NP-MRD: Showing NP-Card for Phomopsichalasin G (NP0043952)

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Record Information

Version

1.0

Created at

2021-06-22 17:42:29 UTC

Updated at

2021-06-22 17:42:30 UTC

NP-MRD ID

NP0043952

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phomopsichalasin G

Description

(3R,4R,6R,6aS,10R,12R,15S,15aS,15bS)-3-[(2-hydroxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-1,6,15-triol belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole. Phomopsichalasin G is found in Phomopsis sp. Xy21. It was first documented in 2016 (Luo, et al.). Based on a literature review very few articles have been published on (3R,4R,6R,6aS,10R,12R,15S,15aS,15bS)-3-[(2-hydroxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindole-1,6,15-triol.

Structure

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


  Mrv1652306222119422D          

 33 36  0  0  1  0            999 V2000
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M  END

NP0043952
     RDKit          3D

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M  END


  Mrv1652306222119422D          

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M  END
> <DATABASE_ID>
NP0043952

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2[C@@H](CC3=CC=CC=C3O)NC(=O)[C@]22[C@H](\C=C\C[C@@H](C)C[C@@H](C)\C=C\[C@@H]2O)[C@@H](O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H37NO4/c1-16-8-7-10-21-26(32)19(4)18(3)25-22(15-20-9-5-6-11-23(20)30)29-27(33)28(21,25)24(31)13-12-17(2)14-16/h5-7,9-13,16-18,21-22,24-26,30-32H,4,8,14-15H2,1-3H3,(H,29,33)/b10-7+,13-12+/t16-,17+,18+,21-,22-,24+,25-,26+,28+/m1/s1

> <INCHI_KEY>
GPYFHLIYZCGNSD-YJZFUNBLSA-N

> <FORMULA>
C28H37NO4

> <MOLECULAR_WEIGHT>
451.607

> <EXACT_MASS>
451.272258675

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
33.80193676701104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R,6R,6aS,10R,12R,15S,15aS,15bS)-6,15-dihydroxy-3-[(2-hydroxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-1-one

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
3.863211772000001

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.787768866027434

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.355629457366357

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3330853268085535

> <JCHEM_POLAR_SURFACE_AREA>
89.79

> <JCHEM_REFRACTIVITY>
132.18200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,6R,6aS,10R,12R,15S,15aS,15bS)-6,15-dihydroxy-3-[(2-hydroxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-2H,3H,4H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

NP0043952
     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
    1.0188   -4.7305   -0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6624   -3.4997   -0.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036   -2.5101   -1.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9942   -3.0814   -1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999   -1.2179   -0.6811 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4571   -1.1874    0.5426 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7390   -0.4574    0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    0.9609    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    1.3356   -1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911    2.6422   -1.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6519    3.6456   -0.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4465    3.3264    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4805    1.9982    0.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684    1.7605    2.2915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5799   -0.8014    1.6068 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343   -1.1853    1.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341   -1.6988    2.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -0.8298   -0.2129 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0813    0.6766   -0.4766 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7669    0.9339   -1.5625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1783    1.4804    0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2627    2.1447    1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5194    2.2633    0.2947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5741    3.7094   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7116    2.0668    1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677    0.7230    0.9909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2398    0.4598    2.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3414   -0.3837    0.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1641   -0.7941   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625   -1.2406   -1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7713   -1.5750   -1.0606 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7252   -3.0563   -0.6662 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6501   -3.7321   -1.4651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3427   -5.4995   -0.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0306   -5.0497   -0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4151   -2.2842   -2.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114   -2.3525   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574   -3.9149   -2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3517   -3.5420   -0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0079   -0.4578   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7263   -2.2789    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2579   -0.5473    1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849   -0.9727   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123    0.5243   -1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552    2.8831   -2.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191    4.7053   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2557    4.1342    1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0949    2.5141    2.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -0.3488    2.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0609    1.0770   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374    0.8015   -2.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674    1.5273    1.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721    2.7064    2.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632    1.6145   -0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996    3.9197   -0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778    3.7925   -0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7129    4.4125    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4684    2.8423    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3612    2.1327    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9931    0.7772    0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2689    1.3156    2.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8062   -0.3932    2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2669    0.1926    1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7362   -1.2332    1.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256   -0.0650    1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1432   -0.6679   -1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4410   -1.4594   -2.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792   -1.5346   -2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545   -3.2349    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560   -4.1820   -0.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  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
 13 14  1  0
  6 15  1  0
 15 16  1  0
 16 17  2  0
 18 16  1  1
 18 19  1  0
 19 20  1  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
 26 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32  2  1  0
 18  5  1  0
 13  8  1  0
 31 18  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  6
  4 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  6
  6 41  1  1
  7 42  1  0
  7 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 14 48  1  0
 15 49  1  0
 19 50  1  6
 20 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  6
 24 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  6
 27 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
 31 68  1  6
 32 69  1  1
 33 70  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       1.766  -9.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.109  -7.674   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.944  -6.666   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.520  -7.324   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.235  -5.153   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.306  -3.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.313  -4.033   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.029  -2.637   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.567  -2.561   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.271  -1.191   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.436   0.103   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.898   0.027   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.194  -1.343   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.344  -1.419   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       1.187  -2.662   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       2.465  -3.014   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.612  -2.001   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.690  -4.649   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.981  -3.137   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.338  -1.409   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.548  -2.516   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.292  -1.168   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.804  -1.459   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.975  -0.285   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.995  -2.987   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.220  -4.144   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.803  -3.710   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.929  -5.657   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.474  -6.161   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.310  -5.153   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.855  -5.657   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.564  -7.169   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.349  -8.617   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    6   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    5   19   31                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   18   32                                                  
CONECT   32   31    2   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

COMPND    NP0043952
HETATM    1  C1  UNL     1       1.019  -4.730  -0.686  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.662  -3.500  -0.922  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.604  -2.510  -1.439  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.994  -3.081  -1.459  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.600  -1.218  -0.681  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.457  -1.187   0.543  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.739  -0.457   0.444  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.716   0.961   0.088  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.922   1.336  -1.251  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.891   2.642  -1.673  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.652   3.646  -0.780  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.446   3.326   0.532  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.480   1.998   0.951  1.00  0.00           C  
HETATM   14  O1  UNL     1       3.268   1.761   2.291  1.00  0.00           O  
HETATM   15  N1  UNL     1       1.580  -0.801   1.607  1.00  0.00           N  
HETATM   16  C14 UNL     1       0.234  -1.185   1.201  1.00  0.00           C  
HETATM   17  O2  UNL     1      -0.534  -1.699   2.051  1.00  0.00           O  
HETATM   18  C15 UNL     1       0.160  -0.830  -0.213  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.081   0.677  -0.477  1.00  0.00           C  
HETATM   20  O3  UNL     1      -0.767   0.934  -1.563  1.00  0.00           O  
HETATM   21  C17 UNL     1      -0.178   1.480   0.717  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.263   2.145   1.043  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.519   2.263   0.295  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.574   3.709  -0.221  1.00  0.00           C  
HETATM   25  C21 UNL     1      -3.712   2.067   1.204  1.00  0.00           C  
HETATM   26  C22 UNL     1      -4.368   0.723   0.991  1.00  0.00           C  
HETATM   27  C23 UNL     1      -5.240   0.460   2.198  1.00  0.00           C  
HETATM   28  C24 UNL     1      -3.341  -0.384   0.827  1.00  0.00           C  
HETATM   29  C25 UNL     1      -3.164  -0.794  -0.586  1.00  0.00           C  
HETATM   30  C26 UNL     1      -2.163  -1.241  -1.252  1.00  0.00           C  
HETATM   31  C27 UNL     1      -0.771  -1.575  -1.061  1.00  0.00           C  
HETATM   32  C28 UNL     1      -0.725  -3.056  -0.666  1.00  0.00           C  
HETATM   33  O4  UNL     1      -1.650  -3.732  -1.465  1.00  0.00           O  
HETATM   34  H1  UNL     1       0.343  -5.500  -0.299  1.00  0.00           H  
HETATM   35  H2  UNL     1       2.031  -5.050  -0.868  1.00  0.00           H  
HETATM   36  H3  UNL     1       1.415  -2.284  -2.546  1.00  0.00           H  
HETATM   37  H4  UNL     1       3.711  -2.352  -1.934  1.00  0.00           H  
HETATM   38  H5  UNL     1       2.957  -3.915  -2.236  1.00  0.00           H  
HETATM   39  H6  UNL     1       3.352  -3.542  -0.553  1.00  0.00           H  
HETATM   40  H7  UNL     1       2.008  -0.458  -1.371  1.00  0.00           H  
HETATM   41  H8  UNL     1       2.726  -2.279   0.830  1.00  0.00           H  
HETATM   42  H9  UNL     1       4.258  -0.547   1.466  1.00  0.00           H  
HETATM   43  H10 UNL     1       4.485  -0.973  -0.220  1.00  0.00           H  
HETATM   44  H11 UNL     1       4.112   0.524  -1.945  1.00  0.00           H  
HETATM   45  H12 UNL     1       4.055   2.883  -2.712  1.00  0.00           H  
HETATM   46  H13 UNL     1       3.619   4.705  -1.082  1.00  0.00           H  
HETATM   47  H14 UNL     1       3.256   4.134   1.241  1.00  0.00           H  
HETATM   48  H15 UNL     1       3.095   2.514   2.932  1.00  0.00           H  
HETATM   49  H16 UNL     1       1.774  -0.349   2.538  1.00  0.00           H  
HETATM   50  H17 UNL     1       1.061   1.077  -0.884  1.00  0.00           H  
HETATM   51  H18 UNL     1      -0.337   0.801  -2.429  1.00  0.00           H  
HETATM   52  H19 UNL     1       0.667   1.527   1.441  1.00  0.00           H  
HETATM   53  H20 UNL     1      -1.272   2.706   2.009  1.00  0.00           H  
HETATM   54  H21 UNL     1      -2.663   1.614  -0.558  1.00  0.00           H  
HETATM   55  H22 UNL     1      -1.600   3.920  -0.706  1.00  0.00           H  
HETATM   56  H23 UNL     1      -3.378   3.792  -0.968  1.00  0.00           H  
HETATM   57  H24 UNL     1      -2.713   4.412   0.613  1.00  0.00           H  
HETATM   58  H25 UNL     1      -4.468   2.842   0.994  1.00  0.00           H  
HETATM   59  H26 UNL     1      -3.361   2.133   2.249  1.00  0.00           H  
HETATM   60  H27 UNL     1      -4.993   0.777   0.086  1.00  0.00           H  
HETATM   61  H28 UNL     1      -5.269   1.316   2.903  1.00  0.00           H  
HETATM   62  H29 UNL     1      -4.806  -0.393   2.797  1.00  0.00           H  
HETATM   63  H30 UNL     1      -6.267   0.193   1.955  1.00  0.00           H  
HETATM   64  H31 UNL     1      -3.736  -1.233   1.462  1.00  0.00           H  
HETATM   65  H32 UNL     1      -2.426  -0.065   1.340  1.00  0.00           H  
HETATM   66  H33 UNL     1      -4.143  -0.668  -1.141  1.00  0.00           H  
HETATM   67  H34 UNL     1      -2.441  -1.459  -2.344  1.00  0.00           H  
HETATM   68  H35 UNL     1      -0.279  -1.535  -2.100  1.00  0.00           H  
HETATM   69  H36 UNL     1      -0.955  -3.235   0.381  1.00  0.00           H  
HETATM   70  H37 UNL     1      -2.356  -4.182  -0.931  1.00  0.00           H  
CONECT    1    2    2   34   35
CONECT    2    3   32
CONECT    3    4    5   36
CONECT    4   37   38   39
CONECT    5    6   18   40
CONECT    6    7   15   41
CONECT    7    8   42   43
CONECT    8    9    9   13
CONECT    9   10   44
CONECT   10   11   11   45
CONECT   11   12   46
CONECT   12   13   13   47
CONECT   13   14
CONECT   14   48
CONECT   15   16   49
CONECT   16   17   17   18
CONECT   18   19   31
CONECT   19   20   21   50
CONECT   20   51
CONECT   21   22   22   52
CONECT   22   23   53
CONECT   23   24   25   54
CONECT   24   55   56   57
CONECT   25   26   58   59
CONECT   26   27   28   60
CONECT   27   61   62   63
CONECT   28   29   64   65
CONECT   29   30   30   66
CONECT   30   31   67
CONECT   31   32   68
CONECT   32   33   69
CONECT   33   70
END

NP0043952
     RDKit          3D

70 73  0  0  0  0  0  0  0  0999 V2000
    1.0188   -4.7305   -0.6861 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6624   -3.4997   -0.9221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036   -2.5101   -1.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9942   -3.0814   -1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999   -1.2179   -0.6811 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4571   -1.1874    0.5426 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7390   -0.4574    0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    0.9609    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9222    1.3356   -1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911    2.6422   -1.6731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6519    3.6456   -0.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4465    3.3264    0.5322 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4805    1.9982    0.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684    1.7605    2.2915 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5799   -0.8014    1.6068 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343   -1.1853    1.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5341   -1.6988    2.0510 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -0.8298   -0.2129 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0813    0.6766   -0.4766 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7669    0.9339   -1.5625 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1783    1.4804    0.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2627    2.1447    1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5194    2.2633    0.2947 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5741    3.7094   -0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7116    2.0668    1.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3677    0.7230    0.9909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2398    0.4598    2.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3414   -0.3837    0.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1641   -0.7941   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625   -1.2406   -1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7713   -1.5750   -1.0606 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7252   -3.0563   -0.6662 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6501   -3.7321   -1.4651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3427   -5.4995   -0.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0306   -5.0497   -0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4151   -2.2842   -2.5461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114   -2.3525   -1.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574   -3.9149   -2.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3517   -3.5420   -0.5528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0079   -0.4578   -1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7263   -2.2789    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2579   -0.5473    1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849   -0.9727   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123    0.5243   -1.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552    2.8831   -2.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191    4.7053   -1.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2557    4.1342    1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0949    2.5141    2.9317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7736   -0.3488    2.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0609    1.0770   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3374    0.8015   -2.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674    1.5273    1.4412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721    2.7064    2.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6632    1.6145   -0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5996    3.9197   -0.7060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778    3.7925   -0.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7129    4.4125    0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4684    2.8423    0.9943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3612    2.1327    2.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9931    0.7772    0.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2689    1.3156    2.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8062   -0.3932    2.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2669    0.1926    1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7362   -1.2332    1.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256   -0.0650    1.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1432   -0.6679   -1.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4410   -1.4594   -2.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2792   -1.5346   -2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9545   -3.2349    0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560   -4.1820   -0.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  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
 13 14  1  0
  6 15  1  0
 15 16  1  0
 16 17  2  0
 18 16  1  1
 18 19  1  0
 19 20  1  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
 26 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 32  2  1  0
 18  5  1  0
 13  8  1  0
 31 18  1  0
  1 34  1  0
  1 35  1  0
  3 36  1  6
  4 37  1  0
  4 38  1  0
  4 39  1  0
  5 40  1  6
  6 41  1  1
  7 42  1  0
  7 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 12 47  1  0
 14 48  1  0
 15 49  1  0
 19 50  1  6
 20 51  1  0
 21 52  1  0
 22 53  1  0
 23 54  1  6
 24 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  6
 27 61  1  0
 27 62  1  0
 27 63  1  0
 28 64  1  0
 28 65  1  0
 29 66  1  0
 30 67  1  0
 31 68  1  6
 32 69  1  1
 33 70  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₇NO₄

Average Mass

451.6070 Da

Monoisotopic Mass

451.27226 Da

IUPAC Name

(3R,4R,6R,6aS,10R,12R,15S,15aS,15bS)-6,15-dihydroxy-3-[(2-hydroxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-1H,2H,3H,4H,5H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-1-one

Traditional Name

(3R,4R,6R,6aS,10R,12R,15S,15aS,15bS)-6,15-dihydroxy-3-[(2-hydroxyphenyl)methyl]-4,10,12-trimethyl-5-methylidene-2H,3H,4H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-1-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2[C@@H](CC3=CC=CC=C3O)NC(=O)[C@]22[C@H](\C=C\C[C@@H](C)C[C@@H](C)\C=C\[C@@H]2O)[C@@H](O)C1=C

InChI Identifier

InChI=1S/C28H37NO4/c1-16-8-7-10-21-26(32)19(4)18(3)25-22(15-20-9-5-6-11-23(20)30)29-27(33)28(21,25)24(31)13-12-17(2)14-16/h5-7,9-13,16-18,21-22,24-26,30-32H,4,8,14-15H2,1-3H3,(H,29,33)/b10-7+,13-12+/t16-,17+,18+,21-,22-,24+,25-,26+,28+/m1/s1

InChI Key

GPYFHLIYZCGNSD-YJZFUNBLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, 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
Phomopsis sp. Xy21	Linigton's dataset	Yan-Fang Luo, Min Zhang, Jun-Gui Dai, Patchara Pedpradab, Wen-Jing Wang, Jun Wu. Cytochalasins fr...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindoles

Direct Parent

Isoindoles

Alternative Parents

Substituents

Isoindole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Cyclic carboximidic acid
Pyrroline
Cyclic alcohol
Secondary alcohol
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
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	4.06	ALOGPS
logP	3.86	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.36	ChemAxon
pKa (Strongest Basic)	-0.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.79 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.18 m³·mol⁻¹	ChemAxon
Polarizability	33.8 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

78442071

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586986

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yan-Fang Luo, Min Zhang, Jun-Gui Dai, Patchara Pedpradab, Wen-Jing Wang, Jun Wu (2016). Yan-Fang Luo, Min Zhang, Jun-Gui Dai, Patchara Pedpradab, Wen-Jing Wang, Jun Wu. Cytochalasins from mangrove endophytic fungi Phomopsis spp. xy21 and xy22 Phytochemistry Letters Volume 17, September 2016, Pages 162-166 DOI: 10.1016/j.phytol.2016.07.027. Phytochemistry Letters.

Showing NP-Card for Phomopsichalasin G (NP0043952)

MOL for NP0043952 (Phomopsichalasin G)

3D MOL for NP0043952 (Phomopsichalasin G)

3D SDF for NP0043952 (Phomopsichalasin G)

3D-SDF for NP0043952 (Phomopsichalasin G)

PDB for NP0043952 (Phomopsichalasin G)

3D PDB for NP0043952 (Phomopsichalasin G)

SMILES for NP0043952 (Phomopsichalasin G)

INCHI for NP0043952 (Phomopsichalasin G)

Structure for NP0043952 (Phomopsichalasin G)

3D Structure for NP0043952 (Phomopsichalasin G)