NP-MRD: Showing NP-Card for methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate (NP0243844)

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Record Information

Version

2.0

Created at

2022-09-07 04:28:59 UTC

Updated at

2022-09-07 04:28:59 UTC

NP-MRD ID

NP0243844

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate

Description

Punaglandin 3 epoxide belongs to the class of organic compounds known as clavulones and derivatives. These are ester derivatives of prostanoids. methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate is found in Carijoa riisei. Based on a literature review very few articles have been published on Punaglandin 3 epoxide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206292D          

 35 36  0  0  1  0            999 V2000
   -0.7418    6.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5213    6.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1450    6.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9245    6.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5481    6.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3922    5.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0159    4.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8600    3.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4836    3.4414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9556    4.1180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8813    2.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0712    3.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5311    2.4099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8011    1.6303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2610    1.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509    1.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5311    0.2271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209    2.5658    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1808    1.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3707    2.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1694    1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795    1.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2496    2.4099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5196    1.0067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3297    1.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4509    3.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9910    3.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8011    3.8131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209    4.7485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2313    2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8327    1.4082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0500    2.2326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2371    1.4291    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.8296    2.5027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2059    3.0427    0.0000 C   0  0  2  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  2  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
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 11 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 35 34  1  6  0  0  0
 32 35  1  0  0  0  0
  9 35  1  0  0  0  0
M  END

     RDKit          3D

 68 69  0  0  0  0  0  0  0  0999 V2000
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    0.4825    0.1319    1.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5631   -0.5177    0.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9691   -0.2196    1.2917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5426   -1.4929    1.5075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7271   -2.0134    2.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3265   -3.3478    3.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3618   -1.3043    3.7551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6738    0.7215    0.4333 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9737    1.2436    0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0094    0.2122    1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4025   -0.6227   -0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9785    0.0893   -1.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2543   -0.5393   -2.2317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2344    1.4407   -1.0778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8000    2.1092   -2.2087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9320    0.2911   -0.8891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4352    0.8465   -2.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6834    1.8292   -1.8508 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5455    1.1824    2.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4157    1.9513    2.4719 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8995    1.1658    2.8706 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0535    0.6930    4.5552 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    2.7639    0.4088    1.9117 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4048   -1.8398    0.7053 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3918   -3.1340   -0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6163   -3.1495   -0.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1955   -2.0408   -2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7714   -1.5190   -1.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6545    0.2973   -0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6997   -0.1923   -2.5288 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4265    2.0987   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8526    2.3980   -2.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9487    2.7085   -0.5835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9328   -0.2509   -1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4115    0.5760   -1.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9434    1.8850   -0.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9959   -1.5701   -0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4079   -1.2625    0.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8433    0.2103    2.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4345   -3.2644    3.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9109   -3.7747    3.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
  9 35  1  0
 35 34  1  0
 34 32  1  0
 32 33  1  1
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 30 11  1  0
 11 12  2  0
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 13 14  1  0
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 27 29  2  0
 11  9  1  0
 32 35  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
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 28 65  1  0
 28 66  1  0
 28 67  1  0
M  END


  Mrv1652309072206292D          

 35 36  0  0  1  0            999 V2000
   -0.7418    6.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5213    6.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6  7  2  0  0  0  0
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 35 34  1  6  0  0  0
 32 35  1  0  0  0  0
  9 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243844

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H33ClO9/c1-5-6-7-8-9-10-14-24(31)18(22(30)25(26)23(24)35-25)15-20(34-17(3)28)19(33-16(2)27)12-11-13-21(29)32-4/h6-7,9-10,15,19-20,23,31H,5,8,11-14H2,1-4H3/b7-6+,10-9+,18-15+/t19-,20-,23+,24-,25-/m0/s1

> <INCHI_KEY>
ZXSDFJZDMJBPKR-ZISWEUEQSA-N

> <FORMULA>
C25H33ClO9

> <MOLECULAR_WEIGHT>
512.98

> <EXACT_MASS>
512.1813103

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.05330084980603

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (5S,6S)-5,6-bis(acetyloxy)-7-[(1S,3Z,4S,5R)-1-chloro-4-hydroxy-4-[(2E,5E)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate

> <JCHEM_LOGP>
3.7062688503333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.814749585435507

> <JCHEM_PKA_STRONGEST_BASIC>
-3.754628531330508

> <JCHEM_POLAR_SURFACE_AREA>
128.73

> <JCHEM_REFRACTIVITY>
128.94979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (5S,6S)-5,6-bis(acetyloxy)-7-[(1S,3Z,4S,5R)-1-chloro-4-hydroxy-4-[(2E,5E)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.385  12.473   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.840  12.977   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.004  11.969   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.459  12.473   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.623  11.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.332   9.952   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.496   8.944   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.205   7.432   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.369   6.424   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -9.250   7.687   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -7.245   5.372   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.733   5.663   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.725   4.498   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.229   3.043   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.221   1.879   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.708   2.170   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.725   0.424   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.212   4.789   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.204   3.625   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.692   3.916   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.316   2.752   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.828   3.043   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.333   4.498   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.837   1.879   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.349   2.170   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.708   6.245   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.716   7.409   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.229   7.118   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.212   8.864   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -7.899   3.977   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -7.154   2.629   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -9.427   4.168   0.000  0.00  0.00           C+0
HETATM   33 Cl   UNK     0      -9.776   2.668   0.000  0.00  0.00          Cl+0
HETATM   34  O   UNK     0     -10.882   4.672   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -9.718   5.680   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   35                                             
CONECT   10    9                                                            
CONECT   11    9   12   30                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   18   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   11   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   32    9                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₃ClO₉

Average Mass

512.9800 Da

Monoisotopic Mass

512.18131 Da

IUPAC Name

methyl (5S,6S)-5,6-bis(acetyloxy)-7-[(1S,3Z,4S,5R)-1-chloro-4-hydroxy-4-[(2E,5E)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate

Traditional Name

methyl (5S,6S)-5,6-bis(acetyloxy)-7-[(1S,3Z,4S,5R)-1-chloro-4-hydroxy-4-[(2E,5E)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H33ClO9/c1-5-6-7-8-9-10-14-24(31)18(22(30)25(26)23(24)35-25)15-20(34-17(3)28)19(33-16(2)27)12-11-13-21(29)32-4/h6-7,9-10,15,19-20,23,31H,5,8,11-14H2,1-4H3/b7-6+,10-9+,18-15+/t19-,20-,23+,24-,25-/m0/s1

InChI Key

ZXSDFJZDMJBPKR-ZISWEUEQSA-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

Species Name	Source	Reference
Carijoa riisei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as clavulones and derivatives. These are ester derivatives of prostanoids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Clavulones and derivatives

Alternative Parents

Substituents

Clavulone
Tricarboxylic acid or derivatives
Fatty acid methyl ester
Fatty acid ester
Oxane
Alpha-haloketone
Alpha-chloroketone
Methyl ester
Tertiary alcohol
Cyclic alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
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	3.71	ChemAxon
pKa (Strongest Acidic)	12.81	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	128.73 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	128.95 m³·mol⁻¹	ChemAxon
Polarizability	53.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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

101676769

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate (NP0243844)

MOL for NP0243844 (methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate)

3D MOL for NP0243844 (methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate)

3D SDF for NP0243844 (methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate)

3D-SDF for NP0243844 (methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate)

PDB for NP0243844 (methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate)

3D PDB for NP0243844 (methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate)

SMILES for NP0243844 (methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate)

INCHI for NP0243844 (methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate)

Structure for NP0243844 (methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate)

3D Structure for NP0243844 (methyl (5s,6s)-5,6-bis(acetyloxy)-7-[(1s,3z,4s,5r)-1-chloro-4-hydroxy-4-[(2e,5e)-octa-2,5-dien-1-yl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-ylidene]heptanoate)