NP-MRD: Showing NP-Card for (1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate (NP0302157)

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Record Information

Version

2.0

Created at

2022-09-10 15:31:47 UTC

Updated at

2022-09-10 15:31:47 UTC

NP-MRD ID

NP0302157

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(1R,2R,3S,8R,10R,11R,15R,16S)-3-(acetyloxy)-15-[(5S)-5-[(2R)-3,3-dimethyloxiran-2-yl]-2-oxo-2,5-dihydrofuran-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadec-12-en-10-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. (1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate is found in Simarouba amara. Based on a literature review very few articles have been published on (1R,2R,3S,8R,10R,11R,15R,16S)-3-(acetyloxy)-15-[(5S)-5-[(2R)-3,3-dimethyloxiran-2-yl]-2-oxo-2,5-dihydrofuran-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadec-12-en-10-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102217312D          

 43 48  0  0  1  0            999 V2000
    1.8467   -2.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309102217312D          

 43 48  0  0  1  0            999 V2000
    1.8467   -2.5217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -1.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5852   -1.8506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7972   -1.0936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602   -0.3939    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5401   -0.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0417    0.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8211   -0.1694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0530    0.9205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7527    1.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1709    1.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1935    2.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5307    1.0829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0705    1.7068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8807    1.5512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4205    2.1751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502    2.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400    3.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6900    3.5784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510    0.7718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6909    1.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9612    0.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6190    1.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2959    0.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0564   -0.1470    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5544   -0.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793   -0.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6496   -1.5679    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4391   -1.8074    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2425   -1.6200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0031   -2.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6175   -2.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6958   -3.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919   -2.0659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3150   -1.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5356   -1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2316   -0.1633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5819   -0.9102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6918   -0.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8816   -0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6112    0.1479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8010    0.3035    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1289   -0.4536    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  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 28 34  1  0  0  0  0
 34 35  1  0  0  0  0
 26 35  1  0  0  0  0
 35 36  2  0  0  0  0
 25 37  1  0  0  0  0
 22 37  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 41 40  1  6  0  0  0
 20 41  1  0  0  0  0
 41 42  1  0  0  0  0
  5 42  1  0  0  0  0
 13 42  1  0  0  0  0
 42 43  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0302157

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@@H]2[C@@](C)([C@H]3CC[C@@]4(C)[C@@H](CC=C4[C@]13C)C1=C[C@H](OC1=O)[C@H]1OC1(C)C)[C@H](CC(=O)OC2(C)C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H46O9/c1-17(35)39-25-15-24-30(3,4)42-27(37)16-26(40-18(2)36)34(24,9)23-12-13-32(7)20(10-11-22(32)33(23,25)8)19-14-21(41-29(19)38)28-31(5,6)43-28/h11,14,20-21,23-26,28H,10,12-13,15-16H2,1-9H3/t20-,21-,23-,24-,25+,26-,28+,32-,33-,34+/m0/s1

> <INCHI_KEY>
FOXHMXWSLKJAME-DQBNIYBLSA-N

> <FORMULA>
C34H46O9

> <MOLECULAR_WEIGHT>
598.733

> <EXACT_MASS>
598.314183061

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
64.64775894570147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
3.903179601999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.463106165633718

> <JCHEM_PKA_STRONGEST_BASIC>
-4.240866528776635

> <JCHEM_POLAR_SURFACE_AREA>
117.73000000000002

> <JCHEM_REFRACTIVITY>
155.45620000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       3.447  -4.707   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.631  -3.401   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.092  -3.454   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.355  -2.041   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.539  -0.735   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.008  -0.903   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.078   0.188   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.533  -0.316   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.099   1.718   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.405   2.534   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.319   3.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.228   3.836   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.857   2.021   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.865   3.186   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.377   2.896   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.385   4.060   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.880   5.515   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.368   5.805   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.888   6.680   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.882   1.441   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.890   2.605   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.394   1.150   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.622   2.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.886   1.199   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.439  -0.274   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.368  -1.502   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.908  -1.472   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.413  -2.927   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.886  -3.374   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      15.386  -3.024   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.939  -4.498   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.086  -5.526   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.366  -5.927   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.185  -3.856   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.921  -2.976   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.466  -3.481   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.899  -0.305   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.553  -1.699   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.891  -1.469   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.379  -1.179   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.874   0.276   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.362   0.566   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.974  -0.847   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   42                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   42                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   22   41                                             
CONECT   21   20                                                            
CONECT   22   20   23   37                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   37                                                  
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   31                                                       
CONECT   31   30   29   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   28   35                                                       
CONECT   35   34   26   36                                                  
CONECT   36   35                                                            
CONECT   37   25   22   38   39                                             
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   20   42                                                  
CONECT   42   41    5   13   43                                             
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₃₄H₄₆O₉

Average Mass

598.7330 Da

Monoisotopic Mass

598.31418 Da

IUPAC Name

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@@H]2[C@@](C)([C@H]3CC[C@@]4(C)[C@@H](CC=C4[C@]13C)C1=C[C@H](OC1=O)[C@H]1OC1(C)C)[C@H](CC(=O)OC2(C)C)OC(C)=O

InChI Identifier

InChI=1S/C34H46O9/c1-17(35)39-25-15-24-30(3,4)42-27(37)16-26(40-18(2)36)34(24,9)23-12-13-32(7)20(10-11-22(32)33(23,25)8)19-14-21(41-29(19)38)28-31(5,6)43-28/h11,14,20-21,23-26,28H,10,12-13,15-16H2,1-9H3/t20-,21-,23-,24-,25+,26-,28+,32-,33-,34+/m0/s1

InChI Key

FOXHMXWSLKJAME-DQBNIYBLSA-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
Simarouba amara	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
Tetracarboxylic acid or derivatives
Caprolactone
Oxepane
2-furanone
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
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	3.9	ChemAxon
pKa (Strongest Acidic)	11.46	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	117.73 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	155.46 m³·mol⁻¹	ChemAxon
Polarizability	64.65 Å³	ChemAxon
Number of Rings	6	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

163034084

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate (NP0302157)

MOL for NP0302157 ((1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

3D MOL for NP0302157 ((1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

3D SDF for NP0302157 ((1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

3D-SDF for NP0302157 ((1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

PDB for NP0302157 ((1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

3D PDB for NP0302157 ((1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

SMILES for NP0302157 ((1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

INCHI for NP0302157 ((1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

Structure for NP0302157 ((1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

3D Structure for NP0302157 ((1r,2r,3s,8r,10r,11r,15r,16s)-3-(acetyloxy)-15-[(5s)-5-[(2r)-3,3-dimethyloxiran-2-yl]-2-oxo-5h-furan-3-yl]-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)