NP-MRD: Showing NP-Card for (-)-Azadirachtin Q (NP0078327)

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Record Information

Version

2.0

Created at

2022-04-28 23:25:43 UTC

Updated at

2022-04-28 23:25:43 UTC

NP-MRD ID

NP0078327

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Azadirachtin Q

Description

4,11-Dimethyl (1R,4S,5R,6S,7S,8R,11S,12R,14S,15S)-12,14-bis(acetyloxy)-7-hydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]Dodec-3-en-9-yl]-6-methyl-3,9-dioxatetracyclo[6.6.1.0¹,⁵.0¹¹,¹⁵]Pentadecane-4,11-dicarboxylate 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. (-)-Azadirachtin Q is found in Azadirachta excelsa. Based on a literature review very few articles have been published on 4,11-dimethyl (1R,4S,5R,6S,7S,8R,11S,12R,14S,15S)-12,14-bis(acetyloxy)-7-hydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0²,⁶.0⁹,¹¹]Dodec-3-en-9-yl]-6-methyl-3,9-dioxatetracyclo[6.6.1.0¹,⁵.0¹¹,¹⁵]Pentadecane-4,11-dicarboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201252D          

 47 54  0  0  1  0            999 V2000
    2.8841    2.8453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3176    2.1434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.1018    1.3926    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.0595    2.8209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0063    3.6442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4985    4.2944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.4373    5.4471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1 47  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292201252D          

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    3.3176    2.1434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9264    1.4170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1018    1.3926    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6683    2.0945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0595    2.8209    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0063    3.6442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4985    4.2944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6904    5.0968    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4373    5.4471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1769    5.0816    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3522    4.2754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8312    3.6357    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4434    4.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7531    5.6720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3696    6.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5564    6.2635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749    5.9389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7127    4.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1893    3.5296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    3.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8668    1.8992    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8049    1.0765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5011    0.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2376    2.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3851    3.2445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5391    2.1547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1683    2.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107    0.6662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1441   -0.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9688   -0.0113    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3599    0.7151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2398    1.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1293    1.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9405    0.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7233   -0.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7384    0.3388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3190   -0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4023   -0.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0111   -1.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4446   -2.1415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1865   -1.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860    0.6418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4949   -0.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9283   -0.7865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3298   -0.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2753    3.5717    0.0000 O   0  0  0  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
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
  9 14  1  1  0  0  0
 11 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 10 17  1  0  0  0  0
 10 18  1  1  0  0  0
  8 19  1  6  0  0  0
  8 20  1  0  0  0  0
  7 20  1  1  0  0  0
  6 21  1  1  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  4 24  1  6  0  0  0
 22 25  1  6  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  4 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
  3 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  6  0  0  0
 32 35  1  1  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 31 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 29 43  1  6  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 44 46  1  0  0  0  0
  1 47  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0078327

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1OC[C@]23[C@@H]4[C@@H](OC[C@@]4([C@@H](C[C@@H]2OC(C)=O)OC(C)=O)C(=O)OC)[C@@H](O)[C@](C)([C@H]13)[C@]12O[C@@]1(C)[C@H]1C[C@@H]2O[C@@H]2OC=C[C@@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O15/c1-13(33)44-16-10-17(45-14(2)34)30(25(37)40-6)12-42-19-22(30)29(16)11-43-20(24(36)39-5)21(29)27(3,23(19)35)32-18-9-15(28(32,4)47-32)31(38)7-8-41-26(31)46-18/h7-8,15-23,26,35,38H,9-12H2,1-6H3/t15-,16+,17-,18+,19-,20+,21+,22+,23-,26+,27+,28+,29+,30+,31-,32+/m1/s1

> <INCHI_KEY>
WCKRCDIVSWWTJC-MDVWXCEDSA-N

> <FORMULA>
C32H40O15

> <MOLECULAR_WEIGHT>
664.657

> <EXACT_MASS>
664.236720588

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
64.7070485987064

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,11-dimethyl (1R,4S,5R,6S,7S,8R,11S,12R,14S,15S)-12,14-bis(acetyloxy)-7-hydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0^{2,6}.0^{9,11}]dodec-3-en-9-yl]-6-methyl-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecane-4,11-dicarboxylate

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
-1.7521271530000013

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.658090897555372

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.267150598191165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3939928928765264

> <JCHEM_POLAR_SURFACE_AREA>
195.10999999999999

> <JCHEM_REFRACTIVITY>
149.963

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,11-dimethyl (1R,4S,5R,6S,7S,8R,11S,12R,14S,15S)-12,14-bis(acetyloxy)-7-hydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0^{2,6}.0^{9,11}]dodec-3-en-9-yl]-6-methyl-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecane-4,11-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.384   5.311   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.193   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.463   2.645   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.923   2.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.114   3.910   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.844   5.266   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.745   6.802   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.797   8.016   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.155   9.514   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.550  10.168   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.930   9.486   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.257   7.981   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.285   6.787   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.561   8.417   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.006  10.588   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.290  11.951   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.772  11.692   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.313  11.086   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.330   8.485   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.220   6.589   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.515   6.043   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.618   3.545   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.502   2.009   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.802   1.842   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.444   4.541   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.719   6.056   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.006   4.022   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.181   5.018   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.193   1.244   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.002  -0.067   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.542  -0.021   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.272   1.335   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.914   2.199   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.708   3.726   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.356   0.241   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.950  -1.245   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       8.845   0.632   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.929  -0.462   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.351  -1.331   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.621  -2.687   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.430  -3.998   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.081  -2.733   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.654   1.198   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       0.924  -0.158   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       1.733  -1.468   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -0.616  -0.204   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       6.114   6.667   0.000  0.00  0.00           O+0
CONECT    1    2    6   47                                                  
CONECT    2    1    3   34                                                  
CONECT    3    2    4   32                                                  
CONECT    4    3    5   24   29                                             
CONECT    5    4    6   22                                                  
CONECT    6    5    1    7   21                                             
CONECT    7    6    8   13   20                                             
CONECT    8    7    9   19   20                                             
CONECT    9    8   10   14                                                  
CONECT   10    9   11   17   18                                             
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13    9                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10                                                       
CONECT   18   10                                                            
CONECT   19    8                                                            
CONECT   20    8    7                                                       
CONECT   21    6                                                            
CONECT   22    5   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23    4                                                       
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29    4   30   43                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   39                                                  
CONECT   32   31    3   33   35                                             
CONECT   33   32   34                                                       
CONECT   34   33    2                                                       
CONECT   35   32   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37                                                            
CONECT   39   31   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   29   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47    1                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  108    0
END

View in JSmol

Synonyms

Value	Source
4,11-Dimethyl (1R,4S,5R,6S,7S,8R,11S,12R,14S,15S)-12,14-bis(acetyloxy)-7-hydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0,.0,]dodec-3-en-9-yl]-6-methyl-3,9-dioxatetracyclo[6.6.1.0,.0,]pentadecane-4,11-dicarboxylic acid	Generator

Chemical Formula

C₃₂H₄₀O₁₅

Average Mass

664.6570 Da

Monoisotopic Mass

664.23672 Da

IUPAC Name

4,11-dimethyl (1R,4S,5R,6S,7S,8R,11S,12R,14S,15S)-12,14-bis(acetyloxy)-7-hydroxy-6-[(1S,2R,6S,8S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.0^{2,6}.0^{9,11}]dodec-3-en-9-yl]-6-methyl-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecane-4,11-dicarboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1OC[C@]23[C@@H]4[C@@H](OC[C@@]4([C@@H](C[C@@H]2OC(C)=O)OC(C)=O)C(=O)OC)[C@@H](O)[C@](C)([C@H]13)[C@]12O[C@@]1(C)[C@H]1C[C@@H]2O[C@@H]2OC=C[C@@]12O

InChI Identifier

InChI=1S/C32H40O15/c1-13(33)44-16-10-17(45-14(2)34)30(25(37)40-6)12-42-19-22(30)29(16)11-43-20(24(36)39-5)21(29)27(3,23(19)35)32-18-9-15(28(32,4)47-32)31(38)7-8-41-26(31)46-18/h7-8,15-23,26,35,38H,9-12H2,1-6H3/t15-,16+,17-,18+,19-,20+,21+,22+,23-,26+,27+,28+,29+,30+,31-,32+/m1/s1

InChI Key

WCKRCDIVSWWTJC-MDVWXCEDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 excelsa	Plant	KNApSAcK

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
Furopyran
Oxepane
Pyran
Oxane
Methyl ester
Tetrahydrofuran
Tertiary alcohol
Furan
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.93	ALOGPS
logP	-1.8	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.27	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	195.11 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	149.96 m³·mol⁻¹	ChemAxon
Polarizability	64.71 Å³	ChemAxon
Number of Rings	8	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

162933926

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Azadirachtin Q (NP0078327)

MOL for NP0078327 ((-)-Azadirachtin Q)

3D MOL for NP0078327 ((-)-Azadirachtin Q)

3D SDF for NP0078327 ((-)-Azadirachtin Q)

3D-SDF for NP0078327 ((-)-Azadirachtin Q)

PDB for NP0078327 ((-)-Azadirachtin Q)

3D PDB for NP0078327 ((-)-Azadirachtin Q)

SMILES for NP0078327 ((-)-Azadirachtin Q)

INCHI for NP0078327 ((-)-Azadirachtin Q)

Structure for NP0078327 ((-)-Azadirachtin Q)

3D Structure for NP0078327 ((-)-Azadirachtin Q)