NP-MRD: Showing NP-Card for (1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate (NP0153327)

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Record Information

Version

2.0

Created at

2022-09-02 09:57:41 UTC

Updated at

2022-09-02 09:57:41 UTC

NP-MRD ID

NP0153327

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate

Description

(1S,2R,5S,6R,8R,10R,11S,12R,14R,15R,16R,19R,20R,21S)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]Henicosan-16-yl (2R)-2-methylbutanoate 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. (1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate is found in Melia azedarach. Based on a literature review very few articles have been published on (1S,2R,5S,6R,8R,10R,11S,12R,14R,15R,16R,19R,20R,21S)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]Henicosan-16-yl (2R)-2-methylbutanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211572D          

 44 50  0  0  1  0            999 V2000
    5.2662    5.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3098    4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6181    3.8463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8828    4.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6616    3.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3969    2.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9699    2.5728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135    1.7489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0825    1.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9940    0.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  5  7  1  0  0  0  0
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 33 44  1  0  0  0  0
 27 44  1  0  0  0  0
M  END

     RDKit          3D

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 41 87  1  0
 42 88  1  6
 40 85  1  0
 38 84  1  0
 37 83  1  0
M  END


  Mrv1652309022211572D          

 44 50  0  0  1  0            999 V2000
    5.2662    5.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3098    4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6181    3.8463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8828    4.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6616    3.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3969    2.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9699    2.5728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135    1.7489    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0825    1.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9940    0.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3495   -0.1288    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1273   -0.4039    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1708   -1.2277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8718   -0.0484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4851   -0.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2696   -0.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4408    0.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8830   -0.8966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1468    0.7294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9706    0.7730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7913    1.4739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3430    2.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8700    0.8528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2981    1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4736    1.2695    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0356    1.9686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    0.5406    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8866    1.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -0.1585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1385   -0.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5764   -1.5866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140   -0.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761   -0.2179    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4155   -0.9024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0635   -0.0756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5294   -0.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4137   -1.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1548   -1.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7285   -1.2358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3420   -0.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0522    0.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6889    1.1038    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4891    1.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2626    0.5109    0.0000 C   0  0  2  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  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  2  0  0  0  0
 30 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  6  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 36 40  2  0  0  0  0
 35 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 44 43  1  1  0  0  0
 42 44  1  0  0  0  0
 33 44  1  0  0  0  0
 27 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153327

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](C)C(=O)O[C@H]1OC[C@]23[C@@H](O)[C@@H](OC(C)=O)[C@@H](O)[C@@]1(C)[C@@H]2C[C@@H](O)[C@]1(C)[C@@H]3C(=O)C[C@@]2(C)[C@@H](C[C@H]3O[C@@]123)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H44O11/c1-7-15(2)27(39)43-28-30(5)20-11-21(36)31(6)24(32(20,14-41-28)26(38)23(25(30)37)42-16(3)34)19(35)12-29(4)18(17-8-9-40-13-17)10-22-33(29,31)44-22/h8-9,13,15,18,20-26,28,36-38H,7,10-12,14H2,1-6H3/t15-,18+,20+,21-,22-,23+,24+,25-,26+,28-,29+,30-,31-,32+,33-/m1/s1

> <INCHI_KEY>
GXRJHIFVOGNSHF-NFVPAXSTSA-N

> <FORMULA>
C33H44O11

> <MOLECULAR_WEIGHT>
616.704

> <EXACT_MASS>
616.288362237

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
64.28238106011112

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,6R,8R,10R,11S,12R,14R,15R,16R,19R,20R,21S)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}.0^{8,10}]henicosan-16-yl (2R)-2-methylbutanoate

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
1.7803825079999989

> <ALOGPS_LOGS>
-3.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.553492925018428

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.622294720557647

> <JCHEM_PKA_STRONGEST_BASIC>
-2.844417938819497

> <JCHEM_POLAR_SURFACE_AREA>
165.26000000000002

> <JCHEM_REFRACTIVITY>
150.76939999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,6R,8R,10R,11S,12R,14R,15R,16R,19R,20R,21S)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0^{1,14}.0^{2,11}.0^{5,10}.0^{8,10}]henicosan-16-yl (2R)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       9.830   9.557   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.912   8.019   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.620   7.180   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.248   7.878   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.702   5.642   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.074   4.943   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.411   4.803   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       7.492   3.265   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.754   2.863   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.589   1.149   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.252  -0.241   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.704  -0.754   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.786  -2.292   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.094  -0.090   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.239  -1.120   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.703  -0.644   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.023   0.863   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.848  -1.674   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.607   1.362   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.145   1.443   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.944   2.751   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.974   3.896   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.224   1.592   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.156   2.425   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.617   2.370   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.800   3.675   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.896   1.009   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.522   2.503   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.713  -0.296   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.992  -1.656   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.809  -2.962   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.453  -1.712   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.635  -0.407   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.776  -1.684   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.118  -0.141   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.988  -1.212   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.772  -2.737   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.156  -3.413   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -3.227  -2.307   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -2.505  -0.946   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.098   1.384   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.286   2.060   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.780   2.435   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       2.357   0.954   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   23   29                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    8   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   11   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   44                                             
CONECT   28   27                                                            
CONECT   29   27   11   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35   44                                             
CONECT   34   33                                                            
CONECT   35   33   36   41                                                  
CONECT   36   35   37   40                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   36                                                       
CONECT   41   35   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42   44                                                       
CONECT   44   43   42   33   27                                             
MASTER        0    0    0    0    0    0    0    0   44    0  100    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,5S,6R,8R,10R,11S,12R,14R,15R,16R,19R,20R,21S)-20-(Acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0,.0,.0,.0,]henicosan-16-yl (2R)-2-methylbutanoic acid	Generator

Chemical Formula

C₃₃H₄₄O₁₁

Average Mass

616.7040 Da

Monoisotopic Mass

616.28836 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@H](C)C(=O)O[C@H]1OC[C@]23[C@@H](O)[C@@H](OC(C)=O)[C@@H](O)[C@@]1(C)[C@@H]2C[C@@H](O)[C@]1(C)[C@@H]3C(=O)C[C@@]2(C)[C@@H](C[C@H]3O[C@@]123)C1=COC=C1

InChI Identifier

InChI=1S/C33H44O11/c1-7-15(2)27(39)43-28-30(5)20-11-21(36)31(6)24(32(20,14-41-28)26(38)23(25(30)37)42-16(3)34)19(35)12-29(4)18(17-8-9-40-13-17)10-22-33(29,31)44-22/h8-9,13,15,18,20-26,28,36-38H,7,10-12,14H2,1-6H3/t15-,18+,20+,21-,22-,23+,24+,25-,26+,28-,29+,30-,31-,32+,33-/m1/s1

InChI Key

GXRJHIFVOGNSHF-NFVPAXSTSA-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
Melia azedarach	LOTUS Database	35616633

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
17-furanylsteroid skeleton
Steroid ester
Naphthopyran
Naphthalene
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Ketone
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Ether
Oxirane
Carboxylic acid derivative
Dialkyl ether
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.48	ALOGPS
logP	1.78	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	12.62	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.26 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	150.77 m³·mol⁻¹	ChemAxon
Polarizability	64.28 Å³	ChemAxon
Number of Rings	7	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

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163185322

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate (NP0153327)

MOL for NP0153327 ((1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate)

3D MOL for NP0153327 ((1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate)

3D SDF for NP0153327 ((1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate)

3D-SDF for NP0153327 ((1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate)

PDB for NP0153327 ((1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate)

3D PDB for NP0153327 ((1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate)

SMILES for NP0153327 ((1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate)

INCHI for NP0153327 ((1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate)

Structure for NP0153327 ((1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate)

3D Structure for NP0153327 ((1s,2r,5s,6s,8r,10r,11s,12r,14r,15r,16r,19r,20r,21s)-20-(acetyloxy)-6-(furan-3-yl)-12,19,21-trihydroxy-5,11,15-trimethyl-3-oxo-9,17-dioxahexacyclo[13.3.3.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0⁸,¹⁰]henicosan-16-yl (2r)-2-methylbutanoate)