NP-MRD: Showing NP-Card for azadirachtin i (NP0205387)

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Record Information

Version

2.0

Created at

2022-09-05 01:17:14 UTC

Updated at

2022-09-05 01:17:14 UTC

NP-MRD ID

NP0205387

Secondary Accession Numbers

None

Natural Product Identification

Common Name

azadirachtin i

Description

Azadirachtin I 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 i is found in Azadirachta indica. azadirachtin i was first documented in 2004 (PMID: 14685815). Based on a literature review a small amount of articles have been published on azadirachtin I (PMID: 26765324) (PMID: 25919947) (PMID: 25919858).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052203172D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052203172D          

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    1.5999   -4.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6263   -1.4399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0577   -2.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7372   -0.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8310   -0.1751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6395   -0.0111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0586    0.6996    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6527    1.4178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836    0.6919    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6614    0.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7478    1.5057    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9465    1.3095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1772    2.1016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3702    2.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2874    2.9192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0958    2.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5694    1.5803    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0234    2.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7679    3.0535    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2818    3.6989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8268    4.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0317    4.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9953    3.3429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2868    3.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2894   -0.0263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0948   -0.2053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7130    0.3411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1734   -1.0265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -1.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8703   -0.7369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0454   -0.7293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  1  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 30 29  1  1  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 32 36  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  6  0  0  0
 22 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  6  0  0  0
  8 43  1  0  0  0  0
 38 43  1  0  0  0  0
 44 43  1  6  0  0  0
 19 44  1  0  0  0  0
 15 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0205387

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)O[C@H]1C[C@@H](OC(C)=O)[C@@]2(C)CO[C@@H]3[C@@H]2[C@]11CO[C@H](O)[C@H]1[C@@](C)([C@@H]3O)[C@]12O[C@@]1(C)[C@H]1C[C@@H]2O[C@@H]2OC=C[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C32H42O12/c1-7-14(2)24(35)42-18-11-17(41-15(3)33)27(4)12-39-20-21(27)30(18)13-40-25(36)22(30)28(5,23(20)34)32-19-10-16(29(32,6)44-32)31(37)8-9-38-26(31)43-19/h7-9,16-23,25-26,34,36-37H,10-13H2,1-6H3/b14-7+/t16-,17-,18+,19+,20-,21+,22+,23-,25+,26+,27-,28+,29+,30+,31+,32+/m1/s1

> <INCHI_KEY>
DTVGLMFEPSBEIA-GSWRAVRCSA-N

> <FORMULA>
C32H42O12

> <MOLECULAR_WEIGHT>
618.676

> <EXACT_MASS>
618.267626792

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
62.24980005549493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,5R,6S,7S,8R,11R,12R,14S,15S)-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]-6,11-dimethyl-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecan-14-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
0.3676896896666682

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.494619964057588

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.895294340949295

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3950931949364183

> <JCHEM_POLAR_SURFACE_AREA>
162.73999999999998

> <JCHEM_REFRACTIVITY>
148.64110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,6S,7S,8R,11R,12R,14S,15S)-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]-6,11-dimethyl-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecan-14-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      12.251  -5.441   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.711  -5.426   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.953  -4.086   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.735  -2.759   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.413  -4.071   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.631  -5.398   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.656  -2.731   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.960  -2.869   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.333  -4.043   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.793  -4.029   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.011  -5.355   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.769  -6.696   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.309  -6.710   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.986  -8.022   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.036  -2.688   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.974  -3.804   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.376  -1.857   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.551  -0.327   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.060  -0.021   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.843   1.306   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.085   2.647   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.383   1.292   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.835   1.805   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.129   2.811   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.633   2.444   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.064   3.923   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.558   4.242   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.270   5.449   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.779   4.499   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.663   2.950   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.510   4.236   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.033   5.700   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.993   6.905   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.143   8.189   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.659   7.779   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.591   6.240   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.269   7.029   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.140  -0.049   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.644  -0.383   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       8.798   0.637   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       7.790  -1.916   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.378  -2.530   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.358  -1.376   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.818  -1.361   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   43                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   17   44                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   44                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   38                                             
CONECT   23   22                                                            
CONECT   24   22   25   26   30                                             
CONECT   25   24   26                                                       
CONECT   26   25   24   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   24   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   32   28   37                                             
CONECT   37   36                                                            
CONECT   38   22   39   43                                                  
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42    8   38   44                                             
CONECT   44   43   19   15                                                  
MASTER        0    0    0    0    0    0    0    0   44    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₂O₁₂

Average Mass

618.6760 Da

Monoisotopic Mass

618.26763 Da

IUPAC Name

(1S,4S,5R,6S,7S,8R,11R,12R,14S,15S)-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]-6,11-dimethyl-3,9-dioxatetracyclo[6.6.1.0^{1,5}.0^{11,15}]pentadecan-14-yl (2E)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)O[C@H]1C[C@@H](OC(C)=O)[C@@]2(C)CO[C@@H]3[C@@H]2[C@]11CO[C@H](O)[C@H]1[C@@](C)([C@@H]3O)[C@]12O[C@@]1(C)[C@H]1C[C@@H]2O[C@@H]2OC=C[C@]12O

InChI Identifier

InChI=1S/C32H42O12/c1-7-14(2)24(35)42-18-11-17(41-15(3)33)27(4)12-39-20-21(27)30(18)13-40-25(36)22(30)28(5,23(20)34)32-19-10-16(29(32,6)44-32)31(37)8-9-38-26(31)43-19/h7-9,16-23,25-26,34,36-37H,10-13H2,1-6H3/b14-7+/t16-,17-,18+,19+,20-,21+,22+,23-,25+,26+,27-,28+,29+,30+,31+,32+/m1/s1

InChI Key

DTVGLMFEPSBEIA-GSWRAVRCSA-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
Furopyran
Fatty acid ester
Oxepane
Dicarboxylic acid or derivatives
Oxane
Pyran
Fatty acyl
Tetrahydrofuran
Tertiary alcohol
Dihydrofuran
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Furan
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Ether
Oxirane
Organoheterocyclic compound
Acetal
Dialkyl ether
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

azadirachtin (CHEBI:38520 )

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	0.37	ChemAxon
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	162.74 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	148.64 m³·mol⁻¹	ChemAxon
Polarizability	62.25 Å³	ChemAxon
Number of Rings	8	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

21865383

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16722130

PDB ID

Not Available

ChEBI ID

38520

Good Scents ID

Not Available

References

General References

Shi H, Tan C, Zhang W, Zhang Z, Long R, Gong J, Luo T, Yang Z: Gold-Catalyzed Enantio- and Diastereoselective Syntheses of Left Fragments of Azadirachtin/Meliacarpin-Type Limonoids. J Org Chem. 2016 Feb 5;81(3):751-71. doi: 10.1021/acs.joc.5b02560. Epub 2016 Jan 25. [PubMed:26765324 ]
Tan C, Chen W, Mu X, Chen Q, Gong J, Luo T, Yang Z: Synthetic Progress toward Azadirachtins. 2. Enantio- and Diastereoselective Synthesis of the Right-Wing Fragment of 11-epi-Azadirachtin I. Org Lett. 2015 May 15;17(10):2338-41. doi: 10.1021/acs.orglett.5b00831. Epub 2015 Apr 28. [PubMed:25919947 ]
Shi H, Tan C, Zhang W, Zhang Z, Long R, Luo T, Yang Z: Synthetic Progress toward Azadirachtins. 1. Enantio- and Diastereoselective Synthesis of the Left-Wing Fragment of 11-epi-Azadirachtin I. Org Lett. 2015 May 15;17(10):2342-5. doi: 10.1021/acs.orglett.5b00829. Epub 2015 Apr 28. [PubMed:25919858 ]
Barrek S, Paisse O, Grenier-Loustalot MF: Analysis of neem oils by LC-MS and degradation kinetics of azadirachtin-A in a controlled environment. Characterization of degradation products by HPLC-MS-MS. Anal Bioanal Chem. 2004 Feb;378(3):753-63. doi: 10.1007/s00216-003-2377-0. Epub 2003 Dec 18. [PubMed:14685815 ]
LOTUS database [Link]

Showing NP-Card for azadirachtin i (NP0205387)

MOL for NP0205387 (azadirachtin i)

3D MOL for NP0205387 (azadirachtin i)

3D SDF for NP0205387 (azadirachtin i)

3D-SDF for NP0205387 (azadirachtin i)

PDB for NP0205387 (azadirachtin i)

3D PDB for NP0205387 (azadirachtin i)

SMILES for NP0205387 (azadirachtin i)

INCHI for NP0205387 (azadirachtin i)

Structure for NP0205387 (azadirachtin i)

3D Structure for NP0205387 (azadirachtin i)