NP-MRD: Showing NP-Card for Simonin IV (NP0045501)

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Record Information

Version

1.0

Created at

2022-03-17 19:21:02 UTC

Updated at

2022-03-17 19:21:03 UTC

NP-MRD ID

NP0045501

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Simonin IV

Description

Epomusenin A 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. Epomusenin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Epomusenin A has been detected, but not quantified in, alcoholic beverages and fruits. It was first documented in 2000 (PMID: 11413487). This could make epomusenin a a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061304572D          

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M  END


  Mrv0541 05061304572D          

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   22.1486    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2920    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2920    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2920    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8644    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8644   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4354   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7210    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5762    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4341    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8631    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2907    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1486    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5775   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7197    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 19  1  0  0  0  0
 22 18  1  0  0  0  0
 23 21  1  0  0  0  0
 24 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26 23  1  0  0  0  0
 27 22  1  0  0  0  0
 28 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30 14  1  0  0  0  0
 31 26  1  0  0  0  0
 32 28  1  0  0  0  0
 33 29  1  0  0  0  0
 34 27  1  0  0  0  0
 35 30  1  0  0  0  0
 36 31  1  0  0  0  0
 37 32  1  0  0  0  0
 38 33  1  0  0  0  0
 39 34  1  0  0  0  0
 40  4  1  0  0  0  0
 41  5  1  0  0  0  0
 42  6  1  0  0  0  0
 43  7  1  0  0  0  0
 44  8  1  0  0  0  0
 45 35  1  0  0  0  0
 45 36  1  0  0  0  0
 46 37  1  0  0  0  0
 47 38  1  0  0  0  0
 48 39  1  0  0  0  0
 49 40  1  0  0  0  0
 50 41  1  0  0  0  0
 51 49  1  0  0  0  0
 52 50  1  0  0  0  0
 54 51  1  0  0  0  0
 55 53  1  0  0  0  0
 57 42  1  0  0  0  0
 57 53  1  0  0  0  0
 58 43  1  0  0  0  0
 58 56  1  0  0  0  0
 59 44  1  0  0  0  0
 60 52  1  0  0  0  0
 61 56  1  0  0  0  0
 62 59  1  0  0  0  0
 63 62  1  0  0  0  0
 64 54  1  0  0  0  0
 65 55  1  0  0  0  0
 66 60  1  0  0  0  0
 67 61  1  0  0  0  0
 68 63  1  0  0  0  0
 69 46  2  0  0  0  0
 70 47  2  0  0  0  0
 71 48  2  0  0  0  0
 72 49  1  0  0  0  0
 73 50  1  0  0  0  0
 74 51  1  0  0  0  0
 75 52  1  0  0  0  0
 76 53  1  0  0  0  0
 77 54  1  0  0  0  0
 78 55  1  0  0  0  0
 79 56  1  0  0  0  0
 80 40  1  0  0  0  0
 80 64  1  0  0  0  0
 81 41  1  0  0  0  0
 81 66  1  0  0  0  0
 82 42  1  0  0  0  0
 82 65  1  0  0  0  0
 83 43  1  0  0  0  0
 83 67  1  0  0  0  0
 84 44  1  0  0  0  0
 84 68  1  0  0  0  0
 85 45  1  0  0  0  0
 85 66  1  0  0  0  0
 86 46  1  0  0  0  0
 86 57  1  0  0  0  0
 87 47  1  0  0  0  0
 87 61  1  0  0  0  0
 88 48  1  0  0  0  0
 88 63  1  0  0  0  0
 89 58  1  0  0  0  0
 89 68  1  0  0  0  0
 90 59  1  0  0  0  0
 90 65  1  0  0  0  0
 91 60  1  0  0  0  0
 91 67  1  0  0  0  0
 92 62  1  0  0  0  0
 92 64  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045501

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCC(=O)OC1C(C)OC(OC2C(C)OC(OC3C(C)OC4OC5C(O)C(O)C(C)OC5OC(CCCCC)CCCCCCCCCC(=O)OC4C3O)C(OC(=O)CCCCCCCCC)C2OC2OC(C)C(O)C(O)C2O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C68H120O24/c1-9-12-15-17-19-20-24-28-32-37-46(69)86-57-42(6)82-65(55(78)53(57)76)90-59-44(8)84-68(63(88-48(71)39-34-27-22-18-16-13-10-2)62(59)92-64-54(77)51(74)49(72)40(4)80-64)89-58-43(7)83-67-61(56(58)79)87-47(70)38-33-29-25-21-23-26-31-36-45(35-30-14-11-3)85-66-60(91-67)52(75)50(73)41(5)81-66/h40-45,49-68,72-79H,9-39H2,1-8H3

> <INCHI_KEY>
PIPJWVLVHFNOQG-UHFFFAOYSA-N

> <FORMULA>
C68H120O24

> <MOLECULAR_WEIGHT>
1321.666

> <EXACT_MASS>
1320.816954768

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
148.57637816308448

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{[5-(decanoyloxy)-2-methyl-6-({7,25,26-trihydroxy-5,24-dimethyl-10-oxo-20-pentyl-2,4,9,21,23-pentaoxatricyclo[20.4.0.0³,⁸]hexacosan-6-yl}oxy)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl dodecanoate

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
11.311128134999997

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.30246679625018

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.846847575410182

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6121826090014517

> <JCHEM_POLAR_SURFACE_AREA>
333.0400000000001

> <JCHEM_REFRACTIVITY>
330.78169999999983

> <JCHEM_ROTATABLE_BOND_COUNT>
32

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[5-(decanoyloxy)-2-methyl-6-({7,25,26-trihydroxy-5,24-dimethyl-10-oxo-20-pentyl-2,4,9,21,23-pentaoxatricyclo[20.4.0.0³,⁸]hexacosan-6-yl}oxy)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl dodecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      22.673  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      50.680  13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.342  14.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      49.346   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.342   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      38.677  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.344   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      41.344  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.006  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      52.014  13.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      34.676  13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.340  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      52.014  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.676  12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.674  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      50.680  10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.007  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      50.680   9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.341  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.675  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      41.344  13.090   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      49.346   8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      40.010  13.860   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      32.008  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      42.678  13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      38.677  13.090   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      49.346   6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      33.342  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      44.011  13.090   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      36.009  11.550   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      38.677  11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      34.676  -4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      44.011  11.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      48.013   6.160   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      36.009  10.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      37.343  10.780   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      36.009  -5.390   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      42.678  10.780   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      48.013   4.620   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      49.346   2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      34.676   4.620   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      40.010  -3.080   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      41.344   3.850   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      42.678   0.000   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      37.343   9.240   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      37.343  -4.620   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      42.678   9.240   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      46.679   3.850   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      50.680   1.540   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      36.009   3.850   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      50.680   0.000   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      37.343   4.620   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      41.344  -5.390   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      49.346  -0.770   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      42.678  -4.620   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      42.678   6.160   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      40.010  -4.620   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      42.678   4.620   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      44.011  -0.770   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      37.343   6.160   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      41.344   6.930   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      45.345   0.000   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      45.345   1.540   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      48.013   0.000   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      42.678  -3.080   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      36.009   6.930   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      40.010   6.160   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      44.011   2.310   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      37.343  -3.080   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0      44.011   8.470   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0      45.345   4.620   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0      52.014   2.310   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      36.009   2.310   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      52.014  -0.770   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0      38.677   3.850   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0      41.344  -6.930   0.000  0.00  0.00           O+0
HETATM   77  O   UNK     0      49.346  -2.310   0.000  0.00  0.00           O+0
HETATM   78  O   UNK     0      44.011  -5.390   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0      44.011   6.930   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0      48.013   1.540   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0      34.676   6.160   0.000  0.00  0.00           O+0
HETATM   82  O   UNK     0      41.344  -2.310   0.000  0.00  0.00           O+0
HETATM   83  O   UNK     0      40.010   4.620   0.000  0.00  0.00           O+0
HETATM   84  O   UNK     0      42.678   1.540   0.000  0.00  0.00           O+0
HETATM   85  O   UNK     0      36.009   8.470   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0      38.677  -5.390   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0      41.344   8.470   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0      46.679   2.310   0.000  0.00  0.00           O+0
HETATM   89  O   UNK     0      44.011   3.850   0.000  0.00  0.00           O+0
HETATM   90  O   UNK     0      44.011  -2.310   0.000  0.00  0.00           O+0
HETATM   91  O   UNK     0      38.677   6.930   0.000  0.00  0.00           O+0
HETATM   92  O   UNK     0      46.679  -0.770   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   40                                                            
CONECT    5   41                                                            
CONECT    6   42                                                            
CONECT    7   43                                                            
CONECT    8   44                                                            
CONECT    9    1   12                                                       
CONECT   10    2   13                                                       
CONECT   11    3   14                                                       
CONECT   12    9   15                                                       
CONECT   13   10   16                                                       
CONECT   14   11   30                                                       
CONECT   15   12   17                                                       
CONECT   16   13   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   22                                                       
CONECT   19   17   20                                                       
CONECT   20   19   24                                                       
CONECT   21   23   25                                                       
CONECT   22   18   27                                                       
CONECT   23   21   26                                                       
CONECT   24   20   28                                                       
CONECT   25   21   29                                                       
CONECT   26   23   31                                                       
CONECT   27   22   34                                                       
CONECT   28   24   32                                                       
CONECT   29   25   33                                                       
CONECT   30   14   35                                                       
CONECT   31   26   36                                                       
CONECT   32   28   37                                                       
CONECT   33   29   38                                                       
CONECT   34   27   39                                                       
CONECT   35   30   45                                                       
CONECT   36   31   45                                                       
CONECT   37   32   46                                                       
CONECT   38   33   47                                                       
CONECT   39   34   48                                                       
CONECT   40    4   49   80                                                  
CONECT   41    5   50   81                                                  
CONECT   42    6   57   82                                                  
CONECT   43    7   58   83                                                  
CONECT   44    8   59   84                                                  
CONECT   45   35   36   85                                                  
CONECT   46   37   69   86                                                  
CONECT   47   38   70   87                                                  
CONECT   48   39   71   88                                                  
CONECT   49   40   51   72                                                  
CONECT   50   41   52   73                                                  
CONECT   51   49   54   74                                                  
CONECT   52   50   60   75                                                  
CONECT   53   55   57   76                                                  
CONECT   54   51   64   77                                                  
CONECT   55   53   65   78                                                  
CONECT   56   58   61   79                                                  
CONECT   57   42   53   86                                                  
CONECT   58   43   56   89                                                  
CONECT   59   44   62   90                                                  
CONECT   60   52   66   91                                                  
CONECT   61   56   67   87                                                  
CONECT   62   59   63   92                                                  
CONECT   63   62   68   88                                                  
CONECT   64   54   80   92                                                  
CONECT   65   55   82   90                                                  
CONECT   66   60   81   85                                                  
CONECT   67   61   83   91                                                  
CONECT   68   63   84   89                                                  
CONECT   69   46                                                            
CONECT   70   47                                                            
CONECT   71   48                                                            
CONECT   72   49                                                            
CONECT   73   50                                                            
CONECT   74   51                                                            
CONECT   75   52                                                            
CONECT   76   53                                                            
CONECT   77   54                                                            
CONECT   78   55                                                            
CONECT   79   56                                                            
CONECT   80   40   64                                                       
CONECT   81   41   66                                                       
CONECT   82   42   65                                                       
CONECT   83   43   67                                                       
CONECT   84   44   68                                                       
CONECT   85   45   66                                                       
CONECT   86   46   57                                                       
CONECT   87   47   61                                                       
CONECT   88   48   63                                                       
CONECT   89   58   68                                                       
CONECT   90   59   65                                                       
CONECT   91   60   67                                                       
CONECT   92   62   64                                                       
MASTER        0    0    0    0    0    0    0    0   92    0  194    0
END

View in JSmol

Synonyms

Value	Source
6-{[5-(decanoyloxy)-2-methyl-6-({7,25,26-trihydroxy-5,24-dimethyl-10-oxo-20-pentyl-2,4,9,21,23-pentaoxatricyclo[20.4.0.0³,⁸]hexacosan-6-yl}oxy)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl dodecanoic acid	Generator

Chemical Formula

C₆₈H₁₂₀O₂₄

Average Mass

1321.6660 Da

Monoisotopic Mass

1320.81695 Da

IUPAC Name

6-{[5-(decanoyloxy)-2-methyl-6-({7,25,26-trihydroxy-5,24-dimethyl-10-oxo-20-pentyl-2,4,9,21,23-pentaoxatricyclo[20.4.0.0³,⁸]hexacosan-6-yl}oxy)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl dodecanoate

Traditional Name

CAS Registry Number

151310-53-1

SMILES

CCCCCCCCCCCC(=O)OC1C(C)OC(OC2C(C)OC(OC3C(C)OC4OC5C(O)C(O)C(C)OC5OC(CCCCC)CCCCCCCCCC(=O)OC4C3O)C(OC(=O)CCCCCCCCC)C2OC2OC(C)C(O)C(O)C2O)C(O)C1O

InChI Identifier

InChI=1S/C68H120O24/c1-9-12-15-17-19-20-24-28-32-37-46(69)86-57-42(6)82-65(55(78)53(57)76)90-59-44(8)84-68(63(88-48(71)39-34-27-22-18-16-13-10-2)62(59)92-64-54(77)51(74)49(72)40(4)80-64)89-58-43(7)83-67-61(56(58)79)87-47(70)38-33-29-25-21-23-26-31-36-45(35-30-14-11-3)85-66-60(91-67)52(75)50(73)41(5)81-66/h40-45,49-68,72-79H,9-39H2,1-8H3

InChI Key

PIPJWVLVHFNOQG-UHFFFAOYSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ipomoea batatas	FooDB	KNAPSACK
Solanum tuberosum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

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
2-furanone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
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	5.01	ALOGPS
logP	11.31	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	11.85	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	333.04 Å²	ChemAxon
Rotatable Bond Count	32	ChemAxon
Refractivity	330.78 m³·mol⁻¹	ChemAxon
Polarizability	148.58 Å³	ChemAxon
Number of Rings	6	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

HMDB0029982

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001269

KNApSAcK ID

Not Available

Chemspider ID

8682451

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10507050

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]

Showing NP-Card for Simonin IV (NP0045501)

MOL for NP0045501 (Simonin IV)

3D MOL for NP0045501 (Simonin IV)

3D SDF for NP0045501 (Simonin IV)

3D-SDF for NP0045501 (Simonin IV)

PDB for NP0045501 (Simonin IV)

3D PDB for NP0045501 (Simonin IV)

SMILES for NP0045501 (Simonin IV)

INCHI for NP0045501 (Simonin IV)

Structure for NP0045501 (Simonin IV)

3D Structure for NP0045501 (Simonin IV)