM_POLAR_SURFACE_AREA>
163.84

> <JCHEM_REFRACTIVITY>
149.0862

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(3-bromo-4-hydroxyphenyl)-N-[2-({2-[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
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  3  4  1  0
 32 30  2  0
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 30 29  1  0
 25  2  1  0
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 25 35  2  0
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 19 51  1  0
 36 60  1  0
 24 53  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0       4.457  -2.660   1.089  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.417  -3.268   0.893  0.00  0.00           C+0
HETATM    3  N   UNK     0       3.187  -4.124  -0.158  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.138  -4.327  -1.228  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.135  -3.199  -2.265  0.00  0.00           C+0
HETATM    6  S   UNK     0       2.737  -3.250  -3.456  0.00  0.00           S+0
HETATM    7  S   UNK     0       1.056  -3.012  -2.296  0.00  0.00           S+0
HETATM    8  C   UNK     0       1.001  -1.207  -2.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.582  -0.395  -3.227  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.739  -0.752  -3.700  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.886  -0.298  -3.095  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.951   0.544  -2.213  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.144  -1.005  -3.586  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.135  -1.397  -2.512  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.550  -2.403  -1.543  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.455  -2.096  -0.178  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.881  -3.000   0.717  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.405  -4.220   0.254  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.834  -5.061   1.172  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.509  -4.549  -1.098  0.00  0.00           C+0
HETATM   21 Br   UNK     0      -1.861  -6.208  -1.742  0.00  0.00          Br+0
HETATM   22  C   UNK     0      -3.085  -3.648  -1.996  0.00  0.00           C+0
HETATM   23  N   UNK     0      -3.231  -1.254  -4.864  0.00  0.00           N+0
HETATM   24  O   UNK     0      -4.408  -1.940  -5.178  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.210  -3.085   1.815  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.231  -1.865   2.712  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.733  -0.635   1.988  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.620   0.173   1.260  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.147   1.262   0.525  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.786   1.546   0.510  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.371   2.574  -0.289  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.103   0.779   1.263  0.00  0.00           C+0
HETATM   33 Br   UNK     0      -1.946   1.205   1.320  0.00  0.00          Br+0
HETATM   34  C   UNK     0       0.366  -0.315   1.992  0.00  0.00           C+0
HETATM   35  N   UNK     0       1.243  -3.955   1.708  0.00  0.00           N+0
HETATM   36  O   UNK     0       0.180  -3.656   2.569  0.00  0.00           O+0
HETATM   37  H   UNK     0       2.258  -4.535  -0.219  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.926  -5.298  -1.688  0.00  0.00           H+0
HETATM   39  H   UNK     0       5.135  -4.385  -0.775  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.160  -2.213  -1.790  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.043  -3.286  -2.872  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.280  -1.052  -1.191  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.978  -0.875  -1.638  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.578   0.670  -2.969  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.280  -0.532  -4.059  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.836  -1.440  -4.440  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.431  -0.483  -1.985  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.052  -1.815  -2.937  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.819  -1.142   0.197  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.803  -2.744   1.770  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.591  -5.875   0.688  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.164  -3.907  -3.050  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.368  -2.002  -6.152  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.629  -2.041   3.610  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.250  -1.696   3.080  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.686  -0.050   1.248  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.836   1.873  -0.051  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.601   2.507  -0.359  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.331  -0.930   2.558  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.538  -4.243   2.244  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   25    3    1                                                  
CONECT    3    4    2   37                                                  
CONECT    4    3    5   38   39                                             
CONECT    5    4    6   40   41                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    9    7   42   43                                             
CONECT    9    8   10   44   45                                             
CONECT   10    9   11   46                                                  
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11   14   23                                                  
CONECT   14   13   15   47   48                                             
CONECT   15   22   16   14                                                  
CONECT   16   17   15   49                                                  
CONECT   17   18   16   50                                                  
CONECT   18   20   17   19                                                  
CONECT   19   18   51                                                       
CONECT   20   22   18   21                                                  
CONECT   21   20                                                            
CONECT   22   15   20   52                                                  
CONECT   23   13   24                                                       
CONECT   24   23   53                                                       
CONECT   25    2   26   35                                                  
CONECT   26   25   27   54   55                                             
CONECT   27   28   26   34                                                  
CONECT   28   29   27   56                                                  
CONECT   29   30   28   57                                                  
CONECT   30   32   29   31                                                  
CONECT   31   30   58                                                       
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   27   32   59                                                  
CONECT   35   25   36                                                       
CONECT   36   35   60                                                       
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    8                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   14                                                            
CONECT   48   14                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   19                                                            
CONECT   52   22                                                            
CONECT   53   24                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   28                                                            
CONECT   57   29                                                            
CONECT   58   31                                                            
CONECT   59   34                                                            
CONECT   60   36                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  122    0
END

RDKit          3D

60 61  0  0  0  0  0  0  0  0999 V2000
    4.4572   -2.6598    1.0892 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171   -3.2680    0.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1869   -4.1238   -0.1582 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1382   -4.3269   -1.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1352   -3.1993   -2.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7372   -3.2499   -3.4562 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0564   -3.0124   -2.2964 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013   -1.2067   -1.9995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5817   -0.3953   -3.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7391   -0.7522   -3.6997 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864   -0.2978   -3.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9509    0.5443   -2.2134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1444   -1.0050   -3.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1346   -1.3974   -2.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5502   -2.4030   -1.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4550   -2.0959   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8808   -2.9997    0.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4050   -4.2202    0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8341   -5.0613    1.1720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5089   -4.5494   -1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8605   -6.2082   -1.7425 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0854   -3.6482   -1.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312   -1.2536   -4.8641 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4082   -1.9401   -5.1782 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2099   -3.0848    1.8152 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313   -1.8654    2.7120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7326   -0.6349    1.9878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6198    0.1729    1.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    1.2615    0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7859    1.5457    0.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711    2.5740   -0.2886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1027    0.7788    1.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460    1.2046    1.3197 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.3660   -0.3151    1.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427   -3.9553    1.7081 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1803   -3.6558    2.5691 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2581   -4.5354   -0.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264   -5.2976   -1.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1349   -4.3852   -0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1604   -2.2128   -1.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430   -3.2861   -2.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804   -1.0520   -1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9785   -0.8752   -1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5780    0.6697   -2.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796   -0.5322   -4.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364   -1.4399   -4.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4314   -0.4825   -1.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0524   -1.8147   -2.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8192   -1.1416    0.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8034   -2.7443    1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5909   -5.8745    0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643   -3.9067   -3.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3680   -2.0019   -6.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6290   -2.0407    3.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2499   -1.6960    3.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6861   -0.0500    1.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358    1.8734   -0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6012    2.5068   -0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3308   -0.9302    2.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5378   -4.2426    2.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
 32 30  2  0
  8  9  1  0
 30 29  1  0
 25  2  1  0
 29 28  2  0
 28 27  1  0
  9 10  1  0
 15 22  2  0
  4  5  1  0
 22 20  1  0
 10 11  1  0
 20 18  2  0
 26 25  1  0
 18 17  1  0
 11 13  1  0
 17 16  2  0
 16 15  1  0
  5  6  1  0
 32 33  1  0
 13 14  1  0
 30 31  1  0
  2  3  1  0
 18 19  1  0
 26 27  1  0
 20 21  1  0
  6  7  1  0
 25 35  2  0
 14 15  1  0
 35 36  1  0
 13 23  2  0
 27 34  2  0
 23 24  1  0
  7  8  1  0
  2  1  2  0
 34 32  1  0
 11 12  2  0
 26 54  1  0
 26 55  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  0
  5 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
  9 45  1  0
 10 46  1  0
 14 47  1  0
 14 48  1  0
 34 59  1  0
 29 57  1  0
 28 56  1  0
 22 52  1  0
 17 50  1  0
 16 49  1  0
 31 58  1  0
 19 51  1  0
 36 60  1  0
 24 53  1  0
M  END

View in JSmol

Synonyms

Value	Source
Bisprasin	MeSH

Chemical Formula

C₂₂H₂₄Br₂N₄O₆S₂

Average Mass

664.3800 Da

Monoisotopic Mass

661.95040 Da

IUPAC Name

(2E)-3-(3-bromo-4-hydroxyphenyl)-N-[2-({2-[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide

Traditional Name

(2E)-3-(3-bromo-4-hydroxyphenyl)-N-[2-({2-[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide

CAS Registry Number

Not Available

SMILES

[H]O\N=C(\C(=O)N([H])C([H])([H])C([H])([H])SSC([H])([H])C([H])([H])N([H])C(=O)C(=N\O[H])\C([H])([H])C1=C([H])C(Br)=C(O[H])C([H])=C1[H])C([H])([H])C1=C([H])C(Br)=C(O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C22H24Br2N4O6S2/c23-15-9-13(1-3-19(15)29)11-17(27-33)21(31)25-5-7-35-36-8-6-26-22(32)18(28-34)12-14-2-4-20(30)16(24)10-14/h1-4,9-10,29-30,33-34H,5-8,11-12H2,(H,25,31)(H,26,32)/b27-17+,28-18+

InChI Key

LMAFSGDNHVBIHU-XUIWWLCJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aplysinella rhax	Animalia	KNApSAcK
Psammaplysilla sp.	-	KNApSAcK
Pseudoceratina purpurea	JEOL database	Pina, I. C., et al, J. Org. Chem. 68, 3866 (2003)
Tribullus terrestris	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-bromophenols. These are bromophenols carrying a iodine at the C2 position of the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

2-bromophenol
1-hydroxy-2-unsubstituted benzenoid
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Fatty acyl
Fatty amide
Ketoxime
Carboxamide group
Dialkyldisulfide
Secondary carboxylic acid amide
Organic disulfide
Carboxylic acid derivative
Sulfenyl compound
Oxime
Organooxygen compound
Organosulfur compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organohalogen compound
Organobromide
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	3.5	ALOGPS
logP	4.08	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	6.27	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	163.84 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	149.09 m³·mol⁻¹	ChemAxon
Polarizability	54.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

4912121

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6400741

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Byun WS, Kim WK, Han HJ, Chung HJ, Jang K, Kim HS, Kim S, Kim D, Bae ES, Park S, Lee J, Park HG, Lee SK: Targeting Histone Methyltransferase DOT1L by a Novel Psammaplin A Analog Inhibits Growth and Metastasis of Triple-Negative Breast Cancer. Mol Ther Oncolytics. 2019 Oct 1;15:140-152. doi: 10.1016/j.omto.2019.09.005. eCollection 2019 Dec 20. [PubMed:31720371 ]
Ju Han H, Sub Byun W, Ho Lee G, Kyung Kim W, Jang K, Yang S, Yang J, Woo Ha M, Hong S, Lee J, Shin J, Bong Oh K, Kook Lee S, Park HG: Synthesis and biological activity of selenopsammaplin A and its analogues as antitumor agents with DOT1L inhibitory activity. Bioorg Med Chem. 2021 Apr 1;35:116072. doi: 10.1016/j.bmc.2021.116072. Epub 2021 Feb 11. [PubMed:33636429 ]
Bao Y, Xu Q, Wang L, Wei Y, Hu B, Wang J, Liu D, Zhao L, Jing Y: Studying Histone Deacetylase Inhibition and Apoptosis Induction of Psammaplin A Monomers with Modified Thiol Group. ACS Med Chem Lett. 2021 Jan 5;12(1):39-47. doi: 10.1021/acsmedchemlett.0c00369. eCollection 2021 Jan 14. [PubMed:33488962 ]
Oluwabusola ET, Tabudravu JN, Al Maqbali KS, Annang F, Perez-Moreno G, Reyes F, Jaspars M: Antiparasitic Activity of Bromotyrosine Alkaloids and New Analogues Isolated from the Fijian Marine Sponge Aplysinella rhax. Chem Biodivers. 2020 Oct;17(10):e2000335. doi: 10.1002/cbdv.202000335. Epub 2020 Sep 29. [PubMed:32697400 ]
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Showing NP-Card for Psammaplin A (NP0026312)

MOL for NP0026312 (Psammaplin A)

3D MOL for NP0026312 (Psammaplin A)

3D SDF for NP0026312 (Psammaplin A)

3D-SDF for NP0026312 (Psammaplin A)

PDB for NP0026312 (Psammaplin A)

3D PDB for NP0026312 (Psammaplin A)

SMILES for NP0026312 (Psammaplin A)

INCHI for NP0026312 (Psammaplin A)

Structure for NP0026312 (Psammaplin A)

3D Structure for NP0026312 (Psammaplin A)