NP-MRD: Showing NP-Card for (2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate (NP0285650)

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Record Information

Version

2.0

Created at

2022-09-09 13:54:45 UTC

Updated at

2022-09-09 13:54:45 UTC

NP-MRD ID

NP0285650

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate

Description

(1S,2S,3R,8S,10S,11S,15R,16R)-15-[(2S,3R,5S)-2-(acetyloxy)-5-(2-methylprop-1-en-1-yl)oxolan-3-yl]-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadec-12-en-3-yl acetate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Based on a literature review very few articles have been published on (1S,2S,3R,8S,10S,11S,15R,16R)-15-[(2S,3R,5S)-2-(acetyloxy)-5-(2-methylprop-1-en-1-yl)oxolan-3-yl]-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadec-12-en-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092215542D          

 42 46  0  0  1  0            999 V2000
    3.8892   -6.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1098   -5.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4859   -6.4176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -5.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748   -4.7972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4979   -5.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401   -4.7709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0506   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514   -4.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3409   -4.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3640   -3.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -3.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353   -4.0077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4333   -3.3499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1939   -2.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8708   -2.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5285   -2.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3387   -2.4312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7989   -1.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6091   -1.6517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0692   -1.0279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4193   -1.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3188   -1.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5314   -3.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7980   -3.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2582   -3.3662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9078   -4.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
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 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 17 41  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  1  1  0  0  0
M  END

     RDKit          3D

 92 96  0  0  0  0  0  0  0  0999 V2000
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    4.0020    0.4222    0.6981 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309092215542D          

 42 46  0  0  1  0            999 V2000
    3.8892   -6.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1098   -5.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4859   -6.4176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9542   -5.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1748   -4.7972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4979   -5.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8401   -4.7709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0506   -5.0103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514   -4.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3409   -4.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3640   -3.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105   -3.9914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9353   -4.0077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4333   -3.3499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1939   -2.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8708   -2.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5285   -2.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3387   -2.4312    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7989   -1.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6091   -1.6517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0692   -1.0279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4193   -1.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9591   -2.1200    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7371   -1.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2962   -1.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3188   -1.2604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4368   -2.2824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5314   -3.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3109   -3.3723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9496   -3.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1296   -3.5968    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6926   -4.2965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0800   -5.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9045   -5.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6430   -5.7246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6888   -2.8994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3609   -3.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8786   -3.0550    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6082   -3.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7980   -3.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2582   -3.3662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9078   -4.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 31 36  1  0  0  0  0
 23 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 18 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 17 41  1  0  0  0  0
 14 41  1  0  0  0  0
 41 42  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0285650

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1O[C@@H](C[C@@H]1[C@H]1CC=C2[C@]1(C)CC[C@H]1[C@@]3(C)[C@H](C[C@H](O)[C@]21C)C(C)(C)OC(=O)C[C@H]3OC(C)=O)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C34H50O8/c1-18(2)14-21-15-22(30(41-21)40-20(4)36)23-10-11-24-32(23,7)13-12-25-33(24,8)27(37)16-26-31(5,6)42-29(38)17-28(34(25,26)9)39-19(3)35/h11,14,21-23,25-28,30,37H,10,12-13,15-17H2,1-9H3/t21-,22-,23-,25-,26-,27+,28-,30-,32-,33-,34+/m1/s1

> <INCHI_KEY>
KARYHQFKNHLQCX-RUILWMFDSA-N

> <FORMULA>
C34H50O8

> <MOLECULAR_WEIGHT>
586.766

> <EXACT_MASS>
586.35056857

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
92

> <JCHEM_AVERAGE_POLARIZABILITY>
65.24401623179659

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,5S)-3-[(1S,2S,3R,8S,10S,11S,15R,16R)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate

> <JCHEM_LOGP>
4.210586355666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.623872398440326

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9633182129222

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
157.27840000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,5S)-3-[(1S,2S,3R,8S,10S,11S,15R,16R)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       7.260 -11.476   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.805 -10.972   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.640 -11.979   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.515  -9.459   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.060  -8.955   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.796  -9.835   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.568  -8.906   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.095  -9.353   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.029  -8.300   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.503  -8.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.680  -6.800   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.073  -7.451   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.613  -7.481   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.542  -6.253   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.095  -4.779   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.359  -3.899   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.587  -4.829   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.099  -4.538   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.091  -3.374   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.604  -3.083   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.596  -1.919   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.116  -2.793   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.124  -3.957   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.576  -3.445   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.753  -2.143   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.662  -2.353   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.882  -4.261   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.059  -5.790   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      15.514  -6.295   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.973  -6.882   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.442  -6.714   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.626  -8.020   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.349  -9.380   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.888  -9.433   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.534 -10.686   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.619  -5.412   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.007  -6.825   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.107  -5.703   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.602  -7.158   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.090  -7.448   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.082  -6.284   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.428  -7.678   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12    5   14                                                  
CONECT   14   13   15   41                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   41                                                  
CONECT   18   17   19   20   38                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   36                                                  
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31   23   37   38                                             
CONECT   37   36                                                            
CONECT   38   36   18   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   17   14   42                                             
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,3R,8S,10S,11S,15R,16R)-15-[(2S,3R,5S)-2-(Acetyloxy)-5-(2-methylprop-1-en-1-yl)oxolan-3-yl]-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0,.0,]octadec-12-en-3-yl acetic acid	Generator

Chemical Formula

C₃₄H₅₀O₈

Average Mass

586.7660 Da

Monoisotopic Mass

586.35057 Da

IUPAC Name

(2S,3R,5S)-3-[(1S,2S,3R,8S,10S,11S,15R,16R)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1O[C@@H](C[C@@H]1[C@H]1CC=C2[C@]1(C)CC[C@H]1[C@@]3(C)[C@H](C[C@H](O)[C@]21C)C(C)(C)OC(=O)C[C@H]3OC(C)=O)C=C(C)C

InChI Identifier

InChI=1S/C34H50O8/c1-18(2)14-21-15-22(30(41-21)40-20(4)36)23-10-11-24-32(23,7)13-12-25-33(24,8)27(37)16-26-31(5,6)42-29(38)17-28(34(25,26)9)39-19(3)35/h11,14,21-23,25-28,30,37H,10,12-13,15-17H2,1-9H3/t21-,22-,23-,25-,26-,27+,28-,30-,32-,33-,34+/m1/s1

InChI Key

KARYHQFKNHLQCX-RUILWMFDSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Tricarboxylic acid or derivatives
Caprolactone
Oxepane
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	4.21	ChemAxon
pKa (Strongest Acidic)	14.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	157.28 m³·mol⁻¹	ChemAxon
Polarizability	65.24 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

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PubChem Compound

163189099

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References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate (NP0285650)

MOL for NP0285650 ((2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate)

3D MOL for NP0285650 ((2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate)

3D SDF for NP0285650 ((2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate)

3D-SDF for NP0285650 ((2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate)

PDB for NP0285650 ((2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate)

3D PDB for NP0285650 ((2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate)

SMILES for NP0285650 ((2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate)

INCHI for NP0285650 ((2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate)

Structure for NP0285650 ((2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate)

3D Structure for NP0285650 ((2s,3r,5s)-3-[(1s,2s,3r,8s,10s,11s,15r,16r)-3-(acetyloxy)-10-hydroxy-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-15-yl]-5-(2-methylprop-1-en-1-yl)oxolan-2-yl acetate)