NP-MRD: Showing NP-Card for Phomaketide B (NP0015959)

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Record Information

Version

2.0

Created at

2021-01-06 01:04:27 UTC

Updated at

2021-07-15 17:21:24 UTC

NP-MRD ID

NP0015959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phomaketide B

Provided By

NPAtlas

Description

Phomaketide B is found in Phoma sp. NTOU4195. Based on a literature review very few articles have been published on (1S,2R,3R,4S)-4-(chloromethyl)-4-hydroxy-2-methoxy-3-[(2R,3S)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl (2E)-3-[(2R,3R)-3-methyloxiran-2-yl]prop-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117253D          

 62 64  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242117253D          

 62 64  0  0  0  0            999 V2000
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    7.5329    1.8393   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4397    4.1741   -1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8478    4.1667    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2328    3.1131   -0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0380   -2.9310    1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -3.5536   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0241   -4.4376    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3282   -2.9061    2.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4739    3.7942    2.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7334    1.9646   -0.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0301    3.3673    0.3716 H   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  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  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  1  0  0  0  0
 26 27  2  3  0  0  0
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 20  3  1  0  0  0  0
 24 21  1  0  0  0  0
 12 10  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 33  1  6  0  0  0
  4 34  1  6  0  0  0
  8 35  1  0  0  0  0
  9 36  1  0  0  0  0
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 28 57  1  0  0  0  0
 28 58  1  0  0  0  0
 28 59  1  0  0  0  0
 29 60  1  0  0  0  0
 29 61  1  0  0  0  0
 29 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0015959

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1(C([H])([H])Cl)C([H])([H])C([H])([H])[C@]([H])(OC(=O)C(\[H])=C(/[H])[C@@]2([H])O[C@]2([H])C([H])([H])[H])[C@]([H])(OC([H])([H])[H])[C@@]1([H])[C@]1(O[C@@]1([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H33ClO6/c1-13(2)6-8-17-21(4,29-17)20-19(26-5)16(10-11-22(20,25)12-23)28-18(24)9-7-15-14(3)27-15/h6-7,9,14-17,19-20,25H,8,10-12H2,1-5H3/b9-7+/t14-,15-,16+,17+,19+,20+,21+,22-/m1/s1

> <INCHI_KEY>
HVVQOFBOWDNQCO-PIPZUTLJSA-N

> <FORMULA>
C22H33ClO6

> <MOLECULAR_WEIGHT>
428.95

> <EXACT_MASS>
428.1965665

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.11441750678768

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,3R,4S)-4-(chloromethyl)-4-hydroxy-2-methoxy-3-[(2R,3S)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl (2E)-3-[(2R,3R)-3-methyloxiran-2-yl]prop-2-enoate

> <ALOGPS_LOGP>
3.86

> <JCHEM_LOGP>
3.287565385000001

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.621652684970414

> <JCHEM_PKA_STRONGEST_BASIC>
-3.401689115593941

> <JCHEM_POLAR_SURFACE_AREA>
80.82000000000001

> <JCHEM_REFRACTIVITY>
110.9839

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,4S)-4-(chloromethyl)-4-hydroxy-2-methoxy-3-[(2R,3S)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl (2E)-3-[(2R,3R)-3-methyloxiran-2-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
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  1  2  1  0
  2  3  1  0
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  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
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  4 14  1  0
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 18 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  3
 27 28  1  0
 27 29  1  0
 20  3  1  0
 24 21  1  0
 12 10  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  6
  4 34  1  6
  8 35  1  0
  9 36  1  0
 10 37  1  1
 12 38  1  6
 13 39  1  0
 13 40  1  0
 13 41  1  0
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 20 49  1  1
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 26 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.085   1.433   0.945  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.102   0.099   1.266  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.234  -0.759   0.175  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.111  -1.426   0.014  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.139  -0.608   0.522  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.098  -0.049  -0.249  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.050  -0.283  -1.459  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.176   0.807   0.270  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.082   1.321  -0.543  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.159   2.183   0.017  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.312   1.492   0.417  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.336   2.413  -0.749  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.275   3.559  -0.419  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.165  -2.838   0.488  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.061  -3.342   1.126  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.242  -3.070   0.182  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.948  -3.665  -1.012  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.399  -3.766   0.897  0.00  0.00           C+0
HETATM   19 Cl   UNK     0      -2.567  -2.995   2.487  0.00  0.00          Cl+0
HETATM   20  C   UNK     0      -1.444  -1.594   0.165  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.342  -1.227  -1.021  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.679  -1.351  -2.400  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.539  -2.083  -1.067  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.661  -0.716  -0.949  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.475  -0.256   0.195  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.835   0.895   0.886  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.411   2.083   0.965  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.756   3.211   1.656  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.741   2.281   0.347  0.00  0.00           C+0
HETATM   30  H   UNK     0       0.787   1.694   0.269  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.129   2.119   1.777  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.959   1.634   0.288  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.349  -0.034  -0.693  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.323  -1.454  -1.073  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.204   1.001   1.333  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.016   1.100  -1.599  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.803   2.922   0.765  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.533   1.839  -1.667  0.00  0.00           H+0
HETATM   39  H   UNK     0       8.440   4.174  -1.328  0.00  0.00           H+0
HETATM   40  H   UNK     0       7.848   4.167   0.384  0.00  0.00           H+0
HETATM   41  H   UNK     0       9.233   3.113  -0.062  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.038  -2.931   1.206  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.433  -3.554  -0.318  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.024  -4.438   1.270  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.328  -2.906   2.098  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.202  -3.216  -1.451  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.011  -4.802   1.098  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.306  -3.864   0.330  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.122  -1.396   1.052  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.630  -1.067  -2.406  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.876  -2.309  -2.891  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.196  -0.584  -3.053  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.041  -0.242  -1.926  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.555  -1.065   0.957  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.511  -0.001  -0.123  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.876   0.791   1.355  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.905   2.866   2.307  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.321   3.899   0.899  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.474   3.794   2.271  0.00  0.00           H+0
HETATM   60  H   UNK     0      -6.506   1.670   0.876  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.733   1.965  -0.718  0.00  0.00           H+0
HETATM   62  H   UNK     0      -6.030   3.367   0.372  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   20   33                                             
CONECT    4    3    5   14   34                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   35                                                  
CONECT    9    8   10   36                                                  
CONECT   10    9   11   12   37                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   10   38                                             
CONECT   13   12   39   40   41                                             
CONECT   14    4   15   42   43                                             
CONECT   15   14   16   44   45                                             
CONECT   16   15   17   18   20                                             
CONECT   17   16   46                                                       
CONECT   18   16   19   47   48                                             
CONECT   19   18                                                            
CONECT   20   16   21    3   49                                             
CONECT   21   20   22   23   24                                             
CONECT   22   21   50   51   52                                             
CONECT   23   21   24                                                       
CONECT   24   23   25   21   53                                             
CONECT   25   24   26   54   55                                             
CONECT   26   25   27   56                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   57   58   59                                             
CONECT   29   27   60   61   62                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37   10                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   13                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   17                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   20                                                            
CONECT   50   22                                                            
CONECT   51   22                                                            
CONECT   52   22                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
CONECT   56   26                                                            
CONECT   57   28                                                            
CONECT   58   28                                                            
CONECT   59   28                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
CONECT   62   29                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  128    0
END

RDKit          3D

62 64  0  0  0  0  0  0  0  0999 V2000
   -0.0850    1.4326    0.9449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1023    0.0989    1.2660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2337   -0.7593    0.1747 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1115   -1.4261    0.0135 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1392   -0.6079    0.5221 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0977   -0.0494   -0.2491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0497   -0.2826   -1.4593 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1759    0.8067    0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0824    1.3212   -0.5429 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1586    2.1826    0.0172 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3122    1.4922    0.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3358    2.4134   -0.7493 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2752    3.5586   -0.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1646   -2.8383    0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613   -3.3422    1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2423   -3.0695    0.1815 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9481   -3.6652   -1.0123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3987   -3.7661    0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5671   -2.9951    2.4873 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.4442   -1.5942    0.1648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3423   -1.2273   -1.0211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6787   -1.3513   -2.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5393   -2.0834   -1.0669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6613   -0.7161   -0.9494 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4751   -0.2562    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8348    0.8954    0.8856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4107    2.0835    0.9653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556    3.2106    1.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7406    2.2813    0.3465 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7866    1.6943    0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1289    2.1194    1.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    1.6336    0.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3487   -0.0342   -0.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3231   -1.4536   -1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2038    1.0013    1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0157    1.0998   -1.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8029    2.9220    0.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5329    1.8393   -1.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4397    4.1741   -1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8478    4.1667    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2328    3.1131   -0.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0380   -2.9310    1.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -3.5536   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0241   -4.4376    1.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3282   -2.9061    2.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2023   -3.2164   -1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0108   -4.8024    1.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3059   -3.8635    0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1224   -1.3964    1.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6300   -1.0673   -2.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8758   -2.3085   -2.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1955   -0.5842   -3.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0414   -0.2421   -1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5548   -1.0649    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5112   -0.0014   -0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763    0.7910    1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9052    2.8659    2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213    3.8994    0.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4739    3.7942    2.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5065    1.6703    0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7334    1.9646   -0.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0301    3.3673    0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  3
 27 28  1  0
 27 29  1  0
 20  3  1  0
 24 21  1  0
 12 10  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  6
  4 34  1  6
  8 35  1  0
  9 36  1  0
 10 37  1  1
 12 38  1  6
 13 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 20 49  1  1
 22 50  1  0
 22 51  1  0
 22 52  1  0
 24 53  1  6
 25 54  1  0
 25 55  1  0
 26 56  1  0
 28 57  1  0
 28 58  1  0
 28 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1S,2R,3R,4S)-4-(Chloromethyl)-4-hydroxy-2-methoxy-3-[(2R,3S)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl (2E)-3-[(2R,3R)-3-methyloxiran-2-yl]prop-2-enoic acid	Generator

Chemical Formula

C₂₂H₃₃ClO₆

Average Mass

428.9500 Da

Monoisotopic Mass

428.19657 Da

IUPAC Name

(1S,2R,3R,4S)-4-(chloromethyl)-4-hydroxy-2-methoxy-3-[(2R,3S)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl (2E)-3-[(2R,3R)-3-methyloxiran-2-yl]prop-2-enoate

Traditional Name

(1S,2R,3R,4S)-4-(chloromethyl)-4-hydroxy-2-methoxy-3-[(2R,3S)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]cyclohexyl (2E)-3-[(2R,3R)-3-methyloxiran-2-yl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](CC[C@@](O)(CCl)[C@@H]1[C@@]1(C)O[C@H]1CC=C(C)C)OC(=O)\C=C\[C@H]1O[C@@H]1C

InChI Identifier

InChI=1S/C22H33ClO6/c1-13(2)6-8-17-21(4,29-17)20-19(26-5)16(10-11-22(20,25)12-23)28-18(24)9-7-15-14(3)27-15/h6-7,9,14-17,19-20,25H,8,10-12H2,1-5H3/b9-7+/t14-,15-,16+,17+,19+,20+,21+,22-/m1/s1

InChI Key

HVVQOFBOWDNQCO-PIPZUTLJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phoma sp. NTOU4195	NPAtlas	27976895

Chemical Taxonomy

Classification

Not classified

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	3.86	ALOGPS
logP	3.29	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.82 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	110.98 m³·mol⁻¹	ChemAxon
Polarizability	46.11 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA022098

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

60596843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132526607

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Phomaketide B (NP0015959)

MOL for NP0015959 (Phomaketide B)

3D MOL for NP0015959 (Phomaketide B)

3D SDF for NP0015959 (Phomaketide B)

3D-SDF for NP0015959 (Phomaketide B)

PDB for NP0015959 (Phomaketide B)

3D PDB for NP0015959 (Phomaketide B)

SMILES for NP0015959 (Phomaketide B)

INCHI for NP0015959 (Phomaketide B)

Structure for NP0015959 (Phomaketide B)

3D Structure for NP0015959 (Phomaketide B)