NP-MRD: Showing NP-Card for 2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate (NP0220021)

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Record Information

Version

2.0

Created at

2022-09-05 21:12:54 UTC

Updated at

2022-09-05 21:12:54 UTC

NP-MRD ID

NP0220021

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate

Description

Haterumalide B belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate was first documented in 2009 (PMID: 19344140). Based on a literature review very few articles have been published on Haterumalide B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223122D          

 38 39  0  0  1  0            999 V2000
    5.8451    5.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8451    5.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1306    4.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162    5.0049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017    4.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017    3.7674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9872    5.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727    4.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727    3.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5583    5.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438    4.5924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8438    3.7674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293    5.0049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6243    4.6694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2623    5.2442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0828    5.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4183    6.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334    6.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1129    6.6653    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690    7.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841    8.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9636    8.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4787    8.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8142    9.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418    8.6676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8267    9.3351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4912   10.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9761   10.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3293   10.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774    7.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1925    7.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280    7.3328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5280    6.4928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    5.8254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7774    5.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5596    4.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2740    5.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5596    3.7674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 11  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  1  1  0  0  0
 15 35  1  6  0  0  0
  2 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
M  END


  Mrv1652309052223122D          

 38 39  0  0  1  0            999 V2000
    5.8451    5.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8451    5.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1306    4.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162    5.0049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017    4.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017    3.7674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9872    5.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727    4.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2727    3.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5583    5.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438    4.5924    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8438    3.7674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293    5.0049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6243    4.6694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2623    5.2442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0828    5.3304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4183    6.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9334    6.7516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1129    6.6653    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.2690    7.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7841    8.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9636    8.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4787    8.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8142    9.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3418    8.6676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8267    9.3351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4912   10.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9761   10.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3293   10.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6774    7.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1925    7.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280    7.3328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5280    6.4928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    5.8254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7774    5.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5596    4.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2740    5.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5596    3.7674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 11  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  1  1  0  0  0
 15 35  1  6  0  0  0
  2 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0220021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1CC(=O)O[C@@H]2C[C@@H](CC\C(Cl)=C\C\C=C1/C)O[C@@H]2[C@H](O)\C=C(/C)CC(=O)OCC(=C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H37ClO9/c1-16(12-26(33)35-15-18(3)19(4)30)11-23(32)28-25-13-22(37-28)10-9-21(29)8-6-7-17(2)24(36-20(5)31)14-27(34)38-25/h7-8,11,22-25,28,32H,3,6,9-10,12-15H2,1-2,4-5H3/b16-11+,17-7+,21-8-/t22-,23-,24-,25-,28-/m1/s1

> <INCHI_KEY>
BJBNPXLMBSHSQN-VUEPVXMWSA-N

> <FORMULA>
C28H37ClO9

> <MOLECULAR_WEIGHT>
553.05

> <EXACT_MASS>
552.2126105

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.716043821038944

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylidene-3-oxobutyl (3E,5R)-5-[(1R,5R,6E,9Z,13R,15R)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate

> <JCHEM_LOGP>
2.7459491789999984

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.61609904494066

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.733546770541079

> <JCHEM_PKA_STRONGEST_BASIC>
-3.352746393615596

> <JCHEM_POLAR_SURFACE_AREA>
125.43

> <JCHEM_REFRACTIVITY>
142.19319999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-methylidene-3-oxobutyl (3E,5R)-5-[(1R,5R,6E,9Z,13R,15R)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      10.911  10.883   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.911   9.343   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.577   8.573   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.243   9.343   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.910   8.573   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.910   7.033   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.576   9.343   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.242   8.573   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.242   7.033   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.909   9.343   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.575   8.573   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.575   7.033   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.241   9.343   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.165   8.716   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.356   9.789   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.888   9.950   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.514  11.357   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.609  12.603   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0      -2.077  12.442   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0      -4.235  14.010   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.330  15.256   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.799  15.095   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.893  16.341   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.520  17.747   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.638  16.180   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.543  17.425   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.917  18.832   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.822  20.078   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.615  18.993   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.264  14.773   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.359  13.527   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.172  13.688   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.986  12.120   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.080  10.874   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.451  11.035   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.245   8.573   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.578   9.343   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.245   7.033   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   34                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   35                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   13   35                                                  
CONECT   35   34   15                                                       
CONECT   36    2   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₇ClO₉

Average Mass

553.0500 Da

Monoisotopic Mass

552.21261 Da

IUPAC Name

2-methylidene-3-oxobutyl (3E,5R)-5-[(1R,5R,6E,9Z,13R,15R)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate

Traditional Name

2-methylidene-3-oxobutyl (3E,5R)-5-[(1R,5R,6E,9Z,13R,15R)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1CC(=O)O[C@@H]2C[C@@H](CC\C(Cl)=C\C\C=C1/C)O[C@@H]2[C@H](O)\C=C(/C)CC(=O)OCC(=C)C(C)=O

InChI Identifier

InChI=1S/C28H37ClO9/c1-16(12-26(33)35-15-18(3)19(4)30)11-23(32)28-25-13-22(37-28)10-9-21(29)8-6-7-17(2)24(36-20(5)31)14-27(34)38-25/h7-8,11,22-25,28,32H,3,6,9-10,12-15H2,1-2,4-5H3/b16-11+,17-7+,21-8-/t22-,23-,24-,25-,28-/m1/s1

InChI Key

BJBNPXLMBSHSQN-VUEPVXMWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Monosaccharide
Alpha,beta-unsaturated ketone
Tetrahydrofuran
Enone
Acryloyl-group
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.75	ChemAxon
pKa (Strongest Acidic)	13.73	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	142.19 m³·mol⁻¹	ChemAxon
Polarizability	56.72 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100936918

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ueda M, Yamaura M, Ikeda Y, Suzuki Y, Yoshizato K, Hayakawa I, Kigoshi H: Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues. J Org Chem. 2009 May 1;74(9):3370-7. doi: 10.1021/jo802806z. [PubMed:19344140 ]
LOTUS database [Link]

Showing NP-Card for 2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate (NP0220021)

MOL for NP0220021 (2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

3D MOL for NP0220021 (2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

3D SDF for NP0220021 (2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

3D-SDF for NP0220021 (2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

PDB for NP0220021 (2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

3D PDB for NP0220021 (2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

SMILES for NP0220021 (2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

INCHI for NP0220021 (2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

Structure for NP0220021 (2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)

3D Structure for NP0220021 (2-methylidene-3-oxobutyl (3e,5r)-5-[(1r,5r,6e,9z,13r,15r)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoate)