NP-MRD: Showing NP-Card for Azadirachtin B (NP0078323)

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Record Information

Version

2.0

Created at

2022-04-28 23:25:25 UTC

Updated at

2022-04-28 23:25:26 UTC

NP-MRD ID

NP0078323

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Azadirachtin B

Description

Azadirachtin B 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 B is found in Azadirachta indica and Zadirachta excelsa. Azadirachtin B was first documented in 2003 (PMID: 12822931). Based on a literature review a significant number of articles have been published on azadirachtin B (PMID: 16752388) (PMID: 16038546) (PMID: 29312880) (PMID: 27317644) (PMID: 19844073) (PMID: 17428489).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201252D          

 51 58  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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  1 54  1  0
 13 63  1  0
 13 64  1  0
 13 65  1  0
 19 66  1  0
 19 67  1  0
 19 68  1  0
 23 72  1  1
 24 73  1  0
 26 74  1  0
 26 75  1  0
 26 76  1  0
 41 88  1  6
 30 77  1  0
 30 78  1  0
 30 79  1  0
 31 80  1  6
 32 81  1  0
 32 82  1  0
 33 83  1  1
 35 84  1  1
 37 85  1  0
 38 86  1  0
 40 87  1  0
M  END


  Mrv1652304292201252D          

 51 58  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
    2.9264    1.4170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1018    1.3926    0.0000 C   0  0  2  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
    2.4261    4.3544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1326    5.1254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3468    5.3767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6604    4.9189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5903    4.0969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1893    3.5296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4614    4.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0130    5.4303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2992    6.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1235    6.1709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9404    5.9496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730    4.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8312    3.6357    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
    0.0567    2.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2133    2.8348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835    1.4317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2936    1.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5806    2.6729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107    0.6662    0.0000 C   0  0  1  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
   -0.7209   -0.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5456   -0.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7633    0.5929    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  1  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  6  0  0  0
  9 14  1  6  0  0  0
 11 15  1  6  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  1  0  0  0
  8 20  1  0  0  0  0
  7 20  1  6  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  1  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
 22 29  1  1  0  0  0
  4 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  6  0  0  0
 33 36  1  1  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 32 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 30 44  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 47 50  1  0  0  0  0
  1 51  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0078323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(O)OC[C@@]23[C@H]4[C@@H](OC[C@@]4([C@@H](C[C@H]2OC(=O)C(\C)=C\C)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/C35H44O16/c1-8-15(2)24(38)49-18-12-19(48-16(3)36)32(26(39)43-6)13-46-21-22(32)31(18)14-47-34(42,27(40)44-7)25(31)29(4,23(21)37)35-20-11-17(30(35,5)51-35)33(41)9-10-45-28(33)50-20/h8-10,17-23,25,28,37,41-42H,11-14H2,1-7H3/b15-8+/t17-,18-,19-,20+,21-,22-,23-,25+,28+,29-,30+,31+,32+,33+,34+,35+/m1/s1

> <INCHI_KEY>
FTNJWQUOZFUQQJ-UZTPERQESA-N

> <FORMULA>
C35H44O16

> <MOLECULAR_WEIGHT>
720.721

> <EXACT_MASS>
720.262935337

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
70.66151319349565

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,11-dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14R,15R)-12-(acetyloxy)-4,7-dihydroxy-6-[(1S,2S,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-14-{[(2E)-2-methylbut-2-enoyl]oxy}-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecane-4,11-dicarboxylate

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
-0.13216088566666798

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.267823359991683

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.42915769108851

> <JCHEM_PKA_STRONGEST_BASIC>
-3.396151453593199

> <JCHEM_POLAR_SURFACE_AREA>
215.33999999999997

> <JCHEM_REFRACTIVITY>
166.23890000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,11-dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14R,15R)-12-(acetyloxy)-4,7-dihydroxy-6-[(1S,2S,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-14-{[(2E)-2-methylbut-2-enoyl]oxy}-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       4.529   8.128   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.981   9.567   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.514  10.036   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.233   9.182   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.102   7.648   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.220   6.589   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.728   8.298   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.024  10.137   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.559  11.581   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.097  11.519   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.622  11.106   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.923   8.782   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.285   6.787   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       0.106   3.836   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.398   5.292   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.903   2.672   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.415   2.964   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.084   4.989   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.193   1.244   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.002  -0.067   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.542  -0.021   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.272   1.335   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.914   2.199   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.708   3.726   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.356   0.241   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.950  -1.245   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       8.845   0.632   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.929  -0.462   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       6.351  -1.331   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.621  -2.687   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       6.430  -3.998   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       4.081  -2.733   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       1.654   1.198   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       0.924  -0.158   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       1.733  -1.468   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -0.616  -0.204   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -1.346  -1.559   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -2.885  -1.605   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -1.425   1.107   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       6.114   6.667   0.000  0.00  0.00           O+0
CONECT    1    2    6   51                                                  
CONECT    2    1    3   35                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3    5   24   30                                             
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   29                                             
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   22                                                            
CONECT   30    4   31   44                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   40                                                  
CONECT   33   32    3   34   36                                             
CONECT   34   33   35                                                       
CONECT   35   34    2                                                       
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   32   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   30   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   50                                                  
CONECT   48   47   49                                                       
CONECT   49   48                                                            
CONECT   50   47                                                            
CONECT   51    1                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₄₄O₁₆

Average Mass

720.7210 Da

Monoisotopic Mass

720.26294 Da

IUPAC Name

4,11-dimethyl (1S,4S,5R,6S,7S,8R,11S,12R,14R,15R)-12-(acetyloxy)-4,7-dihydroxy-6-[(1S,2S,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-14-{[(2E)-2-methylbut-2-enoyl]oxy}-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@@]1(O)OC[C@@]23[C@H]4[C@@H](OC[C@@]4([C@@H](C[C@H]2OC(=O)C(\C)=C\C)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/C35H44O16/c1-8-15(2)24(38)49-18-12-19(48-16(3)36)32(26(39)43-6)13-46-21-22(32)31(18)14-47-34(42,27(40)44-7)25(31)29(4,23(21)37)35-20-11-17(30(35,5)51-35)33(41)9-10-45-28(33)50-20/h8-10,17-23,25,28,37,41-42H,11-14H2,1-7H3/b15-8+/t17-,18-,19-,20+,21-,22-,23-,25+,28+,29-,30+,31+,32+,33+,34+,35+/m1/s1

InChI Key

FTNJWQUOZFUQQJ-UZTPERQESA-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 indica	Plant	KNApSAcK
Zadirachta excelsa	-	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
Fatty acid ester
Oxepane
Oxane
Fatty acyl
Pyran
Cyclic alcohol
Dihydrofuran
Furan
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Enoate ester
Tetrahydrofuran
Methyl ester
Hemiacetal
Carboxylic acid ester
Secondary alcohol
Dialkyl ether
Acetal
Carboxylic acid derivative
Ether
Oxirane
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

methyl ester (CHEBI:38471 )
azadirachtin (CHEBI:38471 )

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	1.53	ALOGPS
logP	-0.13	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.43	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	215.34 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	166.24 m³·mol⁻¹	ChemAxon
Polarizability	70.66 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

C00042263

Chemspider ID

21865381

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16126804

PDB ID

Not Available

ChEBI ID

38471

Good Scents ID

Not Available

References

General References

Thoeming G, Draeger G, Poehling HM: Soil application of azadirachtin and 3-tigloyl-azadirachtol to control western flower thrips, Frankliniella occidentalis (Thysanoptera: Thripidae): translocation and persistence in bean plants. Pest Manag Sci. 2006 Aug;62(8):759-67. doi: 10.1002/ps.1239. [PubMed:16752388 ]
Kanokmedhakul S, Kanokmedhakul K, Prajuabsuk T, Panichajakul S, Panyamee P, Prabpai S, Kongsaeree P: Azadirachtin derivatives from seed kernels of Azadirachta excelsa. J Nat Prod. 2005 Jul;68(7):1047-50. doi: 10.1021/np050064t. [PubMed:16038546 ]
Sengupta P, Raman S, Chowdhury R, Lohitesh K, Saini H, Mukherjee S, Paul A: Evaluation of Apoptosis and Autophagy Inducing Potential of Berberis aristata, Azadirachta indica, and Their Synergistic Combinations in Parental and Resistant Human Osteosarcoma Cells. Front Oncol. 2017 Dec 11;7:296. doi: 10.3389/fonc.2017.00296. eCollection 2017. [PubMed:29312880 ]
Kushwaha P, Khedgikar V, Haldar S, Gautam J, Mulani FA, Thulasiram HV, Trivedi R: Azadirachta indica triterpenoids promote osteoblast differentiation and mineralization in vitro and in vivo. Bioorg Med Chem Lett. 2016 Aug 1;26(15):3719-24. doi: 10.1016/j.bmcl.2016.05.076. Epub 2016 May 27. [PubMed:27317644 ]
Akihisa T, Noto T, Takahashi A, Fujita Y, Banno N, Tokuda H, Koike K, Suzuki T, Yasukawa K, Kimura Y: Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects of limonoids from the seeds of Azadirachta indicia A. Juss. (neem). J Oleo Sci. 2009;58(11):581-94. doi: 10.5650/jos.58.581. [PubMed:19844073 ]
Silva JC, Jham GN, Oliveira RD, Brown L: Purification of the seven tetranortriterpenoids in neem (Azadirachta indica) seed by counter-current chromatography sequentially followed by isocratic preparative reversed-phase high-performance liquid chromatography. J Chromatogr A. 2007 Jun 1;1151(1-2):203-10. doi: 10.1016/j.chroma.2007.03.086. Epub 2007 Mar 30. [PubMed:17428489 ]
Caboni P, Sarais G, Angioni A, Garcia AJ, Lai F, Dedola F, Cabras P: Residues and persistence of neem formulations on strawberry after field treatment. J Agric Food Chem. 2006 Dec 27;54(26):10026-32. doi: 10.1021/jf062461v. [PubMed:17177537 ]
Thompson DG, Chartrand DT, Kreutzweiser DP: Fate and effects of azadirachtin in aquatic mesocosms--1: fate in water and bottom sediments. Ecotoxicol Environ Saf. 2004 Oct;59(2):186-93. doi: 10.1016/j.ecoenv.2003.09.007. [PubMed:15327874 ]
Sharma V, Walia S, Kumar J, Nair MG, Parmar BS: An efficient method for the purification and characterization of nematicidal azadirachtins A, B, and H, using MPLC and ESIMS. J Agric Food Chem. 2003 Jul 2;51(14):3966-72. doi: 10.1021/jf0342167. [PubMed:12822931 ]

Showing NP-Card for Azadirachtin B (NP0078323)

MOL for NP0078323 (Azadirachtin B)

3D MOL for NP0078323 (Azadirachtin B)

3D SDF for NP0078323 (Azadirachtin B)

3D-SDF for NP0078323 (Azadirachtin B)

PDB for NP0078323 (Azadirachtin B)

3D PDB for NP0078323 (Azadirachtin B)

SMILES for NP0078323 (Azadirachtin B)

INCHI for NP0078323 (Azadirachtin B)

Structure for NP0078323 (Azadirachtin B)

3D Structure for NP0078323 (Azadirachtin B)