NP-MRD: Showing NP-Card for (5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one (NP0228330)

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Record Information

Version

1.0

Created at

2022-09-06 07:56:50 UTC

Updated at

2022-09-06 07:56:50 UTC

NP-MRD ID

NP0228330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one

Description

Bullatacinone, also known as asimicinone, 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)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one is found in Asimina triloba. It was first documented in 1994 (PMID: 8075893). Based on a literature review a significant number of articles have been published on Bullatacinone (PMID: 8676130) (PMID: 11962508) (PMID: 9564733) (PMID: 7586047).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062209562D          

 44 46  0  0  1  0            999 V2000
    2.2300  -16.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0585  -16.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 37 39  2  0
 35 40  1  0
 40 41  2  0
 40 42  1  0
 44 13  1  0
 43 17  1  0
 42 33  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  1
 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
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 19 78  1  0
 20 79  1  6
 21 80  1  1
 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  6
 34103  1  0
 34104  1  0
 35105  1  6
 36106  1  0
 36107  1  0
 38108  1  0
 38109  1  0
 38110  1  0
M  END


  Mrv1652309062209562D          

 44 46  0  0  1  0            999 V2000
    2.2300  -16.9080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0585  -16.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6716  -15.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5001  -14.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1132  -14.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9416  -13.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5547  -12.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3832  -12.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9963  -11.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8248  -10.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4379  -10.1130    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2225  -10.3680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -9.3061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5127   -8.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5989   -8.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4059   -7.9785    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7414   -7.2248    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3289   -6.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8810   -5.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6346   -6.2328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3491   -5.8203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3491   -4.9953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0636   -6.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7781   -5.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4925   -6.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2070   -5.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9215   -6.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6359   -5.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3504   -6.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0649   -5.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7794   -6.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4938   -5.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2083   -6.2328    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.9620   -5.8972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5140   -6.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3345   -6.4241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8194   -7.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6399   -7.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4838   -7.8452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1015   -7.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4371   -7.9785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2945   -7.0533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484   -7.0533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8184   -8.6930    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  6  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  1  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
 33 32  1  1  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  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 35 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 33 42  1  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>
NP0228330

> <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]1CC(CC(C)=O)C(=O)O1

> <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)21-18-15-12-9-8-10-13-16-19-30-27-29(26-28(2)38)37(41)42-30/h29-36,39-40H,3-27H2,1-2H3/t29?,30-,31+,32-,33-,34-,35+,36+/m0/s1

> <INCHI_KEY>
KGGVWMAPBXIMEM-YPSBWLOUSA-N

> <FORMULA>
C37H66O7

> <MOLECULAR_WEIGHT>
622.928

> <EXACT_MASS>
622.480854465

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
78.03464915096598

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-5-[(11S)-11-hydroxy-11-[(2R,2'R,5S,5'S)-5'-[(1R)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one

> <JCHEM_LOGP>
8.472050788999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.500804158429037

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.898978347148773

> <JCHEM_PKA_STRONGEST_BASIC>
-3.148665094183956

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
174.5437

> <JCHEM_ROTATABLE_BOND_COUNT>
25

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-5-[(11S)-11-hydroxy-11-[(2R,2'R,5S,5'S)-5'-[(1R)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-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       4.163 -31.562   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.843 -30.055   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.987 -29.025   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.667 -27.519   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.811 -26.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.491 -24.982   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.636 -23.951   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.315 -22.445   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.460 -21.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.140 -19.908   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.284 -18.878   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.749 -19.354   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.964 -17.371   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.557 -16.745   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.718 -15.213   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.224 -14.893   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.851 -13.486   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.081 -12.153   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.111 -11.008   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.518 -11.635   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.852 -10.865   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.852  -9.325   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.185 -11.635   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.519 -10.865   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.853 -11.635   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.186 -10.865   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.520 -11.635   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.854 -10.865   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      21.187 -11.635   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      22.521 -10.865   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      23.855 -11.635   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      25.188 -10.865   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      26.522 -11.635   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      27.929 -11.008   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      28.959 -12.153   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      30.491 -11.992   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      31.396 -13.238   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      32.928 -13.077   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      30.770 -14.644   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      28.189 -13.486   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      28.816 -14.893   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      26.683 -13.166   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      10.357 -13.166   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       8.994 -16.227   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   42                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   35   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   33                                                       
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
2,4-trans-Asimicinone	MeSH
Asimicinone	MeSH
2,4-cis-Asimicinone	MeSH

Chemical Formula

C₃₇H₆₆O₇

Average Mass

622.9280 Da

Monoisotopic Mass

622.48085 Da

IUPAC Name

(5S)-5-[(11S)-11-hydroxy-11-[(2R,2'R,5S,5'S)-5'-[(1R)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one

Traditional Name

(5S)-5-[(11S)-11-hydroxy-11-[(2R,2'R,5S,5'S)-5'-[(1R)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-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]1CC(CC(C)=O)C(=O)O1

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)21-18-15-12-9-8-10-13-16-19-30-27-29(26-28(2)38)37(41)42-30/h29-36,39-40H,3-27H2,1-2H3/t29?,30-,31+,32-,33-,34-,35+,36+/m0/s1

InChI Key

KGGVWMAPBXIMEM-YPSBWLOUSA-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
Asimina triloba	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
Ketone
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Alcohol
Organooxygen compound
Carbonyl group
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	8.47	ChemAxon
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	174.54 m³·mol⁻¹	ChemAxon
Polarizability	78.03 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

4572942

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5459112

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Woo MH, Cho KY, Zhang Y, Zeng L, Gu ZM, McLaughlin JL: Asimilobin and cis- and trans-murisolinones, novel bioactive Annonaceous acetogenins from the seeds of Asimina triloba. J Nat Prod. 1995 Oct;58(10):1533-42. doi: 10.1021/np50124a009. [PubMed:8676130 ]
Rodier S, Le Huerou Y, Renoux B, Doyon J, Renard P, Pierre A, Gesson JP, Gree R: New cytotoxic analogues of annonaceous acetogenins. Anticancer Drug Des. 2001 Apr-Jun;16(2-3):109-17. [PubMed:11962508 ]
Chang FR, Chen JL, Chiu HF, Wu MJ, Wu YC: Acetogenins from seeds of Annona reticulata. Phytochemistry. 1998 Mar;47(6):1057-61. doi: 10.1016/s0031-9422(97)00675-4. [PubMed:9564733 ]
Landolt JL, Ahammadsahib KI, Hollingworth RM, Barr R, Crane FL, Buerck NL, McCabe GP, McLaughlin JL: Determination of structure-activity relationships of Annonaceous acetogenins by inhibition of oxygen uptake in rat liver mitochondria. Chem Biol Interact. 1995 Oct 20;98(1):1-13. doi: 10.1016/0009-2797(95)03628-y. [PubMed:7586047 ]
Gu ZM, Fang XP, Hui YH, McLaughlin JL: 10-, 12-, and 29-hydroxybullatacinones: new cytotoxic Annonaceous acetogenins from Annona bullata Rich (Annonaceae). Nat Toxins. 1994;2(2):49-55. doi: 10.1002/nt.2620020202. [PubMed:8075893 ]
LOTUS database [Link]

Showing NP-Card for (5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one (NP0228330)

MOL for NP0228330 ((5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one)

3D MOL for NP0228330 ((5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one)

3D SDF for NP0228330 ((5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one)

3D-SDF for NP0228330 ((5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one)

PDB for NP0228330 ((5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one)

3D PDB for NP0228330 ((5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one)

SMILES for NP0228330 ((5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one)

INCHI for NP0228330 ((5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one)

Structure for NP0228330 ((5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one)

3D Structure for NP0228330 ((5s)-5-[(11s)-11-hydroxy-11-[(2r,2'r,5s,5's)-5'-[(1r)-1-hydroxyundecyl]-[2,2'-bioxolan]-5-yl]undecyl]-3-(2-oxopropyl)oxolan-2-one)