NP-MRD: Showing NP-Card for UCN-02 (NP0014894)

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Record Information

Version

1.0

Created at

2021-01-05 23:56:12 UTC

Updated at

2021-07-15 17:18:29 UTC

NP-MRD ID

NP0014894

Secondary Accession Numbers

None

Natural Product Identification

Common Name

UCN-02

Provided By

NPAtlas

Description

7-Hydroxystaurosporine is also known as UCN 01 or UCN-02. UCN-02 is found in Streptomyces and Streptomyces longisporoflavus. It was first documented in 1989 (PMID: 2656615). Based on a literature review very few articles have been published on 7-Hydroxystaurosporine (PMID: 32140897) (PMID: 33037137) (PMID: 30942626) (PMID: 30840849).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242120073D          

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  Mrv1652306242120073D          

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    4.3640    2.9419    1.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285    2.9513   -0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0355    0.4532   -0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2666    1.2177   -1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060    1.2374    0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859    2.7521    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071    2.6857   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6979   -1.7099   -2.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7700   -0.5206   -3.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9129   -1.9751   -3.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3409   -1.2016   -0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0968   -1.5027    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6772   -1.9042    2.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958   -2.6967    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6625   -2.5803    2.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 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
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
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 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 21 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
  9  3  1  0  0  0  0
 31 12  1  0  0  0  0
 29  5  1  0  0  0  0
 18 13  1  0  0  0  0
 31 19  1  0  0  0  0
 35 20  1  0  0  0  0
 30 22  1  0  0  0  0
 28 23  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  2 40  1  0  0  0  0
  3 41  1  6  0  0  0
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  5 44  1  6  0  0  0
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  9 48  1  6  0  0  0
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 34 60  1  0  0  0  0
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 36 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0014894

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])N([H])C(=O)C2=C3C4=C([H])C([H])=C([H])C([H])=C4N4C3=C3N(C5=C([H])C([H])=C([H])C([H])=C5C3=C12)[C@]1(O[C@]4([H])C([H])([H])[C@@]([H])(N([H])C([H])([H])[H])[C@@]1([H])OC([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H26N4O4/c1-28-25(35-3)15(29-2)12-18(36-28)31-16-10-6-4-8-13(16)19-21-22(27(34)30-26(21)33)20-14-9-5-7-11-17(14)32(28)24(20)23(19)31/h4-11,15,18,25,27,29,34H,12H2,1-3H3,(H,30,33)/t15-,18-,25-,27-,28+/m1/s1

> <INCHI_KEY>
PBCZSGKMGDDXIJ-HQCWYSJUSA-N

> <FORMULA>
C28H26N4O4

> <MOLECULAR_WEIGHT>
482.5304

> <EXACT_MASS>
482.19540534

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
52.256565257885825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,6R,18R)-18-hydroxy-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^{2,6}.0^{7,28}.0^{8,13}.0^{15,19}.0^{20,27}.0^{21,26}]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
3.6054492226666657

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.158875593219094

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.68456181260914

> <JCHEM_PKA_STRONGEST_BASIC>
9.553297938543723

> <JCHEM_POLAR_SURFACE_AREA>
89.68

> <JCHEM_REFRACTIVITY>
133.402

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,6R,18R)-18-hydroxy-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^{2,6}.0^{7,28}.0^{8,13}.0^{15,19}.0^{20,27}.0^{21,26}]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 69  0  0  0  0  0  0  0  0999 V2000
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    5.0355    0.4532   -0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
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 29 30  1  0
 30 31  2  0
 21 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
  9  3  1  0
 31 12  1  0
 29  5  1  0
 18 13  1  0
 31 19  1  0
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 30 22  1  0
 28 23  1  0
  1 37  1  0
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 34 60  1  0
 35 61  1  6
 36 62  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       4.650   2.402   0.192  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.240   1.011   0.219  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.103   0.877  -0.643  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.979   1.746  -0.057  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.899   1.738  -1.118  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.966   0.700  -1.974  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.325  -0.549  -1.478  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.695  -1.306  -2.761  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.523  -0.544  -0.593  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.218  -0.760   0.749  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.026  -1.750   1.318  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.163  -1.172  -0.827  0.00  0.00           N+0
HETATM   13  C   UNK     0      -0.042  -2.508  -0.719  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.731  -3.573  -1.092  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.255  -4.850  -0.837  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.955  -5.085  -0.228  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.737  -4.011   0.151  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.266  -2.745  -0.101  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.804  -1.514   0.174  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.971  -1.068   0.773  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.255   0.285   0.926  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.340   1.218   0.469  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.276   2.597   0.475  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.101   3.577   0.917  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.713   4.915   0.761  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.517   5.232   0.171  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.686   4.229  -0.274  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.071   2.920  -0.119  0.00  0.00           C+0
HETATM   29  N   UNK     0      -0.420   1.829  -0.476  0.00  0.00           N+0
HETATM   30  C   UNK     0      -1.175   0.779  -0.129  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.918  -0.576  -0.274  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.556   0.422   1.547  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.225   1.433   1.881  0.00  0.00           O+0
HETATM   34  N   UNK     0      -5.044  -0.914   1.757  0.00  0.00           N+0
HETATM   35  C   UNK     0      -4.060  -1.872   1.369  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.639  -2.497   2.555  0.00  0.00           O+0
HETATM   37  H   UNK     0       5.763   2.491   0.087  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.364   2.942   1.111  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.229   2.951  -0.688  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.035   0.453  -0.144  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.267   1.218  -1.670  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.606   1.237   0.861  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.386   2.752   0.155  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.007   2.686  -1.686  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.698  -1.710  -2.630  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.770  -0.521  -3.580  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.913  -1.975  -3.117  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.341  -1.202  -0.939  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.097  -1.503   1.281  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.677  -1.904   2.363  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.796  -2.697   0.780  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.713  -3.447  -1.559  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.890  -5.664  -1.144  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.329  -6.064  -0.027  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.692  -4.123   0.626  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.029   3.353   1.377  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.408   5.657   1.130  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.221   6.286   0.053  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.268   4.466  -0.745  0.00  0.00           H+0
HETATM   60  H   UNK     0      -5.990  -1.171   2.141  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.494  -2.551   0.638  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.663  -2.580   2.624  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    1    3   40                                                  
CONECT    3    2    4    9   41                                             
CONECT    4    3    5   42   43                                             
CONECT    5    4    6   29   44                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9   12                                             
CONECT    8    7   45   46   47                                             
CONECT    9    7   10    3   48                                             
CONECT   10    9   11                                                       
CONECT   11   10   49   50   51                                             
CONECT   12    7   13   31                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   52                                                  
CONECT   15   14   16   53                                                  
CONECT   16   15   17   54                                                  
CONECT   17   16   18   55                                                  
CONECT   18   17   19   13                                                  
CONECT   19   18   20   31                                                  
CONECT   20   19   21   35                                                  
CONECT   21   20   22   32                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25   56                                                  
CONECT   25   24   26   57                                                  
CONECT   26   25   27   58                                                  
CONECT   27   26   28   59                                                  
CONECT   28   27   29   23                                                  
CONECT   29   28   30    5                                                  
CONECT   30   29   31   22                                                  
CONECT   31   30   12   19                                                  
CONECT   32   21   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   60                                                  
CONECT   35   34   36   20   61                                             
CONECT   36   35   62                                                       
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    2                                                            
CONECT   41    3                                                            
CONECT   42    4                                                            
CONECT   43    4                                                            
CONECT   44    5                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47    8                                                            
CONECT   48    9                                                            
CONECT   49   11                                                            
CONECT   50   11                                                            
CONECT   51   11                                                            
CONECT   52   14                                                            
CONECT   53   15                                                            
CONECT   54   16                                                            
CONECT   55   17                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   26                                                            
CONECT   59   27                                                            
CONECT   60   34                                                            
CONECT   61   35                                                            
CONECT   62   36                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  138    0
END

RDKit          3D

62 69  0  0  0  0  0  0  0  0999 V2000
    4.6499    2.4024    0.1923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2401    1.0111    0.2187 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028    0.8768   -0.6425 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9792    1.7462   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8992    1.7383   -1.1182 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9656    0.7000   -1.9741 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3251   -0.5490   -1.4782 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6952   -1.3061   -2.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5231   -0.5444   -0.5928 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2180   -0.7601    0.7485 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0265   -1.7497    1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1628   -1.1717   -0.8269 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0423   -2.5079   -0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7311   -3.5726   -1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2554   -4.8497   -0.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9550   -5.0849   -0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7366   -4.0114    0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2657   -2.7455   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8040   -1.5142    0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9707   -1.0679    0.7731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2545    0.2854    0.9263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3402    1.2182    0.4692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2758    2.5966    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1007    3.5769    0.9165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7127    4.9154    0.7606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173    5.2324    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6863    4.2293   -0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0711    2.9204   -0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204    1.8291   -0.4758 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    0.7790   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9175   -0.5758   -0.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5556    0.4215    1.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2249    1.4334    1.8808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0440   -0.9144    1.7574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0596   -1.8717    1.3690 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6385   -2.4969    2.5547 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7635    2.4906    0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640    2.9419    1.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2285    2.9513   -0.6882 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0355    0.4532   -0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2666    1.2177   -1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6060    1.2374    0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859    2.7521    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0071    2.6857   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6979   -1.7099   -2.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7700   -0.5206   -3.5802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9129   -1.9751   -3.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3409   -1.2016   -0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0968   -1.5027    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6772   -1.9042    2.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958   -2.6967    0.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7129   -3.4471   -1.5588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8896   -5.6643   -1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3288   -6.0643   -0.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6918   -4.1226    0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0292    3.3534    1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4077    5.6567    1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2206    6.2859    0.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2677    4.4660   -0.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9902   -1.1705    2.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4936   -2.5505    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625   -2.5803    2.6237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
  7 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
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 21 32  1  0
 32 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
  9  3  1  0
 31 12  1  0
 29  5  1  0
 18 13  1  0
 31 19  1  0
 35 20  1  0
 30 22  1  0
 28 23  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  2 40  1  0
  3 41  1  6
  4 42  1  0
  4 43  1  0
  5 44  1  6
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  6
 11 49  1  0
 11 50  1  0
 11 51  1  0
 14 52  1  0
 15 53  1  0
 16 54  1  0
 17 55  1  0
 24 56  1  0
 25 57  1  0
 26 58  1  0
 27 59  1  0
 34 60  1  0
 35 61  1  6
 36 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
7-Epi-hydroxystaurosporine	MeSH
7-Hydroxy-staurosporine	MeSH
UCN 01	MeSH
UCN 02	MeSH
UCN-01	MeSH
UCN-02	MeSH

Chemical Formula

C₂₈H₂₆N₄O₄

Average Mass

482.5304 Da

Monoisotopic Mass

482.19541 Da

IUPAC Name

(2S,3R,4R,6R,18R)-18-hydroxy-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^{2,6}.0^{7,28}.0^{8,13}.0^{15,19}.0^{20,27}.0^{21,26}]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-16-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CN[C@@H]1C[C@H]2O[C@@](C)([C@@H]1OC)N1C3=CC=CC=C3C3=C4[C@@H](O)NC(=O)C4=C4C5=CC=CC=C5N2C4=C13

InChI Identifier

InChI=1S/C28H26N4O4/c1-28-25(35-3)15(29-2)12-18(36-28)31-16-10-6-4-8-13(16)19-21-22(27(34)30-26(21)33)20-14-9-5-7-11-17(14)32(28)24(20)23(19)31/h4-11,15,18,25,27,29,34H,12H2,1-3H3,(H,30,33)/t15-,18-,25-,27-,28+/m1/s1

InChI Key

PBCZSGKMGDDXIJ-HQCWYSJUSA-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
Streptomyces	NPAtlas	2656615
Streptomyces longisporoflavus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces sp.	KNApSAcK Database	22123792
Streptomyces sp. N-126	KNApSAcK Database	22123792
Streptomyces sp. N-71	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Indolocarbazoles

Alternative Parents

Substituents

Indolocarbazole
Pyrrolo[2,3-a]carbazole
Pyrroloindole
Isoindolone
Indole
Isoindoline
Isoindole or derivatives
Benzenoid
Oxane
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Lactam
Alkanolamine
Carboxylic acid derivative
Dialkyl ether
Secondary aliphatic amine
Ether
Oxacycle
Azacycle
Secondary amine
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
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	2.42	ALOGPS
logP	3.61	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.68	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	89.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	133.4 m³·mol⁻¹	ChemAxon
Polarizability	52.26 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA020738

HMDB ID

Not Available

DrugBank ID

DB01933

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024753

Chemspider ID

65225

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72271

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Takahashi I, Saitoh Y, Yoshida M, Sano H, Nakano H, Morimoto M, Tamaoki T: UCN-01 and UCN-02, new selective inhibitors of protein kinase C. II. Purification, physico-chemical properties, structural determination and biological activities. J Antibiot (Tokyo). 1989 Apr;42(4):571-6. doi: 10.7164/antibiotics.42.571. [PubMed:2656615 ]
Abdulridha MK, Al-Marzoqi AH, Al-Awsi GRL, Mubarak SMH, Heidarifard M, Ghasemian A: Anticancer Effects of Herbal Medicine Compounds and Novel Formulations: a Literature Review. J Gastrointest Cancer. 2020 Sep;51(3):765-773. doi: 10.1007/s12029-020-00385-0. [PubMed:32140897 ]
Huang Z, Kondoh E, Visco ZR, Baba T, Matsumura N, Dolan E, Whitaker RS, Konishi I, Fujii S, Berchuck A, Murphy SK: Targeting Dormant Ovarian Cancer Cells In Vitro and in an In Vivo Mouse Model of Platinum Resistance. Mol Cancer Ther. 2021 Jan;20(1):85-95. doi: 10.1158/1535-7163.MCT-20-0119. Epub 2020 Oct 9. [PubMed:33037137 ]
Jain A, Jain R, Jain S, Khatik R, Veer Kohli D: Minicapsules encapsulating nanoparticles for targeting, apoptosis induction and treatment of colon cancer. Artif Cells Nanomed Biotechnol. 2019 Dec;47(1):1085-1093. doi: 10.1080/21691401.2019.1593848. [PubMed:30942626 ]
Liang C, Ding M, Weng XQ, Sheng Y, Wu J, Cai X: The combination of UCN-01 and ATRA triggers differentiation in ATRA resistant acute promyelocytic leukemia cell lines via RAF-1 independent activation of MEK/ERK. Food Chem Toxicol. 2019 Apr;126:303-312. doi: 10.1016/j.fct.2019.02.033. Epub 2019 Mar 3. [PubMed:30840849 ]

Showing NP-Card for UCN-02 (NP0014894)

MOL for NP0014894 (UCN-02)

3D MOL for NP0014894 (UCN-02)

3D SDF for NP0014894 (UCN-02)

3D-SDF for NP0014894 (UCN-02)

PDB for NP0014894 (UCN-02)

3D PDB for NP0014894 (UCN-02)

SMILES for NP0014894 (UCN-02)

INCHI for NP0014894 (UCN-02)

Structure for NP0014894 (UCN-02)

3D Structure for NP0014894 (UCN-02)