NP-MRD: Showing NP-Card for (4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one (NP0228580)

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Record Information

Version

1.0

Created at

2022-09-06 08:17:37 UTC

Updated at

2022-09-06 08:17:37 UTC

NP-MRD ID

NP0228580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one

Description

LAHERRADURIN 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. (4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one is found in Annona cherimola and Annona glabra. It was first documented in 2004 (PMID: 15503356). Based on a literature review a significant number of articles have been published on LAHERRADURIN (PMID: 30607643) (PMID: 23180140) (PMID: 19170140) (PMID: 18264981).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062210172D          

 44 46  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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 15 16  1  0
 16 44  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 43  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 41  1  0
 41 42  1  0
 41 39  1  0
 39 40  1  0
 39 38  1  0
 38 36  1  0
 36 37  2  0
 44 13  1  0
 43 17  1  0
 36 35  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  2 48  1  0
  2 49  1  0
  3 50  1  0
  3 51  1  0
  4 52  1  0
  4 53  1  0
  5 54  1  0
  5 55  1  0
  6 56  1  0
  6 57  1  0
  7 58  1  0
  7 59  1  0
  8 60  1  0
  8 61  1  0
  9 62  1  0
  9 63  1  0
 10 64  1  0
 10 65  1  0
 11 66  1  6
 12 67  1  0
 13 68  1  1
 14 69  1  0
 14 70  1  0
 15 71  1  0
 15 72  1  0
 16 73  1  6
 17 74  1  1
 18 75  1  0
 18 76  1  0
 19 77  1  0
 19 78  1  0
 20 79  1  6
 21 80  1  6
 22 81  1  0
 23 82  1  0
 23 83  1  0
 24 84  1  0
 24 85  1  0
 25 86  1  0
 25 87  1  0
 26 88  1  0
 26 89  1  0
 27 90  1  0
 27 91  1  0
 28 92  1  0
 28 93  1  0
 29 94  1  0
 29 95  1  0
 30 96  1  0
 30 97  1  0
 31 98  1  0
 31 99  1  0
 32100  1  0
 32101  1  0
 33102  1  0
 33103  1  0
 34104  1  0
 34105  1  0
 35106  1  1
 41111  1  1
 42112  1  0
 39107  1  1
 40108  1  0
 40109  1  0
 40110  1  0
M  END


  Mrv1652309062210172D          

 44 46  0  0  1  0            999 V2000
  -12.4048  -11.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7917  -10.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0071  -11.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3940  -10.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6094  -10.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9963  -10.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2117  -10.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5986   -9.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8139  -10.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2008   -9.6621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4162   -9.9170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2447  -10.7240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8031   -9.3650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8894   -8.5445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1357   -8.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5837   -8.8221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7632   -8.7358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3507   -8.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5437   -8.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575   -9.0134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7430   -9.4259    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7430  -10.2509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0285   -9.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6859   -9.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -9.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1149   -9.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8294   -9.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5438   -9.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2583   -9.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9728   -9.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6872   -9.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4017   -9.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1162   -9.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8306   -9.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5451   -9.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6314   -8.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0183   -7.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4383   -8.0213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8508   -8.7358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6713   -8.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2988   -9.3489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4703  -10.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2111   -9.3489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9962   -9.5365    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  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  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  1  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  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  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 35 41  1  0  0  0  0
 41 42  1  6  0  0  0
 20 43  1  0  0  0  0
 17 43  1  1  0  0  0
 16 44  1  0  0  0  0
 13 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC[C@H](O)[C@H]1CC[C@@H](O1)[C@H]1CC[C@@H](O1)[C@H](O)CCCCCCCCCCCCC1[C@@H](O)[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H68O7/c1-3-4-5-6-7-13-16-19-22-30(38)32-24-26-34(43-32)35-27-25-33(44-35)31(39)23-20-17-14-11-9-8-10-12-15-18-21-29-36(40)28(2)42-37(29)41/h28-36,38-40H,3-27H2,1-2H3/t28-,29?,30-,31+,32+,33+,34+,35+,36-/m0/s1

> <INCHI_KEY>
FTTBSOBXDJECAA-SLOXALGKSA-N

> <FORMULA>
C37H68O7

> <MOLECULAR_WEIGHT>
624.944

> <EXACT_MASS>
624.49650453

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
79.5257418094101

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,5S)-4-hydroxy-3-[(13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1S)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]tridecyl]-5-methyloxolan-2-one

> <JCHEM_LOGP>
8.910285819333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.043763373216251

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.476294113425656

> <JCHEM_PKA_STRONGEST_BASIC>
-3.148665094183956

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
175.2127

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4R,5S)-4-hydroxy-3-[(13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1S)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]tridecyl]-5-methyloxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0     -23.156 -21.285   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -22.011 -20.254   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -20.547 -20.730   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -19.402 -19.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -17.938 -20.176   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -16.793 -19.145   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -15.328 -19.621   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -14.184 -18.590   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.719 -19.066   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -11.575 -18.036   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -10.110 -18.512   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -9.790 -20.018   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -8.966 -17.481   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.127 -15.950   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.720 -15.323   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.690 -16.468   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.158 -16.307   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.388 -14.973   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.882 -15.293   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.721 -16.825   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.387 -17.595   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.387 -19.135   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.053 -16.825   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.280 -17.595   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.614 -16.825   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.948 -17.595   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.281 -16.825   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.615 -17.595   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.949 -16.825   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.282 -17.595   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.616 -16.825   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.950 -17.595   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.284 -16.825   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.617 -17.595   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.951 -16.825   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.112 -15.293   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.967 -14.263   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      17.618 -14.973   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      18.388 -16.307   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      19.920 -16.468   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      17.358 -17.451   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      17.678 -18.958   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -4.127 -17.451   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -7.460 -17.802   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   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   44                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   44                                                  
CONECT   17   16   18   43                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   43                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   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   41                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   35   42                                                  
CONECT   42   41                                                            
CONECT   43   20   17                                                       
CONECT   44   16   13                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₆₈O₇

Average Mass

624.9440 Da

Monoisotopic Mass

624.49650 Da

IUPAC Name

(4R,5S)-4-hydroxy-3-[(13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1S)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]tridecyl]-5-methyloxolan-2-one

Traditional Name

(4R,5S)-4-hydroxy-3-[(13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1S)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]tridecyl]-5-methyloxolan-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC[C@H](O)[C@H]1CC[C@@H](O1)[C@H]1CC[C@@H](O1)[C@H](O)CCCCCCCCCCCCC1[C@@H](O)[C@H](C)OC1=O

InChI Identifier

InChI=1S/C37H68O7/c1-3-4-5-6-7-13-16-19-22-30(38)32-24-26-34(43-32)35-27-25-33(44-35)31(39)23-20-17-14-11-9-8-10-12-15-18-21-29-36(40)28(2)42-37(29)41/h28-36,38-40H,3-27H2,1-2H3/t28-,29?,30-,31+,32+,33+,34+,35+,36-/m0/s1

InChI Key

FTTBSOBXDJECAA-SLOXALGKSA-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
Annona cherimola	LOTUS Database	35616633
Annona glabra	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
Gamma butyrolactone
Oxolane
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
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	8.91	ChemAxon
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	175.21 m³·mol⁻¹	ChemAxon
Polarizability	79.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00044211

Chemspider ID

23231116

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44374350

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Duran-Ruiz CA, Cruz-Ortega R, Zaldivar-Riveron A, Zavaleta-Mancera HA, De-la-Cruz-Chacon I, Gonzalez-Esquinca AR: Ontogenic synchronization of Bephratelloides cubensis, Annona macroprophyllata seeds and acetogenins from Annonaceae. J Plant Res. 2019 Jan;132(1):81-91. doi: 10.1007/s10265-018-01078-3. Epub 2019 Jan 3. [PubMed:30607643 ]
de Pedro N, Cautain B, Melguizo A, Vicente F, Genilloud O, Pelaez F, Tormo JR: Mitochondrial complex I inhibitors, acetogenins, induce HepG2 cell death through the induction of the complete apoptotic mitochondrial pathway. J Bioenerg Biomembr. 2013 Feb;45(1-2):153-64. doi: 10.1007/s10863-012-9489-1. Epub 2012 Nov 21. [PubMed:23180140 ]
Schlie-Guzman MA, Garcia-Carranca A, Gonzalez-Esquinca AR: In vitro and in vivo antiproliferative activity of laherradurin and cherimolin-2 of Annona diversifolia Saff. Phytother Res. 2009 Aug;23(8):1128-33. doi: 10.1002/ptr.2760. [PubMed:19170140 ]
Rodriguez-Enriquez S, Gallardo-Perez JC, Aviles-Salas A, Marin-Hernandez A, Carreno-Fuentes L, Maldonado-Lagunas V, Moreno-Sanchez R: Energy metabolism transition in multi-cellular human tumor spheroids. J Cell Physiol. 2008 Jul;216(1):189-97. doi: 10.1002/jcp.21392. [PubMed:18264981 ]
Barrachina I, Neske A, Granell S, Bermejo A, Chahboune N, El Aouad N, Alvarez O, Bardon A, Zafra-Polo MC: Tucumanin, a beta-hydroxy-gamma-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I. Planta Med. 2004 Sep;70(9):866-8. doi: 10.1055/s-2004-827237. [PubMed:15503356 ]
LOTUS database [Link]

Showing NP-Card for (4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one (NP0228580)

MOL for NP0228580 ((4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one)

3D MOL for NP0228580 ((4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one)

3D SDF for NP0228580 ((4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one)

3D-SDF for NP0228580 ((4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one)

PDB for NP0228580 ((4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one)

3D PDB for NP0228580 ((4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one)

SMILES for NP0228580 ((4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one)

INCHI for NP0228580 ((4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one)

Structure for NP0228580 ((4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one)

3D Structure for NP0228580 ((4r,5s)-4-hydroxy-3-[(13r)-13-hydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1s)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyloxolan-2-one)