NP-MRD: Showing NP-Card for Calicheamicin (NP0137207)

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Record Information

Version

2.0

Created at

2022-05-30 16:45:11 UTC

Updated at

2022-05-30 16:45:11 UTC

NP-MRD ID

NP0137207

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calicheamicin

Description

Calicheamicin belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Calicheamicin was first documented in 2021 (PMID: 34441852). Based on a literature review a small amount of articles have been published on Calicheamicin (PMID: 35468945) (PMID: 35290067) (PMID: 34297027) (PMID: 34155147).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305302218452D          

 84 90  0  0  0  0            999 V2000
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M  END

     RDKit          3D

158164  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652305302218452D          

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    0.6617    3.1108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1626    3.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6034    2.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    3.8741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3706    3.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8697    2.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2533    1.6170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0776    1.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4612    0.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2856    0.8207    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7263    1.5181    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5506    1.4851    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9343    0.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  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  0  0  0  0
  8  9  1  0  0  0  0
  4  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  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 34 43  1  0  0  0  0
 43 44  1  0  0  0  0
 32 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 45 48  2  0  0  0  0
 27 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 23 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 19 53  1  0  0  0  0
 16 54  1  0  0  0  0
 54 55  1  0  0  0  0
 54 56  1  0  0  0  0
 56 57  1  0  0  0  0
 13 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  3  0  0  0  0
 62 61  1  4  0  0  0
 62 63  2  0  0  0  0
 63 64  1  0  0  0  0
 64 65  3  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 66 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  2  0  0  0  0
 69 71  1  0  0  0  0
 71 72  1  0  0  0  0
 72 73  1  0  0  0  0
 73 74  2  0  0  0  0
 73 75  1  0  0  0  0
 75 76  1  0  0  0  0
 71 77  2  0  0  0  0
 59 77  1  0  0  0  0
 77 78  1  0  0  0  0
 66 78  1  0  0  0  0
 78 79  2  0  0  0  0
 79 80  1  4  0  0  0
 80 81  1  0  0  0  0
 81 82  1  0  0  0  0
 82 83  1  0  0  0  0
 83 84  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137207

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCNC1COC(CC1OC)OC1C(O)C(NOC2CC(O)C(SC(=O)C3=C(C)C(I)=C(OC4OC(C)C(O)C(OC)C4O)C(OC)=C3OC)C(C)O2)C(C)OC1OC1C#CC=CC#CC2(O)CC(=O)C(NC(=O)OC)=C1C2=CCSSSC

> <INCHI_IDENTIFIER>
InChI=1S/C55H74IN3O21S4/c1-12-57-30-24-73-35(22-34(30)68-6)78-48-43(63)40(26(3)75-53(48)77-33-17-15-13-14-16-19-55(67)23-32(61)41(58-54(66)72-10)38(33)29(55)18-20-82-84-81-11)59-80-36-21-31(60)50(28(5)74-36)83-51(65)37-25(2)39(56)46(49(71-9)45(37)69-7)79-52-44(64)47(70-8)42(62)27(4)76-52/h13-14,18,26-28,30-31,33-36,40,42-44,47-48,50,52-53,57,59-60,62-64,67H,12,20-24H2,1-11H3,(H,58,66)

> <INCHI_KEY>
HXCHCVDVKSCDHU-UHFFFAOYSA-N

> <FORMULA>
C55H74IN3O21S4

> <MOLECULAR_WEIGHT>
1368.34

> <EXACT_MASS>
1367.27424

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
158

> <JCHEM_AVERAGE_POLARIZABILITY>
133.17905171164966

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl N-{8-[(5-{[(5-{4-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoylsulfanyl}-4-hydroxy-6-methyloxan-2-yl)oxy]amino}-3-{[5-(ethylamino)-4-methoxyoxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-1-hydroxy-13-{2-[(methylsulfanyl)disulfanyl]ethylidene}-11-oxobicyclo[7.3.1]trideca-4,9-dien-2,6-diyn-10-yl}carbamate

> <JCHEM_LOGP>
4.796205527666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.12669850036554

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.418977049909197

> <JCHEM_PKA_STRONGEST_BASIC>
9.25580386617662

> <JCHEM_POLAR_SURFACE_AREA>
308.43999999999994

> <JCHEM_REFRACTIVITY>
332.63329999999985

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl N-{8-[(5-{[(5-{4-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoylsulfanyl}-4-hydroxy-6-methyloxan-2-yl)oxy]amino}-3-{[5-(ethylamino)-4-methoxyoxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-1-hydroxy-13-{2-[(methylsulfanyl)disulfanyl]ethylidene}-11-oxobicyclo[7.3.1]trideca-4,9-dien-2,6-diyn-10-yl}carbamate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAY-22         0                                  
HETATM    1  C   UNK     0      -0.593  17.893   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.123  16.529   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.700  15.227   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.016  13.864   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.555  13.802   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.271  12.439   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.448  11.137   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.090  11.199   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.806  12.562   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.345  12.624   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.061  13.987   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.164   9.774   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.703   9.712   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.526  11.014   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.810  12.378   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.065  10.953   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.887  12.254   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       8.426  12.193   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.249  13.495   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.533  14.858   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.355  16.160   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.639  17.523   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.894  16.098   0.000  0.00  0.00           C+0
HETATM   24  S   UNK     0      11.717  17.400   0.000  0.00  0.00           S+0
HETATM   25  C   UNK     0      13.256  17.339   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.972  15.975   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.078  18.641   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.362  20.004   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.824  20.065   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.185  21.306   0.000  0.00  0.00           C+0
HETATM   31  I   UNK     0      13.469  22.669   0.000  0.00  0.00           I+0
HETATM   32  C   UNK     0      15.724  21.244   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      16.546  22.546   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      18.085  22.484   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      18.801  21.121   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      20.340  21.060   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      21.056  19.696   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      21.163  22.361   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      22.702  22.300   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      20.447  23.725   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      21.269  25.027   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      20.553  26.390   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      18.908  23.786   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      18.192  25.150   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      16.440  19.881   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      17.979  19.819   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      18.695  18.456   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      15.617  18.579   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      16.333  17.216   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      15.511  15.914   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      11.610  14.735   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      13.149  14.673   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      10.788  13.433   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       6.781   9.589   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       8.320   9.528   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       5.958   8.287   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       4.419   8.349   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       3.597   7.047   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       4.313   5.684   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       5.852   5.622   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       6.568   4.259   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       5.302   3.437   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       6.941   2.037   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       5.638   0.292   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       4.100   0.353   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       3.383   1.717   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0       2.561   0.415   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0       1.845   1.778   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       1.129   3.142   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      -0.410   3.203   0.000  0.00  0.00           O+0
HETATM   71  C   UNK     0       1.951   4.443   0.000  0.00  0.00           C+0
HETATM   72  N   UNK     0       1.235   5.807   0.000  0.00  0.00           N+0
HETATM   73  C   UNK     0      -0.304   5.868   0.000  0.00  0.00           C+0
HETATM   74  O   UNK     0      -1.126   4.566   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0      -1.020   7.232   0.000  0.00  0.00           O+0
HETATM   76  C   UNK     0      -2.558   7.293   0.000  0.00  0.00           C+0
HETATM   77  C   UNK     0       3.490   4.382   0.000  0.00  0.00           C+0
HETATM   78  C   UNK     0       4.206   3.018   0.000  0.00  0.00           C+0
HETATM   79  C   UNK     0       5.745   2.957   0.000  0.00  0.00           C+0
HETATM   80  C   UNK     0       6.461   1.594   0.000  0.00  0.00           C+0
HETATM   81  S   UNK     0       8.000   1.532   0.000  0.00  0.00           S+0
HETATM   82  S   UNK     0       8.822   2.834   0.000  0.00  0.00           S+0
HETATM   83  S   UNK     0      10.361   2.772   0.000  0.00  0.00           S+0
HETATM   84  C   UNK     0      11.077   1.409   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14   57                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   54                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   53                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   51                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   48                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   45                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   43                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   34   44                                                  
CONECT   44   43                                                            
CONECT   45   32   46   48                                                  
CONECT   46   45   47                                                       
CONECT   47   46                                                            
CONECT   48   45   27   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49                                                            
CONECT   51   23   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   19                                                       
CONECT   54   16   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   57                                                       
CONECT   57   56   13   58                                                  
CONECT   58   57   59                                                       
CONECT   59   58   60   77                                                  
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67   68   78                                             
CONECT   67   66                                                            
CONECT   68   66   69                                                       
CONECT   69   68   70   71                                                  
CONECT   70   69                                                            
CONECT   71   69   72   77                                                  
CONECT   72   71   73                                                       
CONECT   73   72   74   75                                                  
CONECT   74   73                                                            
CONECT   75   73   76                                                       
CONECT   76   75                                                            
CONECT   77   71   59   78                                                  
CONECT   78   77   66   79                                                  
CONECT   79   78   80                                                       
CONECT   80   79   81                                                       
CONECT   81   80   82                                                       
CONECT   82   81   83                                                       
CONECT   83   82   84                                                       
CONECT   84   83                                                            
MASTER        0    0    0    0    0    0    0    0   84    0  180    0
END

View in JSmol

Synonyms

Value	Source
Calicheamicins	HMDB
Calicheamicin gamma(1)I	HMDB
Calichemicin gamma1	HMDB
N-{8-[(5-{[(5-{4-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoylsulfanyl}-4-hydroxy-6-methyloxan-2-yl)oxy]amino}-3-{[5-(ethylamino)-4-methoxyoxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-1-hydroxy-13-{2-[(methylsulfanyl)disulfanyl]ethylidene}-11-oxobicyclo[7.3.1]trideca-4,9-dien-2,6-diyn-10-yl}methoxycarboximidate	HMDB
N-{8-[(5-{[(5-{4-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoylsulphanyl}-4-hydroxy-6-methyloxan-2-yl)oxy]amino}-3-{[5-(ethylamino)-4-methoxyoxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-1-hydroxy-13-{2-[(methylsulphanyl)disulphanyl]ethylidene}-11-oxobicyclo[7.3.1]trideca-4,9-dien-2,6-diyn-10-yl}methoxycarboximidate	HMDB
N-{8-[(5-{[(5-{4-[(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoylsulphanyl}-4-hydroxy-6-methyloxan-2-yl)oxy]amino}-3-{[5-(ethylamino)-4-methoxyoxan-2-yl]oxy}-4-hydroxy-6-methyloxan-2-yl)oxy]-1-hydroxy-13-{2-[(methylsulphanyl)disulphanyl]ethylidene}-11-oxobicyclo[7.3.1]trideca-4,9-dien-2,6-diyn-10-yl}methoxycarboximidic acid	HMDB

Chemical Formula

C₅₅H₇₄IN₃O₂₁S₄

Average Mass

1368.3400 Da

Monoisotopic Mass

1367.27424 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCNC1COC(CC1OC)OC1C(O)C(NOC2CC(O)C(SC(=O)C3=C(C)C(I)=C(OC4OC(C)C(O)C(OC)C4O)C(OC)=C3OC)C(C)O2)C(C)OC1OC1C#CC=CC#CC2(O)CC(=O)C(NC(=O)OC)=C1C2=CCSSSC

InChI Identifier

InChI=1S/C55H74IN3O21S4/c1-12-57-30-24-73-35(22-34(30)68-6)78-48-43(63)40(26(3)75-53(48)77-33-17-15-13-14-16-19-55(67)23-32(61)41(58-54(66)72-10)38(33)29(55)18-20-82-84-81-11)59-80-36-21-31(60)50(28(5)74-36)83-51(65)37-25(2)39(56)46(49(71-9)45(37)69-7)79-52-44(64)47(70-8)42(62)27(4)76-52/h13-14,18,26-28,30-31,33-36,40,42-44,47-48,50,52-53,57,59-60,62-64,67H,12,20-24H2,1-11H3,(H,58,66)

InChI Key

HXCHCVDVKSCDHU-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Halobenzoic acid or derivatives
3-halobenzoic acid or derivatives
Dimethoxybenzene
O-dimethoxybenzene
Thiobenzoic acid or derivatives
Benzoic acid or derivatives
Anisole
Phenoxy compound
Phenol ether
Benzoyl
Methoxybenzene
Toluene
Cyclohexenone
Halobenzene
Alkyl aryl ether
Iodobenzene
Aryl halide
Aryl iodide
Monocyclic benzene moiety
Monosaccharide
Oxane
Ynone
Benzenoid
Methylcarbamate
Tertiary alcohol
Organic trisulfide
Carbamic acid ester
Ketone
Thiocarboxylic acid ester
Carbonic acid derivative
Carbothioic s-ester
Secondary alcohol
Cyclic ketone
Amino acid or derivatives
Dialkyl ether
N-organohydroxylamine
Carboxylic acid derivative
Thiocarboxylic acid or derivatives
Secondary aliphatic amine
Secondary amine
Ether
Acetal
Sulfenyl compound
Oxacycle
Organoheterocyclic compound
Organosulfur compound
Organic oxide
Organopnictogen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Amine
Organohalogen compound
Organoiodide
Organic nitrogen compound
Organonitrogen 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

External Links

HMDB ID

HMDB0249553

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3686917

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Calicheamicin

METLIN ID

Not Available

PubChem Compound

4489307

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pennesi E, Michels N, Brivio E, van der Velden VHJ, Jiang Y, Thano A, Ammerlaan AJC, Boer JM, Beverloo HB, Sleight B, Chen Y, Vormoor-Burger B, Rives S, Bielorai B, Rossig C, Petit A, Rizzari C, Engstler G, Stary J, Bautista Sirvent FJ, Chen-Santel C, Bruno B, Bertrand Y, Rialland F, Plat G, Reinhardt D, Vinti L, Von Stackelberg A, Locatelli F, Zwaan CM: Inotuzumab ozogamicin as single agent in pediatric patients with relapsed and refractory acute lymphoblastic leukemia: results from a phase II trial. Leukemia. 2022 Jun;36(6):1516-1524. doi: 10.1038/s41375-022-01576-3. Epub 2022 Apr 25. [PubMed:35468945 ]
Feng X, Liu H, Pan J, Xiong Y, Zhu X, Yan X, Duan Y, Huang Y: Liposome-Encapsulated Tiancimycin A Is Active against Melanoma and Metastatic Breast Tumors: The Effect of cRGD Modification of the Liposomal Carrier and Tiancimycin A Dose on Drug Activity and Toxicity. Mol Pharm. 2022 Apr 4;19(4):1078-1090. doi: 10.1021/acs.molpharmaceut.1c00753. Epub 2022 Mar 15. [PubMed:35290067 ]
Stokke JL, Bhojwani D: Antibody-Drug Conjugates for the Treatment of Acute Pediatric Leukemia. J Clin Med. 2021 Aug 13;10(16). pii: jcm10163556. doi: 10.3390/jcm10163556. [PubMed:34441852 ]
Mills A, Gago F: Structural and mechanistic insight into DNA bending by antitumour calicheamicins. Org Biomol Chem. 2021 Aug 5;19(30):6707-6717. doi: 10.1039/d1ob01077h. [PubMed:34297027 ]
Nicolaou KC, Rigol S, Pitsinos EN, Das D, Lu Y, Rout S, Schammel AW, Holte D, Lin B, Gu C, Sarvaiya H, Trinidad J, Barbour N, Valdiosera AM, Sandoval J, Lee C, Aujay M, Fernando H, Dhar A, Karsunky H, Taylor N, Pysz M, Gavrilyuk J: Uncialamycin-based antibody-drug conjugates: Unique enediyne ADCs exhibiting bystander killing effect. Proc Natl Acad Sci U S A. 2021 Jun 22;118(25). pii: 2107042118. doi: 10.1073/pnas.2107042118. [PubMed:34155147 ]

Showing NP-Card for Calicheamicin (NP0137207)

MOL for NP0137207 (Calicheamicin)

3D MOL for NP0137207 (Calicheamicin)

3D SDF for NP0137207 (Calicheamicin)

3D-SDF for NP0137207 (Calicheamicin)

PDB for NP0137207 (Calicheamicin)

3D PDB for NP0137207 (Calicheamicin)

SMILES for NP0137207 (Calicheamicin)

INCHI for NP0137207 (Calicheamicin)

Structure for NP0137207 (Calicheamicin)

3D Structure for NP0137207 (Calicheamicin)