NP-MRD: Showing NP-Card for Stephacidin A (NP0004444)

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Record Information

Version

2.0

Created at

2020-12-09 01:54:19 UTC

Updated at

2021-07-15 16:49:12 UTC

NP-MRD ID

NP0004444

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Stephacidin A

Provided By

NPAtlas

Description

26-Hydroxy-9,9,16,16-tetramethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]Hexacosa-3(15),4(13),5,7(12),10,25-hexaen-24-one belongs to the class of organic compounds known as pyrroloquinolines. Pyrroloquinolines are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline. Stephacidin A is found in Aspergillus ochraceus and Aspergillus taichungensis. Stephacidin A was first documented in 2002 (PMID: 12465964). Based on a literature review very few articles have been published on 26-hydroxy-9,9,16,16-tetramethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0¹,¹⁷.0³,¹⁵.0⁴,¹³.0⁷,¹².0¹⁹,²³]Hexacosa-3(15),4(13),5,7(12),10,25-hexaen-24-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118063D          

 61 67  0  0  0  0            999 V2000
    6.6621   -1.2498   -1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1028   -0.7826   -0.2797 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2957   -0.5795    0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4672    0.5175   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1986    0.7574   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3304   -0.2888    0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9082   -1.5262    0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0995   -2.5366    0.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2495    1.0920    0.4412 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0034   -0.0124    0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2534    1.6467    0.9304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1470    2.5435    2.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0592    1.3374   -0.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  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  2  0  0  0  0
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M  END

     RDKit          3D

 61 67  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242118063D          

 61 67  0  0  0  0            999 V2000
    6.6621   -1.2498   -1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1028   -0.7826   -0.2797 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.0995   -2.5366    0.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  6  0  0  0
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  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
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 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 15 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
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  7 32  1  0  0  0  0
 32  2  1  0  0  0  0
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 29 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C3C([H])=C([H])C(OC3=C([H])C([H])=C2C2=C1C(C([H])([H])[H])(C([H])([H])[H])[C@@]1([H])C([H])([H])[C@@]34N(C(=O)[C@@]1(N([H])C3=O)C2([H])[H])C([H])([H])C([H])([H])C4([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H29N3O3/c1-23(2)10-8-15-17(32-23)7-6-14-16-12-26-18(24(3,4)20(16)27-19(14)15)13-25(21(30)28-26)9-5-11-29(25)22(26)31/h6-8,10,18,27H,5,9,11-13H2,1-4H3,(H,28,30)/t18-,25-,26-/m1/s1

> <INCHI_KEY>
YCWBTRJVYADFLQ-UHFFFAOYSA-N

> <FORMULA>
C26H29N3O3

> <MOLECULAR_WEIGHT>
431.536

> <EXACT_MASS>
431.220891806

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
48.5448321782757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,17R,19R)-9,9,16,16-tetramethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0^{1,17}.0^{3,15}.0^{4,13}.0^{7,12}.0^{19,23}]hexacosa-3(15),4,6,10,12-pentaene-24,26-dione

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
2.8902196629999994

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.402976110408233

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.768018043601023

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1973723023584255

> <JCHEM_POLAR_SURFACE_AREA>
74.43

> <JCHEM_REFRACTIVITY>
121.86399999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,17R,19R)-9,9,16,16-tetramethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0^{1,17}.0^{3,15}.0^{4,13}.0^{7,12}.0^{19,23}]hexacosa-3(15),4,6,10,12-pentaene-24,26-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 32  2  1  0
 14  6  2  0
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 29 61  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       6.662  -1.250  -1.631  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.103  -0.783  -0.280  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.296  -0.580   0.650  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.467   0.518  -0.478  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.199   0.757  -0.220  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.330  -0.289   0.293  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.908  -1.526   0.488  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.099  -2.537   0.975  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.773  -2.290   1.246  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.216  -1.047   1.043  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.033  -0.475   1.203  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.026   0.835   0.838  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.250   1.092   0.441  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.003  -0.012   0.555  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.253   1.647   0.930  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.147   2.543   2.177  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.174   2.641  -0.242  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.520   0.898   0.900  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.476   1.335  -0.220  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.455   0.199  -0.476  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.604   0.575  -1.316  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.456  -0.201  -2.577  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.313  -1.134  -2.444  0.00  0.00           C+0
HETATM   24  N   UNK     0      -3.659  -0.804  -1.220  0.00  0.00           N+0
HETATM   25  C   UNK     0      -2.481  -1.143  -0.501  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.532  -1.826  -0.911  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.427  -0.601   0.883  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.282  -1.124   1.694  0.00  0.00           C+0
HETATM   29  N   UNK     0      -3.692  -1.078   1.475  0.00  0.00           N+0
HETATM   30  C   UNK     0      -4.835  -0.502   0.798  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.989  -0.582   1.226  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.246  -1.757   0.211  0.00  0.00           O+0
HETATM   33  H   UNK     0       5.950  -1.970  -2.064  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.619  -1.783  -1.474  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.799  -0.392  -2.297  0.00  0.00           H+0
HETATM   36  H   UNK     0       7.899  -1.490   0.762  0.00  0.00           H+0
HETATM   37  H   UNK     0       6.940  -0.185   1.627  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.939   0.228   0.219  0.00  0.00           H+0
HETATM   39  H   UNK     0       6.059   1.337  -0.857  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.762   1.747  -0.383  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.512  -3.521   1.143  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.134  -3.070   1.625  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.550   2.029   0.105  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.960   3.274   2.218  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.185   1.834   3.041  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.139   3.005   2.218  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.102   3.248  -0.305  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.353   3.352   0.026  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.934   2.132  -1.186  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.096   1.181   1.835  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.901   1.480  -1.158  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.990   2.279   0.037  0.00  0.00           H+0
HETATM   53  H   UNK     0      -6.566   0.373  -0.772  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.577   1.678  -1.489  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.302   0.538  -3.414  0.00  0.00           H+0
HETATM   56  H   UNK     0      -6.428  -0.725  -2.768  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.648  -1.056  -3.343  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.709  -2.186  -2.463  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.476  -0.900   2.751  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.243  -2.214   1.562  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.752  -1.726   2.257  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3    4   32                                             
CONECT    3    2   36   37   38                                             
CONECT    4    2    5   39                                                  
CONECT    5    4    6   40                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   32                                                  
CONECT    8    7    9   41                                                  
CONECT    9    8   10   42                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14   43                                                  
CONECT   14   13    6   10                                                  
CONECT   15   12   16   17   18                                             
CONECT   16   15   44   45   46                                             
CONECT   17   15   47   48   49                                             
CONECT   18   15   19   27   50                                             
CONECT   19   18   20   51   52                                             
CONECT   20   19   21   24   30                                             
CONECT   21   20   22   53   54                                             
CONECT   22   21   23   55   56                                             
CONECT   23   22   24   57   58                                             
CONECT   24   23   25   20                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   18                                             
CONECT   28   27   11   59   60                                             
CONECT   29   27   30   61                                                  
CONECT   30   29   31   20                                                  
CONECT   31   30                                                            
CONECT   32    7    2                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43   13                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   21                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   23                                                            
CONECT   58   23                                                            
CONECT   59   28                                                            
CONECT   60   28                                                            
CONECT   61   29                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  134    0
END

RDKit          3D

61 67  0  0  0  0  0  0  0  0999 V2000
    6.6621   -1.2498   -1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1028   -0.7826   -0.2797 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2957   -0.5795    0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4672    0.5175   -0.4777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1986    0.7574   -0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3304   -0.2888    0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9082   -1.5262    0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0995   -2.5366    0.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7729   -2.2903    1.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2157   -1.0469    1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0325   -0.4754    1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0263    0.8351    0.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2495    1.0920    0.4412 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0034   -0.0124    0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2534    1.6467    0.9304 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1470    2.5435    2.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1739    2.6413   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5201    0.8981    0.9000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4758    1.3351   -0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4551    0.1986   -0.4761 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6042    0.5748   -1.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4563   -0.2010   -2.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3129   -1.1340   -2.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6590   -0.8036   -1.2196 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814   -1.1431   -0.5009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.8256   -0.9106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4272   -0.6008    0.8826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2817   -1.1239    1.6943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6916   -1.0779    1.4753 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8346   -0.5020    0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9893   -0.5815    1.2257 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2461   -1.7570    0.2106 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -1.9696   -2.0640 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6194   -1.7829   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7991   -0.3924   -2.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8991   -1.4895    0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9398   -0.1854    1.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9386    0.2281    0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0592    1.3374   -0.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7621    1.7471   -0.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5118   -3.5205    1.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1339   -3.0702    1.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5497    2.0290    0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9605    3.2738    2.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1851    1.8341    3.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1393    3.0051    2.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1017    3.2481   -0.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529    3.3522    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9344    2.1322   -1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0959    1.1814    1.8346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9005    1.4802   -1.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9900    2.2792    0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5655    0.3732   -0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5774    1.6777   -1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3016    0.5375   -3.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4279   -0.7247   -2.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6475   -1.0561   -3.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7091   -2.1855   -2.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757   -0.9004    2.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2434   -2.2138    1.5617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7522   -1.7263    2.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  1
 15 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 27 25  1  6
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  2  0
  7 32  1  0
 32  2  1  0
 14  6  2  0
 27 18  1  0
 14 10  1  0
 24 20  1  0
 28 11  1  0
 20 30  1  1
  1 33  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  0
  3 37  1  0
  3 38  1  0
  4 39  1  0
  5 40  1  0
  8 41  1  0
  9 42  1  0
 13 43  1  0
 16 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 17 49  1  0
 18 50  1  1
 19 51  1  0
 19 52  1  0
 21 53  1  0
 21 54  1  0
 22 55  1  0
 22 56  1  0
 23 57  1  0
 23 58  1  0
 28 59  1  0
 28 60  1  0
 29 61  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₆H₂₉N₃O₃

Average Mass

431.5360 Da

Monoisotopic Mass

431.22089 Da

IUPAC Name

(1R,17R,19R)-9,9,16,16-tetramethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0^{1,17}.0^{3,15}.0^{4,13}.0^{7,12}.0^{19,23}]hexacosa-3(15),4,6,10,12-pentaene-24,26-dione

Traditional Name

(1R,17R,19R)-9,9,16,16-tetramethyl-8-oxa-14,23,25-triazaheptacyclo[17.5.2.0^{1,17}.0^{3,15}.0^{4,13}.0^{7,12}.0^{19,23}]hexacosa-3(15),4,6,10,12-pentaene-24,26-dione

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=C(C=C1)C1=C(C=C2)C2=C(N1)C(C)(C)C1CC34CCCN3C(=O)C1(C2)NC4=O

InChI Identifier

InChI=1S/C26H29N3O3/c1-23(2)10-8-15-17(32-23)7-6-14-16-12-26-18(24(3,4)20(16)27-19(14)15)13-25(21(30)28-26)9-5-11-29(25)22(26)31/h6-8,10,18,27H,5,9,11-13H2,1-4H3,(H,28,30)

InChI Key

YCWBTRJVYADFLQ-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
Aspergillus ochraceus	NPAtlas	12465964
Aspergillus taichungensis	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Aspergillus ochraceus WC76446	KNApSAcK Database	22123792
Aspergillus sp.	KNApSAcK Database	22123792
Aspergillus versicolor NRRL35600	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloquinolines. Pyrroloquinolines are compounds containing a pyrroloquinoline moiety, which consists of a pyrrole ring fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Pyrroloquinolines

Direct Parent

Pyrroloquinolines

Alternative Parents

Substituents

Carbazole
Pyrroloquinoline
2,2-dimethyl-1-benzopyran
Isoquinolone
Alpha-amino acid or derivatives
Azaspirodecane
Benzopyran
1-benzopyran
3-alkylindole
Indolizidine
Indole or derivatives
Indole
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
Alkyl aryl ether
Piperidinone
Delta-lactam
1,4-diazinane
Benzenoid
Piperazine
Piperidine
Pyrrole
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Lactam
Secondary carboxylic acid amide
Carboxamide group
Ether
Azacycle
Oxacycle
Carboxylic acid derivative
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	3.64	ALOGPS
logP	2.89	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	10.77	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.43 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	121.86 m³·mol⁻¹	ChemAxon
Polarizability	48.54 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA010784

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8449863

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10274385

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Qian-Cutrone J, Huang S, Shu YZ, Vyas D, Fairchild C, Menendez A, Krampitz K, Dalterio R, Klohr SE, Gao Q: Stephacidin A and B: two structurally novel, selective inhibitors of the testosterone-dependent prostate LNCaP cells. J Am Chem Soc. 2002 Dec 11;124(49):14556-7. doi: 10.1021/ja028538n. [PubMed:12465964 ]

Showing NP-Card for Stephacidin A (NP0004444)

MOL for NP0004444 (Stephacidin A)

3D MOL for NP0004444 (Stephacidin A)

3D SDF for NP0004444 (Stephacidin A)

3D-SDF for NP0004444 (Stephacidin A)

PDB for NP0004444 (Stephacidin A)

3D PDB for NP0004444 (Stephacidin A)

SMILES for NP0004444 (Stephacidin A)

INCHI for NP0004444 (Stephacidin A)

Structure for NP0004444 (Stephacidin A)

3D Structure for NP0004444 (Stephacidin A)