NP-MRD: Showing NP-Card for Cytochalasin B2 (NP0043861)

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Record Information

Version

1.0

Created at

2021-06-22 17:26:19 UTC

Updated at

2021-06-22 17:26:19 UTC

NP-MRD ID

NP0043861

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cytochalasin B2

Description

CHEMBL2018715 belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Cytochalasin B2 is found in Pyrenophora dematioidea and Phoma sp.. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on CHEMBL2018715 (PMID: 22483395) (PMID: 27466641) (PMID: 27253005) (PMID: 26389468).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222119262D          

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NP0043861
     RDKit          3D

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M  END


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 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
  3 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043861

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CCC[C@@H](O)\C=C\C(=O)O[C@]23[C@H]([C@H](CC4=CC=CC=C4)NC2=O)C(C)=C(C)[C@@H](O)[C@@H]3\C=C\C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H37NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18,22-24,26-27,31,33H,7,9-10,13,17H2,1-3H3,(H,30,34)/b14-8+,16-15+/t18-,22-,23+,24+,26+,27-,29-/m1/s1

> <INCHI_KEY>
SEJHGGVKMSZDDH-ZQLHMVIYSA-N

> <FORMULA>
C29H37NO5

> <MOLECULAR_WEIGHT>
479.617

> <EXACT_MASS>
479.267173295

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.606725888051855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,9R,13S,15aS,16S,18aS,18bS)-16-benzyl-5,13-dihydroxy-9,14,15-trimethyl-2H,5H,6H,7H,8H,9H,10H,13H,15aH,16H,17H,18H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,18-dione

> <ALOGPS_LOGP>
3.45

> <JCHEM_LOGP>
3.980765348333333

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.139474977451908

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.921766303733367

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8716125209274397

> <JCHEM_POLAR_SURFACE_AREA>
95.85999999999999

> <JCHEM_REFRACTIVITY>
137.22289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,9R,13S,15aS,16S,18aS,18bS)-16-benzyl-5,13-dihydroxy-9,14,15-trimethyl-5H,6H,7H,8H,9H,10H,13H,15aH,16H,17H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043861
     RDKit          3D

 72 75  0  0  0  0  0  0  0  0999 V2000
   -2.6668    1.6352   -3.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529    0.8412   -2.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512    0.7232   -1.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6178    1.4531   -0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6863   -0.0551   -0.1218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5498   -1.2629    0.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1269   -1.3979    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0057   -0.3574    1.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5652    0.7108    2.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3766    1.7151    3.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7128    1.6689    2.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2078    0.6176    2.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3814   -0.3787    1.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6901   -2.3969   -0.1654 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5527   -1.9426   -0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745   -2.6524   -1.6954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2935   -0.5378   -0.4521 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5526   -0.4944    0.6786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826   -1.3106    1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2767   -0.9068    2.9376 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2468   -2.6546    1.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4340   -3.0563    1.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3472   -2.0436    0.8060 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1382   -2.7492   -0.0951 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1422   -1.2880    1.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0419    0.2012    1.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6288    0.4568    0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3556    1.7883   -0.4084 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2711    2.0086   -1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    1.7021   -0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6911    0.5666   -1.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539   -0.0105   -2.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2183    0.3018   -1.5705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7061    0.1429   -2.7911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1279    0.8137   -3.8748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7573    1.3863   -3.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6044    2.7250   -3.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2056    1.5336   -4.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4225    0.7081   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438    1.9899    0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746    2.2319   -1.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6422    0.6068    0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981   -1.3556   -0.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6496   -2.4003    1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2854   -1.5188    2.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5140    0.7898    2.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9753    2.5490    3.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4047    2.4483    3.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2812    0.6267    1.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7686   -1.1887    1.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9477   -3.3679    0.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -3.4537    2.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7762   -4.0794    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6717   -1.3210    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4153   -3.5850    0.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2266   -1.5350    1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7618   -1.5596    2.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5001    0.7949    2.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643    0.4541    1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263   -0.2765   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7358    0.4171    0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804    2.5759    0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7041    2.6274   -2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1889    2.5040   -1.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5192    1.0116   -2.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245    1.5582   -0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6695    2.6619   -1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6246    0.2199   -2.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5944   -0.8552   -2.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    1.3760   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -0.8982   -3.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885    1.7470   -3.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  1
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34  2  1  0
 17  5  1  0
 13  8  1  0
 33 17  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  1
  6 43  1  6
  7 44  1  0
  7 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 14 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  6
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  1
 29 63  1  0
 29 64  1  0
 29 65  1  0
 30 66  1  0
 30 67  1  0
 31 68  1  0
 32 69  1  0
 33 70  1  1
 34 71  1  6
 35 72  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0       3.709  -4.704   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.189  -4.277   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.559  -2.782   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.038  -2.355   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.711  -0.970   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       9.236  -1.181   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.502  -2.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.148  -3.423   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.628  -2.996   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.778  -4.918   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.298  -5.345   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.929  -6.840   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.888  -5.986   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.367  -5.558   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.477  -6.626   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.957  -6.199   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.066  -7.267   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.327  -4.704   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.806  -4.277   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.176  -2.782   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.066  -1.714   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.436  -0.219   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.587  -2.142   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.477  -1.074   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.997  -1.501   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.888  -0.433   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.892  -3.370   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.986   0.389   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.799   1.696   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.074   3.055   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.888   4.362   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.427   4.311   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.152   2.953   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.338   1.645   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.449  -1.714   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    4    9   10                                             
CONECT    9    8   25                                                       
CONECT   10    8   11   13                                                  
CONECT   11   10    2   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    9   26                                                  
CONECT   26   25                                                            
CONECT   27    7                                                            
CONECT   28    5   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35    3                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

COMPND    NP0043861
HETATM    1  C1  UNL     1      -2.667   1.635  -3.443  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.953   0.841  -2.411  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.351   0.723  -1.172  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.618   1.453  -0.803  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.686  -0.055  -0.122  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.550  -1.263   0.134  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.127  -1.398   1.481  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.006  -0.357   1.978  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.565   0.711   2.726  1.00  0.00           C  
HETATM   10  C10 UNL     1      -4.377   1.715   3.207  1.00  0.00           C  
HETATM   11  C11 UNL     1      -5.713   1.669   2.935  1.00  0.00           C  
HETATM   12  C12 UNL     1      -6.208   0.618   2.188  1.00  0.00           C  
HETATM   13  C13 UNL     1      -5.381  -0.379   1.715  1.00  0.00           C  
HETATM   14  N1  UNL     1      -1.690  -2.397  -0.165  1.00  0.00           N  
HETATM   15  C14 UNL     1      -0.553  -1.943  -0.874  1.00  0.00           C  
HETATM   16  O1  UNL     1       0.074  -2.652  -1.695  1.00  0.00           O  
HETATM   17  C15 UNL     1      -0.293  -0.538  -0.452  1.00  0.00           C  
HETATM   18  O2  UNL     1       0.553  -0.494   0.679  1.00  0.00           O  
HETATM   19  C16 UNL     1       0.683  -1.311   1.757  1.00  0.00           C  
HETATM   20  O3  UNL     1       0.277  -0.907   2.938  1.00  0.00           O  
HETATM   21  C17 UNL     1       1.247  -2.655   1.780  1.00  0.00           C  
HETATM   22  C18 UNL     1       2.434  -3.056   1.370  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.347  -2.044   0.806  1.00  0.00           C  
HETATM   24  O4  UNL     1       4.138  -2.749  -0.095  1.00  0.00           O  
HETATM   25  C20 UNL     1       4.142  -1.288   1.820  1.00  0.00           C  
HETATM   26  C21 UNL     1       4.042   0.201   1.554  1.00  0.00           C  
HETATM   27  C22 UNL     1       4.629   0.457   0.217  1.00  0.00           C  
HETATM   28  C23 UNL     1       4.356   1.788  -0.408  1.00  0.00           C  
HETATM   29  C24 UNL     1       5.271   2.009  -1.593  1.00  0.00           C  
HETATM   30  C25 UNL     1       2.908   1.702  -0.871  1.00  0.00           C  
HETATM   31  C26 UNL     1       2.691   0.567  -1.809  1.00  0.00           C  
HETATM   32  C27 UNL     1       1.554  -0.010  -2.090  1.00  0.00           C  
HETATM   33  C28 UNL     1       0.218   0.302  -1.571  1.00  0.00           C  
HETATM   34  C29 UNL     1      -0.706   0.143  -2.791  1.00  0.00           C  
HETATM   35  O5  UNL     1      -0.128   0.814  -3.875  1.00  0.00           O  
HETATM   36  H1  UNL     1      -3.757   1.386  -3.437  1.00  0.00           H  
HETATM   37  H2  UNL     1      -2.604   2.725  -3.171  1.00  0.00           H  
HETATM   38  H3  UNL     1      -2.206   1.534  -4.423  1.00  0.00           H  
HETATM   39  H4  UNL     1      -4.422   0.708  -0.785  1.00  0.00           H  
HETATM   40  H5  UNL     1      -3.544   1.990   0.138  1.00  0.00           H  
HETATM   41  H6  UNL     1      -3.875   2.232  -1.574  1.00  0.00           H  
HETATM   42  H7  UNL     1      -1.642   0.607   0.790  1.00  0.00           H  
HETATM   43  H8  UNL     1      -3.398  -1.356  -0.607  1.00  0.00           H  
HETATM   44  H9  UNL     1      -3.650  -2.400   1.543  1.00  0.00           H  
HETATM   45  H10 UNL     1      -2.285  -1.519   2.222  1.00  0.00           H  
HETATM   46  H11 UNL     1      -2.514   0.790   2.975  1.00  0.00           H  
HETATM   47  H12 UNL     1      -3.975   2.549   3.801  1.00  0.00           H  
HETATM   48  H13 UNL     1      -6.405   2.448   3.297  1.00  0.00           H  
HETATM   49  H14 UNL     1      -7.281   0.627   1.999  1.00  0.00           H  
HETATM   50  H15 UNL     1      -5.769  -1.189   1.138  1.00  0.00           H  
HETATM   51  H16 UNL     1      -1.948  -3.368   0.134  1.00  0.00           H  
HETATM   52  H17 UNL     1       0.606  -3.454   2.197  1.00  0.00           H  
HETATM   53  H18 UNL     1       2.776  -4.079   1.426  1.00  0.00           H  
HETATM   54  H19 UNL     1       2.672  -1.321   0.305  1.00  0.00           H  
HETATM   55  H20 UNL     1       4.415  -3.585   0.367  1.00  0.00           H  
HETATM   56  H21 UNL     1       5.227  -1.535   1.757  1.00  0.00           H  
HETATM   57  H22 UNL     1       3.762  -1.560   2.837  1.00  0.00           H  
HETATM   58  H23 UNL     1       4.500   0.795   2.371  1.00  0.00           H  
HETATM   59  H24 UNL     1       2.964   0.454   1.536  1.00  0.00           H  
HETATM   60  H25 UNL     1       4.226  -0.276  -0.475  1.00  0.00           H  
HETATM   61  H26 UNL     1       5.736   0.417   0.334  1.00  0.00           H  
HETATM   62  H27 UNL     1       4.480   2.576   0.362  1.00  0.00           H  
HETATM   63  H28 UNL     1       4.704   2.627  -2.318  1.00  0.00           H  
HETATM   64  H29 UNL     1       6.189   2.504  -1.217  1.00  0.00           H  
HETATM   65  H30 UNL     1       5.519   1.012  -2.008  1.00  0.00           H  
HETATM   66  H31 UNL     1       2.225   1.558  -0.016  1.00  0.00           H  
HETATM   67  H32 UNL     1       2.670   2.662  -1.386  1.00  0.00           H  
HETATM   68  H33 UNL     1       3.625   0.220  -2.302  1.00  0.00           H  
HETATM   69  H34 UNL     1       1.594  -0.855  -2.813  1.00  0.00           H  
HETATM   70  H35 UNL     1       0.144   1.376  -1.298  1.00  0.00           H  
HETATM   71  H36 UNL     1      -0.839  -0.898  -3.075  1.00  0.00           H  
HETATM   72  H37 UNL     1       0.088   1.747  -3.669  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3    3   34
CONECT    3    4    5
CONECT    4   39   40   41
CONECT    5    6   17   42
CONECT    6    7   14   43
CONECT    7    8   44   45
CONECT    8    9    9   13
CONECT    9   10   46
CONECT   10   11   11   47
CONECT   11   12   48
CONECT   12   13   13   49
CONECT   13   50
CONECT   14   15   51
CONECT   15   16   16   17
CONECT   17   18   33
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   22   52
CONECT   22   23   53
CONECT   23   24   25   54
CONECT   24   55
CONECT   25   26   56   57
CONECT   26   27   58   59
CONECT   27   28   60   61
CONECT   28   29   30   62
CONECT   29   63   64   65
CONECT   30   31   66   67
CONECT   31   32   32   68
CONECT   32   33   69
CONECT   33   34   70
CONECT   34   35   71
CONECT   35   72
END

NP0043861
     RDKit          3D

72 75  0  0  0  0  0  0  0  0999 V2000
   -2.6668    1.6352   -3.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9529    0.8412   -2.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3512    0.7232   -1.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6178    1.4531   -0.8026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6863   -0.0551   -0.1218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5498   -1.2629    0.1343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1269   -1.3979    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0057   -0.3574    1.9781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5652    0.7108    2.7262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3766    1.7151    3.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7128    1.6689    2.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2078    0.6176    2.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3814   -0.3787    1.7152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6901   -2.3969   -0.1654 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5527   -1.9426   -0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745   -2.6524   -1.6954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2935   -0.5378   -0.4521 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5526   -0.4944    0.6786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6826   -1.3106    1.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2767   -0.9068    2.9376 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2468   -2.6546    1.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4340   -3.0563    1.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3472   -2.0436    0.8060 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1382   -2.7492   -0.0951 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1422   -1.2880    1.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0419    0.2012    1.5536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6288    0.4568    0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3556    1.7883   -0.4084 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2711    2.0086   -1.5932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9083    1.7021   -0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6911    0.5666   -1.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539   -0.0105   -2.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2183    0.3018   -1.5705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7061    0.1429   -2.7911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1279    0.8137   -3.8748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7573    1.3863   -3.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6044    2.7250   -3.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2056    1.5336   -4.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4225    0.7081   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5438    1.9899    0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746    2.2319   -1.5744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6422    0.6068    0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981   -1.3556   -0.6066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6496   -2.4003    1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2854   -1.5188    2.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5140    0.7898    2.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9753    2.5490    3.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4047    2.4483    3.2969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2812    0.6267    1.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7686   -1.1887    1.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9477   -3.3679    0.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -3.4537    2.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7762   -4.0794    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6717   -1.3210    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4153   -3.5850    0.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2266   -1.5350    1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7618   -1.5596    2.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5001    0.7949    2.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643    0.4541    1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263   -0.2765   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7358    0.4171    0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4804    2.5759    0.3625 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7041    2.6274   -2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1889    2.5040   -1.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5192    1.0116   -2.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245    1.5582   -0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6695    2.6619   -1.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6246    0.2199   -2.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5944   -0.8552   -2.8134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    1.3760   -1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391   -0.8982   -3.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885    1.7470   -3.6687 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  1
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34  2  1  0
 17  5  1  0
 13  8  1  0
 33 17  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  4 40  1  0
  4 41  1  0
  5 42  1  1
  6 43  1  6
  7 44  1  0
  7 45  1  0
  9 46  1  0
 10 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 14 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  6
 24 55  1  0
 25 56  1  0
 25 57  1  0
 26 58  1  0
 26 59  1  0
 27 60  1  0
 27 61  1  0
 28 62  1  1
 29 63  1  0
 29 64  1  0
 29 65  1  0
 30 66  1  0
 30 67  1  0
 31 68  1  0
 32 69  1  0
 33 70  1  1
 34 71  1  6
 35 72  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₇NO₅

Average Mass

479.6170 Da

Monoisotopic Mass

479.26717 Da

IUPAC Name

(5R,9R,13S,15aS,16S,18aS,18bS)-16-benzyl-5,13-dihydroxy-9,14,15-trimethyl-2H,5H,6H,7H,8H,9H,10H,13H,15aH,16H,17H,18H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,18-dione

Traditional Name

(5R,9R,13S,15aS,16S,18aS,18bS)-16-benzyl-5,13-dihydroxy-9,14,15-trimethyl-5H,6H,7H,8H,9H,10H,13H,15aH,16H,17H,18bH-oxacyclotetradeca[3,2-e]isoindole-2,18-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1CCC[C@@H](O)\C=C\C(=O)O[C@]23[C@H]([C@H](CC4=CC=CC=C4)NC2=O)C(C)=C(C)[C@@H](O)[C@@H]3\C=C\C1

InChI Identifier

InChI=1S/C29H37NO5/c1-18-9-7-13-22(31)15-16-25(32)35-29-23(14-8-10-18)27(33)20(3)19(2)26(29)24(30-28(29)34)17-21-11-5-4-6-12-21/h4-6,8,11-12,14-16,18,22-24,26-27,31,33H,7,9-10,13,17H2,1-3H3,(H,30,34)/b14-8+,16-15+/t18-,22-,23+,24+,26+,27-,29-/m1/s1

InChI Key

SEJHGGVKMSZDDH-ZQLHMVIYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, 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
Helminthosporium dematioideum	LOTUS Database	35616633
Phoma sp.	Linigton's dataset	22483395

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
Isoindole
Monocyclic benzene moiety
Pyrrolidone
2-pyrrolidone
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrolidine
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Lactone
Oxacycle
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen 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	3.45	ALOGPS
logP	3.98	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	12.92	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.86 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	137.22 m³·mol⁻¹	ChemAxon
Polarizability	53.61 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28499612

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60150677

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim EL, Li JL, Dang HT, Hong J, Lee CO, Kim DK, Yoon WD, Kim E, Liu Y, Jung JH: Cytotoxic cytochalasins from the endozoic fungus Phoma sp. of the giant jellyfish Nemopilema nomurai. Bioorg Med Chem Lett. 2012 May 1;22(9):3126-9. doi: 10.1016/j.bmcl.2012.03.058. Epub 2012 Mar 20. [PubMed:22483395 ]
Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Stomach (Gastric) Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389468 ]

Showing NP-Card for Cytochalasin B2 (NP0043861)

MOL for NP0043861 (Cytochalasin B2)

3D MOL for NP0043861 (Cytochalasin B2)

3D SDF for NP0043861 (Cytochalasin B2)

3D-SDF for NP0043861 (Cytochalasin B2)

PDB for NP0043861 (Cytochalasin B2)

3D PDB for NP0043861 (Cytochalasin B2)

SMILES for NP0043861 (Cytochalasin B2)

INCHI for NP0043861 (Cytochalasin B2)

Structure for NP0043861 (Cytochalasin B2)

3D Structure for NP0043861 (Cytochalasin B2)