NP-MRD: Showing NP-Card for 4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate (NP0163616)

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Record Information

Version

2.0

Created at

2022-09-02 22:18:39 UTC

Updated at

2022-09-02 22:18:39 UTC

NP-MRD ID

NP0163616

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate

Description

3,9-Bis(acetyloxy)-2,6,6,10,15-pentamethyl-14-(5-oxooxolan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-11-en-5-yl benzoate 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. 4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate is found in Melia volkensii. Based on a literature review very few articles have been published on 3,9-bis(acetyloxy)-2,6,6,10,15-pentamethyl-14-(5-oxooxolan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-11-en-5-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032200182D          

 45 50  0  0  0  0            999 V2000
    2.0296   -4.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -4.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736   -5.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220   -3.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182   -3.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793   -3.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4023   -3.0335    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
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 13 14  2  0  0  0  0
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 34 44  1  0  0  0  0
  5 44  1  0  0  0  0
 29 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END

     RDKit          3D

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 39 87  1  0
 39 88  1  0
 43 89  1  0
 43 90  1  0
 28 71  1  0
 28 72  1  0
 28 73  1  0
M  END


  Mrv1652309032200182D          

 45 50  0  0  0  0            999 V2000
    2.0296   -4.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -4.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736   -5.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1220   -3.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -2.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182   -3.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793   -3.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976   -2.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416   -1.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613   -0.9463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2537   -1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5340   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3461   -2.7886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8779   -2.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5976   -1.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7855   -1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -1.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -0.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7433    0.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0235    0.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0689   -0.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266   -1.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1912    0.1213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -3.0335    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 22 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 32 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 38 43  1  0  0  0  0
 34 44  1  0  0  0  0
  5 44  1  0  0  0  0
 29 44  1  0  0  0  0
 44 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163616

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC(OC(=O)C2=CC=CC=C2)C(C)(C)C2CC(OC(C)=O)C3(C)C(CCC4(C)C(CC=C34)C3COC(=O)C3)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C37H48O8/c1-21(38)43-30-18-28-34(3,4)29(45-33(41)23-11-9-8-10-12-23)19-31(44-22(2)39)37(28,7)27-15-16-35(5)25(24-17-32(40)42-20-24)13-14-26(35)36(27,30)6/h8-12,14,24-25,27-31H,13,15-20H2,1-7H3

> <INCHI_KEY>
UMDZHCRPOCMGPU-UHFFFAOYSA-N

> <FORMULA>
C37H48O8

> <MOLECULAR_WEIGHT>
620.783

> <EXACT_MASS>
620.334918506

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
68.48269845540878

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,9-bis(acetyloxy)-2,6,6,10,15-pentamethyl-14-(5-oxooxolan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl benzoate

> <ALOGPS_LOGP>
6.17

> <JCHEM_LOGP>
5.363823738000001

> <ALOGPS_LOGS>
-6.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.381083364242368

> <JCHEM_POLAR_SURFACE_AREA>
105.20000000000002

> <JCHEM_REFRACTIVITY>
166.74700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.49e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,9-bis(acetyloxy)-2,6,6,10,15-pentamethyl-14-(5-oxooxolan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl benzoate

> <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       3.789  -8.830   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.305  -8.559   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.297  -9.737   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.828  -7.111   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.341  -6.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.521  -6.072   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.691  -3.215   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.168  -1.766   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.207  -3.486   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.730  -4.934   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.246  -5.205   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.239  -4.028   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.716  -2.580   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.200  -2.309   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.380  -0.953   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.387   0.224   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.911   1.672   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.129  -0.047   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      10.728   0.744   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      11.944  -0.202   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      13.424   0.226   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.351  -5.663   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   44                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   11   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22    7   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30   44                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   37                                             
CONECT   33   32                                                            
CONECT   34   32   35   44                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32   38                                                  
CONECT   38   37   39   43                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   38                                                       
CONECT   44   34    5   29   45                                             
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Value	Source
3,9-Bis(acetyloxy)-2,6,6,10,15-pentamethyl-14-(5-oxooxolan-3-yl)tetracyclo[8.7.0.0,.0,]heptadec-11-en-5-yl benzoic acid	Generator

Chemical Formula

C₃₇H₄₈O₈

Average Mass

620.7830 Da

Monoisotopic Mass

620.33492 Da

IUPAC Name

3,9-bis(acetyloxy)-2,6,6,10,15-pentamethyl-14-(5-oxooxolan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl benzoate

Traditional Name

3,9-bis(acetyloxy)-2,6,6,10,15-pentamethyl-14-(5-oxooxolan-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-11-en-5-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC(OC(=O)C2=CC=CC=C2)C(C)(C)C2CC(OC(C)=O)C3(C)C(CCC4(C)C(CC=C34)C3COC(=O)C3)C12C

InChI Identifier

InChI=1S/C37H48O8/c1-21(38)43-30-18-28-34(3,4)29(45-33(41)23-11-9-8-10-12-23)19-31(44-22(2)39)37(28,7)27-15-16-35(5)25(24-17-32(40)42-20-24)13-14-26(35)36(27,30)6/h8-12,14,24-25,27-31H,13,15-20H2,1-7H3

InChI Key

UMDZHCRPOCMGPU-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, 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 volkensii	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
Steroid ester
Steroid
Tetracarboxylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	6.17	ALOGPS
logP	5.36	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.2 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	166.75 m³·mol⁻¹	ChemAxon
Polarizability	68.48 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

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

73797338

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate (NP0163616)

MOL for NP0163616 (4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

3D MOL for NP0163616 (4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

3D SDF for NP0163616 (4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

3D-SDF for NP0163616 (4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

PDB for NP0163616 (4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

3D PDB for NP0163616 (4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

SMILES for NP0163616 (4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

INCHI for NP0163616 (4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

Structure for NP0163616 (4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)

3D Structure for NP0163616 (4,9-bis(acetyloxy)-3b,6,6,9a,11a-pentamethyl-1-(5-oxooxolan-3-yl)-1h,2h,4h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl benzoate)