NP-MRD: Showing NP-Card for (5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one (NP0281204)

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Record Information

Version

2.0

Created at

2022-09-09 07:24:33 UTC

Updated at

2022-09-09 07:24:33 UTC

NP-MRD ID

NP0281204

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one

Description

Reticulatacin belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. (5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one is found in Annona reticulata. (5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one was first documented in 2002 (PMID: 12434986). Based on a literature review a small amount of articles have been published on reticulatacin (PMID: 19673468) (PMID: 17928696) (PMID: 20733975).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092209242D          

 42 43  0  0  1  0            999 V2000
   -0.4065  -14.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0710  -14.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7495  -14.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0851  -13.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9055  -13.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411  -12.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0616  -12.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971  -11.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176  -11.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532  -10.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3737  -10.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7092   -9.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5297   -9.8908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0146  -10.5582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8653   -9.1371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4528   -8.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0048   -7.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7585   -8.1451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4729   -7.7326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4729   -6.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1874   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9019   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6163   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3308   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0453   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7598   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4742   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1887   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9032   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6176   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3321   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0466   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7611   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4755   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1900   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9437   -7.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4957   -8.4226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.3162   -8.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0832   -9.1371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2762   -8.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6631   -9.5176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6722   -8.9656    0.0000 O   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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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
 13 14  1  6  0  0  0
 15 13  1  1  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  6  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 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  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 35 40  1  0  0  0  0
 40 41  2  0  0  0  0
 18 42  1  0  0  0  0
 15 42  1  0  0  0  0
M  END


  Mrv1652309092209242D          

 42 43  0  0  1  0            999 V2000
   -0.4065  -14.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0710  -14.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7495  -14.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0851  -13.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9055  -13.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411  -12.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0616  -12.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3971  -11.6568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2176  -11.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5532  -10.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3737  -10.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7092   -9.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5297   -9.8908    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0146  -10.5582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8653   -9.1371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4528   -8.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0048   -7.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7585   -8.1451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4729   -7.7326    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4729   -6.9076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1874   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9019   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6163   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3308   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0453   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7598   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4742   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1887   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9032   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6176   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3321   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0466   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7611   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4755   -7.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1900   -8.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9437   -7.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4957   -8.4226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.3162   -8.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0832   -9.1371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2762   -8.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6631   -9.5176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6722   -8.9656    0.0000 O   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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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
 13 14  1  6  0  0  0
 15 13  1  1  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  6  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 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  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 35 40  1  0  0  0  0
 40 41  2  0  0  0  0
 18 42  1  0  0  0  0
 15 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281204

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC[C@@H](O)[C@H]1CC[C@@H](O1)[C@H](O)CCCCCCCCCCCCCCC1=C[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H68O5/c1-3-4-5-6-7-8-14-17-20-23-26-33(38)35-28-29-36(42-35)34(39)27-24-21-18-15-12-10-9-11-13-16-19-22-25-32-30-31(2)41-37(32)40/h30-31,33-36,38-39H,3-29H2,1-2H3/t31-,33+,34+,35+,36+/m0/s1

> <INCHI_KEY>
BDGWQMLWIGDEKO-AYJUPLJXSA-N

> <FORMULA>
C37H68O5

> <MOLECULAR_WEIGHT>
592.946

> <EXACT_MASS>
592.50667529

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
78.50150854308536

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-3-[(15R)-15-hydroxy-15-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
11.368829022000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.998073257924691

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.333150931855364

> <JCHEM_PKA_STRONGEST_BASIC>
-3.148664983209411

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
175.2062

> <JCHEM_ROTATABLE_BOND_COUNT>
28

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-3-[(15R)-15-hydroxy-15-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.759 -27.870   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.132 -26.463   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.399 -26.302   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.025 -24.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.557 -24.734   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.183 -23.327   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.715 -23.166   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.341 -21.759   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.873 -21.598   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.499 -20.192   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.031 -20.031   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.657 -18.624   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.189 -18.463   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      13.094 -19.709   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.815 -17.056   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.045 -15.722   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.076 -14.578   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.482 -15.204   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.816 -14.434   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      15.816 -12.894   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      17.150 -15.204   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      18.484 -14.434   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.817 -15.204   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      21.151 -14.434   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      22.485 -15.204   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.818 -14.434   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      25.152 -15.204   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.486 -14.434   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      27.819 -15.204   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      29.153 -14.434   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      30.487 -15.204   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      31.820 -14.434   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      33.154 -15.204   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      34.488 -14.434   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      35.821 -15.204   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      37.228 -14.578   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      38.259 -15.722   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      39.790 -15.561   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      37.489 -17.056   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      35.982 -16.736   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      34.838 -17.766   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      14.321 -16.736   0.000  0.00  0.00           O+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                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   42                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   42                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   35   41                                                  
CONECT   41   40                                                            
CONECT   42   18   15                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₆₈O₅

Average Mass

592.9460 Da

Monoisotopic Mass

592.50668 Da

IUPAC Name

(5S)-3-[(15R)-15-hydroxy-15-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5S)-3-[(15R)-15-hydroxy-15-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCC[C@@H](O)[C@H]1CC[C@@H](O1)[C@H](O)CCCCCCCCCCCCCCC1=C[C@H](C)OC1=O

InChI Identifier

InChI=1S/C37H68O5/c1-3-4-5-6-7-8-14-17-20-23-26-33(38)35-28-29-36(42-35)34(39)27-24-21-18-15-12-10-9-11-13-16-19-22-25-32-30-31(2)41-37(32)40/h30-31,33-36,38-39H,3-29H2,1-2H3/t31-,33+,34+,35+,36+/m0/s1

InChI Key

BDGWQMLWIGDEKO-AYJUPLJXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annona reticulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Dihydrofuran
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	11.37	ChemAxon
pKa (Strongest Acidic)	13.33	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	175.21 m³·mol⁻¹	ChemAxon
Polarizability	78.5 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

C00049858

Chemspider ID

9279065

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11103924

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abdel Ghani SB, Chapman JM, Figadere B, Herniman JM, Langley GJ, Niemann S, Brown RC: Total synthesis and stereochemical assignment of cis-uvariamicin I and cis-reticulatacin. J Org Chem. 2009 Sep 18;74(18):6924-8. doi: 10.1021/jo9012578. [PubMed:19673468 ]
Fall D, Gleye C, Franck X, Laurens A, Hocquemiller R: Cis-bullatencin, a linear acetogenin from roots of Uvaria chamae. Nat Prod Lett. 2002 Oct;16(5):315-21. doi: 10.1080/10575630290026437. [PubMed:12434986 ]
Makabe H: Synthesis of annonaceous acetogenins from muricatacin. Biosci Biotechnol Biochem. 2007 Oct;71(10):2367-74. doi: 10.1271/bbb.70202. Epub 2007 Oct 7. [PubMed:17928696 ]
Abdel Ghani SB, Brown LJ, Figadere B, Brown RC: Total synthesis of cis-reticulatacin-10-ones A and B: absolute stereochemical assignment. Org Biomol Chem. 2010 Oct 21;8(20):4543-5. doi: 10.1039/c0ob00259c. Epub 2010 Aug 23. [PubMed:20733975 ]
LOTUS database [Link]

Showing NP-Card for (5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one (NP0281204)

MOL for NP0281204 ((5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one)

3D MOL for NP0281204 ((5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one)

3D SDF for NP0281204 ((5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one)

3D-SDF for NP0281204 ((5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one)

PDB for NP0281204 ((5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one)

3D PDB for NP0281204 ((5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one)

SMILES for NP0281204 ((5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one)

INCHI for NP0281204 ((5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one)

Structure for NP0281204 ((5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one)

3D Structure for NP0281204 ((5s)-3-[(15r)-15-hydroxy-15-[(2r,5r)-5-[(1r)-1-hydroxytridecyl]oxolan-2-yl]pentadecyl]-5-methyl-5h-furan-2-one)