NP-MRD: Showing NP-Card for (1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate (NP0197089)

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Record Information

Version

2.0

Created at

2022-09-04 15:17:23 UTC

Updated at

2022-09-04 15:17:24 UTC

NP-MRD ID

NP0197089

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate

Description

Nimbolinin D 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,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate is found in Melia azedarach. (1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate was first documented in 2017 (PMID: 28145090). Based on a literature review very few articles have been published on Nimbolinin D (PMID: 32148525).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217172D          

 45 51  0  0  1  0            999 V2000
    4.7408    4.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0616    3.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1275    2.8814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4151    2.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964    1.6488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8606    1.0469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3784    0.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830    1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1910    0.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9638   -0.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042217172D          

 45 51  0  0  1  0            999 V2000
    4.7408    4.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0616    3.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1275    2.8814    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4151    2.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964    1.6488    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8606    1.0469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3784    0.4046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6830    1.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1910    0.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9638   -0.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9662    0.7451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6503    0.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6792   -0.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4723   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9335   -0.0838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4255    0.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9373    1.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1442    1.7969    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8970    2.5839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6215    0.2573    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1858   -0.3445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9467   -1.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1434   -1.3219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5110   -1.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143   -1.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8786   -2.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6395   -2.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8361   -3.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2719   -2.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8182    0.0696    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4202   -0.6530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6099   -0.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5072    0.3208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8011   -0.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8301    0.7922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0833    0.4415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5937    0.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3405    0.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5240    1.7350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8998    1.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6466    1.9649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6870    2.7889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930    1.4610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6193    2.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.6714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  2  0  0  0  0
 11 17  1  0  0  0  0
 18 17  1  1  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 20 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 35 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  0  0  0  0
  5 43  1  0  0  0  0
 43 44  1  1  0  0  0
 43 45  1  0  0  0  0
 45 30  1  1  0  0  0
 33 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197089

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@@H]2[C@]3(C)[C@H]4[C@@H](OC[C@]4(C)[C@@H](C[C@@H]3O)OC(C)=O)[C@@H](OC(=O)C3=CC=CC=C3)[C@@]2(C)C2=C(C)[C@@H](C[C@@H]2O1)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C36H44O9/c1-19-23(22-12-13-41-17-22)14-24-29(19)36(5)25(15-28(40-6)44-24)35(4)26(38)16-27(43-20(2)37)34(3)18-42-30(31(34)35)32(36)45-33(39)21-10-8-7-9-11-21/h7-13,17,23-28,30-32,38H,14-16,18H2,1-6H3/t23-,24+,25-,26+,27-,28-,30-,31+,32-,34-,35+,36-/m1/s1

> <INCHI_KEY>
GVCKQCGCUAALBH-ADQQNIAQSA-N

> <FORMULA>
C36H44O9

> <MOLECULAR_WEIGHT>
620.739

> <EXACT_MASS>
620.298532997

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
66.16203425953589

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-12-yl benzoate

> <JCHEM_LOGP>
4.028074067666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.600801380110745

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8289186088156564

> <JCHEM_POLAR_SURFACE_AREA>
113.66000000000001

> <JCHEM_REFRACTIVITY>
163.46460000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-12-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       8.849   7.788   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.582   6.914   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.705   5.379   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.375   4.602   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.153   3.078   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.207   1.954   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.173   0.755   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.742   2.077   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.690   0.864   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.266  -0.617   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.137   1.391   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.414   0.530   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.468  -1.009   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.948  -1.433   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.809  -0.156   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      13.861   1.057   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.083   2.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.603   3.354   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.141   4.823   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.760   0.480   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.814  -0.643   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.367  -2.117   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.868  -2.467   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.420  -3.241   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.920  -2.890   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.973  -4.014   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.527  -5.487   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.027  -5.838   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.974  -4.714   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.261   0.130   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.518  -1.219   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.005  -0.929   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.813   0.599   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.495  -0.198   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.550   1.479   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.156   0.824   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.108   1.704   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.502   1.050   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.978   3.239   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.680   3.013   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.074   3.668   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.149   5.206   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       4.654   2.727   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.889   4.249   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.207   1.253   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   43                                                  
CONECT    6    5    7    8   20                                             
CONECT    7    6                                                            
CONECT    8    6    9   18                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
CONECT   17   11   18                                                       
CONECT   18   17    8   19                                                  
CONECT   19   18    3                                                       
CONECT   20    6   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   20   31   45                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35   45                                             
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   35   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41    5   44   45                                             
CONECT   44   43                                                            
CONECT   45   43   30   33                                                  
MASTER        0    0    0    0    0    0    0    0   45    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₄₄O₉

Average Mass

620.7390 Da

Monoisotopic Mass

620.29853 Da

IUPAC Name

(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-12-yl benzoate

Traditional Name

(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-12-yl benzoate

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@@H]2[C@]3(C)[C@H]4[C@@H](OC[C@]4(C)[C@@H](C[C@@H]3O)OC(C)=O)[C@@H](OC(=O)C3=CC=CC=C3)[C@@]2(C)C2=C(C)[C@@H](C[C@@H]2O1)C1=COC=C1

InChI Identifier

InChI=1S/C36H44O9/c1-19-23(22-12-13-41-17-22)14-24-29(19)36(5)25(15-28(40-6)44-24)35(4)26(38)16-27(43-20(2)37)34(3)18-42-30(31(34)35)32(36)45-33(39)21-10-8-7-9-11-21/h7-13,17,23-28,30-32,38H,14-16,18H2,1-6H3/t23-,24+,25-,26+,27-,28-,30-,31+,32-,34-,35+,36-/m1/s1

InChI Key

GVCKQCGCUAALBH-ADQQNIAQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melia azedarach	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Oxepane
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Heteroaromatic compound
Cyclic alcohol
Furan
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Ether
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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	4.03	ChemAxon
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	113.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	163.46 m³·mol⁻¹	ChemAxon
Polarizability	66.16 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00047794

Chemspider ID

9016869

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10841573

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Akihisa T, Nishimoto Y, Ogihara E, Matsumoto M, Zhang J, Abe M: Nitric Oxide Production-Inhibitory Activity of Limonoids from Azadirachta indica and Melia azedarach. Chem Biodivers. 2017 Jun;14(6). doi: 10.1002/cbdv.201600468. Epub 2017 May 23. [PubMed:28145090 ]
Afagnigni AD, Nyegue MA, Djova SV, Etoa FX: LC-MS Analysis, 15-Lipoxygenase Inhibition, Cytotoxicity, and Genotoxicity of Dissotis multiflora (Sm) Triana (Melastomataceae) and Paullinia pinnata Linn (Sapindaceae). J Trop Med. 2020 Feb 18;2020:5169847. doi: 10.1155/2020/5169847. eCollection 2020. [PubMed:32148525 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate (NP0197089)

MOL for NP0197089 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

3D MOL for NP0197089 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

3D SDF for NP0197089 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

3D-SDF for NP0197089 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

PDB for NP0197089 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

3D PDB for NP0197089 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

SMILES for NP0197089 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

INCHI for NP0197089 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

Structure for NP0197089 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

3D Structure for NP0197089 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17-(acetyloxy)-8-(furan-3-yl)-19-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)