NP-MRD: Showing NP-Card for (5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one (NP0183841)

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Record Information

Version

1.0

Created at

2022-09-03 22:49:42 UTC

Updated at

2022-09-03 22:49:42 UTC

NP-MRD ID

NP0183841

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one

Description

Bullatacin, also known as rolliniastatin-1 or asimicin, 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-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one is found in Annona squamosa. It was first documented in 2017 (PMID: 28254016). Based on a literature review a significant number of articles have been published on Bullatacin (PMID: 33563198) (PMID: 33235438) (PMID: 34112202) (PMID: 31452061).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200492D          

 44 46  0  0  1  0            999 V2000
    3.2919  -17.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204  -17.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

110112  0  0  0  0  0  0  0  0999 V2000
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 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
 33 35  1  0
 35 36  1  0
 36 37  2  0
 37 38  1  0
 38 39  1  0
 38 40  1  0
 40 41  1  0
 41 42  2  0
 44 13  1  0
 43 17  1  0
 41 36  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  1
 12 67  1  0
 13 68  1  6
 14 69  1  0
 14 70  1  0
 15 71  1  0
 15 72  1  0
 16 73  1  1
 17 74  1  6
 18 75  1  0
 18 76  1  0
 19 77  1  0
 19 78  1  0
 20 79  1  1
 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  1
 34103  1  0
 35104  1  0
 35105  1  0
 37106  1  0
 38107  1  6
 39108  1  0
 39109  1  0
 39110  1  0
M  END


  Mrv1652309042200492D          

 44 46  0  0  1  0            999 V2000
    3.2919  -17.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1204  -17.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7335  -16.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5620  -15.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751  -15.1462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0036  -14.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6166  -13.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4451  -12.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0582  -12.4282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8867  -11.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4998  -11.0692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2844  -11.3241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3283  -10.2622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5746   -9.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6608   -9.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4678   -8.9346    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8033   -8.1810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3908   -7.4665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9429   -6.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6966   -7.1890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4110   -6.7765    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4110   -5.9515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1255   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8400   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5544   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2689   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9834   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6979   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4123   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1268   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8413   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5557   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2702   -7.1890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2702   -8.0140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9847   -6.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6991   -7.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4528   -6.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0049   -7.4665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.8253   -7.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5924   -8.1810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7854   -8.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1723   -8.5615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6103   -8.0094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8803   -9.6491    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  6  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  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  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  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 36 41  1  0  0  0  0
 41 42  2  0  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>
NP0183841

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC[C@@H](O)[C@H]1CC[C@@H](O1)[C@H]1CC[C@@H](O1)[C@H](O)CCCCCCCCCC[C@@H](O)CC1=C[C@H](C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3/t28-,30+,31+,32+,33+,34+,35+,36+/m0/s1

> <INCHI_KEY>
MBABCNBNDNGODA-UOCXRWNNSA-N

> <FORMULA>
C37H66O7

> <MOLECULAR_WEIGHT>
622.928

> <EXACT_MASS>
622.480854465

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
78.70709762736666

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-3-[(2R,13R)-2,13-dihydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]tridecyl]-5-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
8.682191933333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.972764172872449

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.312197055299006

> <JCHEM_PKA_STRONGEST_BASIC>
-2.722022871174217

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
176.3966

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-3-[(2R,13R)-2,13-dihydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]tridecyl]-5-methyl-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       6.145 -33.346   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.825 -31.840   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.969 -30.810   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.649 -29.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.793 -28.273   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.473 -26.767   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.618 -25.736   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.298 -24.230   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.442 -23.199   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.122 -21.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.266 -20.662   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.731 -21.138   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.946 -19.156   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.539 -18.530   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.700 -16.998   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.207 -16.678   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.833 -15.271   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.063 -13.937   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.093 -12.793   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.500 -13.419   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.834 -12.649   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.834 -11.109   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      15.168 -13.419   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.501 -12.649   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.835 -13.419   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.169 -12.649   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.502 -13.419   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      21.836 -12.649   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      23.170 -13.419   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      24.503 -12.649   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.837 -13.419   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      27.171 -12.649   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      28.504 -13.419   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      28.504 -14.959   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      29.838 -12.649   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      31.172 -13.419   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      32.579 -12.793   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      33.609 -13.937   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      35.141 -13.776   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      32.839 -15.271   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      31.333 -14.951   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      30.188 -15.981   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      12.339 -14.951   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      10.977 -18.012   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   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   36   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

Value	Source
Rolliniastatin-1	MeSH
Asimicin	MeSH
Rolliniastatin-2	MeSH

Chemical Formula

C₃₇H₆₆O₇

Average Mass

622.9280 Da

Monoisotopic Mass

622.48085 Da

IUPAC Name

(5S)-3-[(2R,13R)-2,13-dihydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]tridecyl]-5-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5S)-3-[(2R,13R)-2,13-dihydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1R)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]tridecyl]-5-methyl-5H-furan-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)CCCCCCCCCC[C@@H](O)CC1=C[C@H](C)OC1=O

InChI Identifier

InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-22-24-35(43-33)36-25-23-34(44-36)32(40)21-18-15-12-9-8-10-13-16-19-30(38)27-29-26-28(2)42-37(29)41/h26,28,30-36,38-40H,3-25,27H2,1-2H3/t28-,30+,31+,32+,33+,34+,35+,36+/m0/s1

InChI Key

MBABCNBNDNGODA-UOCXRWNNSA-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 squamosa	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	8.68	ChemAxon
pKa (Strongest Acidic)	13.31	ChemAxon
pKa (Strongest Basic)	-2.7	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	176.4 m³·mol⁻¹	ChemAxon
Polarizability	78.71 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

C00001302

Chemspider ID

8136338

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bullatacin

METLIN ID

Not Available

PubChem Compound

9960731

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nordin N, Khimani K, Abd Ghani MF: Acetogenins Exhibit Potential BCL-XL Inhibitor for the Induction of Apoptosis in the Molecular Docking Study. Curr Drug Discov Technol. 2021;18(6):e010921191171. doi: 10.2174/1570163818666210204202426. [PubMed:33563198 ]
Shi JF, Wu P, Cheng XL, Wei XY, Jiang ZH: Synthesis and Cytotoxic Property of Annonaceous Acetogenin Glycoconjugates. Drug Des Devel Ther. 2020 Nov 17;14:4993-5004. doi: 10.2147/DDDT.S259547. eCollection 2020. [PubMed:33235438 ]
Fan F, Shen P, Ma Y, Ma W, Wu H, Liu H, An Q: Bullatacin triggers immunogenic cell death of colon cancer cells by activating endoplasmic reticulum chaperones. J Inflamm (Lond). 2021 Jun 10;18(1):23. doi: 10.1186/s12950-021-00289-1. [PubMed:34112202 ]
Pumiputavon K, Chaowasku T, Saenjum C, Osathanunkul M, Wungsintaweekul B, Chawansuntati K, Lithanatudom P, Wipasa J: Cytotoxic and cytostatic effects of four Annonaceae plants on human cancer cell lines. In Vitro Cell Dev Biol Anim. 2019 Oct;55(9):723-732. doi: 10.1007/s11626-019-00393-w. Epub 2019 Aug 26. [PubMed:31452061 ]
Bonneau N, Baloul L, Bajin Ba Ndob I, Senejoux F, Champy P: The fruit of Annona squamosa L. as a source of environmental neurotoxins: From quantification of squamocin to annotation of Annonaceous acetogenins by LC-MS/MS analysis. Food Chem. 2017 Jul 1;226:32-40. doi: 10.1016/j.foodchem.2017.01.042. Epub 2017 Jan 11. [PubMed:28254016 ]
LOTUS database [Link]

Showing NP-Card for (5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one (NP0183841)

MOL for NP0183841 ((5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one)

3D MOL for NP0183841 ((5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one)

3D SDF for NP0183841 ((5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one)

3D-SDF for NP0183841 ((5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one)

PDB for NP0183841 ((5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one)

3D PDB for NP0183841 ((5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one)

SMILES for NP0183841 ((5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one)

INCHI for NP0183841 ((5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one)

Structure for NP0183841 ((5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one)

3D Structure for NP0183841 ((5s)-3-[(2r,13r)-2,13-dihydroxy-13-[(2r,2'r,5r,5'r)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]tridecyl]-5-methyl-5h-furan-2-one)