NP-MRD: Showing NP-Card for (1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate (NP0143410)

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Record Information

Version

2.0

Created at

2022-09-01 22:09:41 UTC

Updated at

2022-09-01 22:09:41 UTC

NP-MRD ID

NP0143410

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate

Description

(1S,2R,4R,5S,6R,10R,11R,13R,14R,15S,18S,20R)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]Icos-8-en-4-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. (1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate is found in Azadirachta indica. Based on a literature review very few articles have been published on (1S,2R,4R,5S,6R,10R,11R,13R,14R,15S,18S,20R)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]Icos-8-en-4-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022200092D          

 43 48  0  0  1  0            999 V2000
    2.3757   -2.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3230   -1.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5376    0.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1738    1.2749    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3930    1.5412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3402    2.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 41 42  2  0  0  0  0
 43 41  1  6  0  0  0
  8 43  1  0  0  0  0
 23 43  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022200092D          

 43 48  0  0  1  0            999 V2000
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    2.1738    1.2749    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3930    1.5412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3402    2.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6525    1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3862    0.3966    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4371    0.3438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8031   -0.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3457   -1.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6264   -0.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -0.3438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2051   -0.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7954    0.5418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2412   -0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0653   -0.1135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5110   -0.8078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4436    0.6196    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8893   -0.0746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2677    0.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8480    0.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5850    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4602    1.2584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0466    1.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9218    2.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6588    3.0249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2391    2.4385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8607    1.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6460    1.3916    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0989    2.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2003    2.0859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5787    2.8190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1329    3.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3088    3.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5113    4.2463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3762    2.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9305    2.7412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979    1.3138    0.0000 C   0  0  1  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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 12 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 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
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  2  0  0  0  0
 28 34  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  1  6  0  0  0
 34 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
 36 41  1  0  0  0  0
 41 42  2  0  0  0  0
 43 41  1  6  0  0  0
  8 43  1  0  0  0  0
 23 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0143410

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@H](O)[C@@]23CO[C@@H](OC(C)=O)[C@]1(C)[C@@H]2C[C@@H](O)[C@]1(C)[C@H]3C(=O)[C@H](OC(C)=O)[C@@]2(C)[C@@H](CC=C12)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O11/c1-15(33)41-24-12-23(37)32-14-40-28(43-17(3)35)31(24,6)21(32)11-22(36)30(5)20-8-7-19(18-9-10-39-13-18)29(20,4)27(42-16(2)34)25(38)26(30)32/h8-10,13,19,21-24,26-28,36-37H,7,11-12,14H2,1-6H3/t19-,21-,22+,23-,24+,26+,27-,28-,29-,30+,31+,32+/m0/s1

> <INCHI_KEY>
YQSXXKRVYCLMRM-KFKOUZSSSA-N

> <FORMULA>
C32H40O11

> <MOLECULAR_WEIGHT>
600.661

> <EXACT_MASS>
600.257062108

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
61.612585559675765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4R,5S,6R,10R,11R,13R,14R,15S,18S,20R)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0^{1,13}.0^{2,10}.0^{5,9}]icos-8-en-4-yl acetate

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
1.0195662066666673

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.9503158391291

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.862745050312313

> <JCHEM_PKA_STRONGEST_BASIC>
-2.862540150104904

> <JCHEM_POLAR_SURFACE_AREA>
158.8

> <JCHEM_REFRACTIVITY>
147.98409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.69e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5S,6R,10R,11R,13R,14R,15S,18S,20R)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0^{1,13}.0^{2,10}.0^{5,9}]icos-8-en-4-yl acetate

> <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       4.435  -4.896   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.336  -3.359   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.618  -2.505   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.956  -2.676   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.858  -1.139   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.432  -0.851   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.737   0.998   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.058   2.380   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.600   2.877   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.502   4.414   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.218   2.198   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.721   0.740   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.816   0.642   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.499  -0.738   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.645  -2.020   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.036  -0.837   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.400  -0.642   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.383  -1.798   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.351   1.011   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.184  -0.285   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.722  -0.212   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.554  -1.508   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.428   1.157   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.260  -0.139   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.966   1.229   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.050   0.135   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.425   0.827   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.192   2.349   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.287   3.432   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.054   4.954   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.430   5.646   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      13.513   4.552   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.807   3.183   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.673   2.598   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.518   3.885   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.841   3.894   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.547   5.262   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       7.715   6.558   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.177   6.485   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       8.421   7.926   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.302   3.821   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.470   5.117   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       5.596   2.452   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   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19   43                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12    5   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    8   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   43                                             
CONECT   24   23                                                            
CONECT   25   23   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   34                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   29                                                       
CONECT   34   28   25   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   36   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    8   23                                                  
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,4R,5S,6R,10R,11R,13R,14R,15S,18S,20R)-15,20-Bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0,.0,.0,]icos-8-en-4-yl acetic acid	Generator

Chemical Formula

C₃₂H₄₀O₁₁

Average Mass

600.6610 Da

Monoisotopic Mass

600.25706 Da

IUPAC Name

(1S,2R,4R,5S,6R,10R,11R,13R,14R,15S,18S,20R)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0^{1,13}.0^{2,10}.0^{5,9}]icos-8-en-4-yl acetate

Traditional Name

(1S,2R,4R,5S,6R,10R,11R,13R,14R,15S,18S,20R)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0^{1,13}.0^{2,10}.0^{5,9}]icos-8-en-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@H](O)[C@@]23CO[C@@H](OC(C)=O)[C@]1(C)[C@@H]2C[C@@H](O)[C@]1(C)[C@H]3C(=O)[C@H](OC(C)=O)[C@@]2(C)[C@@H](CC=C12)C1=COC=C1

InChI Identifier

InChI=1S/C32H40O11/c1-15(33)41-24-12-23(37)32-14-40-28(43-17(3)35)31(24,6)21(32)11-22(36)30(5)20-8-7-19(18-9-10-39-13-18)29(20,4)27(42-16(2)34)25(38)26(30)32/h8-10,13,19,21-24,26-28,36-37H,7,11-12,14H2,1-6H3/t19-,21-,22+,23-,24+,26+,27-,28-,29-,30+,31+,32+/m0/s1

InChI Key

YQSXXKRVYCLMRM-KFKOUZSSSA-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
Azadirachta indica	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
Hydroxysteroid
1-hydroxysteroid
Steroid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Alpha-acyloxy ketone
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Ketone
Carboxylic acid ester
Secondary alcohol
Oxacycle
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.61	ALOGPS
logP	1.02	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	158.8 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	147.98 m³·mol⁻¹	ChemAxon
Polarizability	61.61 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

163193927

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,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate (NP0143410)

MOL for NP0143410 ((1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate)

3D MOL for NP0143410 ((1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate)

3D SDF for NP0143410 ((1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate)

3D-SDF for NP0143410 ((1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate)

PDB for NP0143410 ((1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate)

3D PDB for NP0143410 ((1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate)

SMILES for NP0143410 ((1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate)

INCHI for NP0143410 ((1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate)

Structure for NP0143410 ((1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate)

3D Structure for NP0143410 ((1s,2r,4r,5s,6s,10r,11r,13r,14r,15s,18s,20r)-15,20-bis(acetyloxy)-6-(furan-3-yl)-11,18-dihydroxy-5,10,14-trimethyl-3-oxo-16-oxapentacyclo[12.3.3.0¹,¹³.0²,¹⁰.0⁵,⁹]icos-8-en-4-yl acetate)