NP-MRD: Showing NP-Card for methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate (NP0165375)

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Record Information

Version

2.0

Created at

2022-09-03 00:29:44 UTC

Updated at

2022-09-03 00:29:44 UTC

NP-MRD ID

NP0165375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate

Description

Methyl 2-[(1R,2S,5S,6S,13S,14R,15R,17S,18R)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadec-10-en-18-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. methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate is found in Xylocarpus moluccensis. Based on a literature review very few articles have been published on methyl 2-[(1R,2S,5S,6S,13S,14R,15R,17S,18R)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadec-10-en-18-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032202292D          

 40 45  0  0  1  0            999 V2000
   -3.5322    0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612    1.1828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1214    0.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525   -0.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3504    0.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7106    0.4349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6234   -0.3973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4104   -0.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2127    0.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3742   -0.1959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1890   -0.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6184   -0.9649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7560   -1.7783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5292   -2.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4677   -0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9523   -1.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5405    2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0519    3.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5585    1.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721    0.5201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3692    0.5431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3385    1.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1964   -1.1693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5251   -1.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0342   -2.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3630   -3.3457    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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
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 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 23 29  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 33 32  1  6  0  0  0
 17 33  1  0  0  0  0
 33 34  1  0  0  0  0
  6 34  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  1  0  0  0
 12 36  1  0  0  0  0
  7 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
M  END

     RDKit          2D

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 36 73  1  6
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 28 61  1  0
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M  END


  Mrv1652309032202292D          

 40 45  0  0  1  0            999 V2000
   -3.5322    0.8892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7612    1.1828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6234   -0.3973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.7118    0.9368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9981    1.7106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5405    2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0519    3.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8256    2.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7924    1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8986    0.7979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1849    1.5716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    1.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5585    1.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2721    0.5201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3692    0.5431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3385    1.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1964   -1.1693    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5251   -1.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0342   -2.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7855   -2.4954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3630   -3.3457    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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 23 29  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 33 32  1  6  0  0  0
 17 33  1  0  0  0  0
 33 34  1  0  0  0  0
  6 34  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  1  0  0  0
 12 36  1  0  0  0  0
  7 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0165375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@@H]1[C@@]2(C)C[C@]3(O)[C@@]1(C)[C@@H]1CC[C@]4(C)[C@H](OC(=O)CC4=C1C(=O)[C@]3(OC)[C@@H]2OC(C)=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O10/c1-15(31)39-25-27(3)14-29(35)28(4,19(27)12-20(32)36-5)17-7-9-26(2)18(22(17)23(34)30(25,29)37-6)11-21(33)40-24(26)16-8-10-38-13-16/h8,10,13,17,19,24-25,35H,7,9,11-12,14H2,1-6H3/t17-,19-,24-,25-,26+,27-,28+,29+,30+/m1/s1

> <INCHI_KEY>
DXAWUJPEJQPCGT-KLVFIXQJSA-N

> <FORMULA>
C30H36O10

> <MOLECULAR_WEIGHT>
556.608

> <EXACT_MASS>
556.230847359

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
40.69211033168567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1R,2S,5S,6S,13S,14R,15R,17S,18R)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadec-10-en-18-yl]acetate

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
1.9053032243333314

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.032289801054016

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8698095051268915

> <JCHEM_POLAR_SURFACE_AREA>
138.57000000000002

> <JCHEM_REFRACTIVITY>
137.3315

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,2S,5S,6S,13S,14R,15R,17S,18R)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadec-10-en-18-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.593   1.660   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.154   2.208   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.960   1.236   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.205  -0.285   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.521   1.784   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.326   0.812   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.164  -0.742   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.633  -1.204   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.397   0.804   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.698  -0.366   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.220  -0.125   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.154  -1.801   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.411  -3.320   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.855  -3.856   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.740  -1.659   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.644  -2.905   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.358  -0.214   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.876   0.045   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.860  -1.140   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.378  -0.881   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.361  -2.066   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.912   0.564   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.929   1.749   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.463   3.193   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.609   4.474   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.563   5.683   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.008   5.148   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.946   3.610   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.411   1.489   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.945   2.934   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.427   2.674   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.909   2.415   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.375   0.971   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.689   1.014   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.632   2.553   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.367  -2.183   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.980  -3.595   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.064  -4.833   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.466  -4.658   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.678  -6.245   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8    9   36                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   34                                             
CONECT   11   10                                                            
CONECT   12   10   13   15   36                                             
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   33                                                  
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   23   18   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   17   34                                                  
CONECT   34   33    6   10   35                                             
CONECT   35   34                                                            
CONECT   36   12    7   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(1R,2S,5S,6S,13S,14R,15R,17S,18R)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0,.0,.0,]octadec-10-en-18-yl]acetic acid	Generator

Chemical Formula

C₃₀H₃₆O₁₀

Average Mass

556.6080 Da

Monoisotopic Mass

556.23085 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@@H]1[C@@]2(C)C[C@]3(O)[C@@]1(C)[C@@H]1CC[C@]4(C)[C@H](OC(=O)CC4=C1C(=O)[C@]3(OC)[C@@H]2OC(C)=O)C1=COC=C1

InChI Identifier

InChI=1S/C30H36O10/c1-15(31)39-25-27(3)14-29(35)28(4,19(27)12-20(32)36-5)17-7-9-26(2)18(22(17)23(34)30(25,29)37-6)11-21(33)40-24(26)16-8-10-38-13-16/h8,10,13,17,19,24-25,35H,7,9,11-12,14H2,1-6H3/t17-,19-,24-,25-,26+,27-,28+,29+,30+/m1/s1

InChI Key

DXAWUJPEJQPCGT-KLVFIXQJSA-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
Xylocarpus moluccensis	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

Mexicanolide
Limonoid skeleton
Prostaglandin skeleton
Steroid lactone
Eicosanoid
2-oxosteroid
Oxosteroid
11-oxosteroid
Steroid
3-oxasteroid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Fatty acyl
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Methyl ester
Tertiary alcohol
Lactone
Ketone
Carboxylic acid ester
Ether
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
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	2.71	ALOGPS
logS	-3.8	ALOGPS

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

163060596

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate (NP0165375)

MOL for NP0165375 (methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

3D MOL for NP0165375 (methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

3D SDF for NP0165375 (methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

3D-SDF for NP0165375 (methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

PDB for NP0165375 (methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

3D PDB for NP0165375 (methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

SMILES for NP0165375 (methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

INCHI for NP0165375 (methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

Structure for NP0165375 (methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

3D Structure for NP0165375 (methyl 2-[(1r,2s,5s,6s,13s,14r,15r,17s,18r)-14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)