NP-MRD: Showing NP-Card for azadirachtin h (NP0156552)

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Record Information

Version

2.0

Created at

2022-09-02 13:46:35 UTC

Updated at

2022-09-02 13:46:35 UTC

NP-MRD ID

NP0156552

Secondary Accession Numbers

None

Natural Product Identification

Common Name

azadirachtin h

Description

Azadirachtin H 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 h is found in Azadirachta indica. azadirachtin h was first documented in 2003 (PMID: 12822931). Based on a literature review a small amount of articles have been published on azadirachtin H (PMID: 35480004) (PMID: 16038546) (PMID: 17428489).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022215462D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022215462D          

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    4.1012   -1.4628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1930   -1.5369    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8571   -2.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0322   -2.1582    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6131   -2.8688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0190   -3.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8439   -3.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    1.2912   -2.8290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2557   -1.8443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0223   -1.0530    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
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 33 32  1  1  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 35 39  1  0  0  0  0
 31 39  1  0  0  0  0
 39 40  1  6  0  0  0
 25 41  1  0  0  0  0
 41 42  1  6  0  0  0
 42 43  1  1  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 46 45  1  6  0  0  0
  8 46  1  0  0  0  0
 41 46  1  0  0  0  0
 47 46  1  6  0  0  0
 22 47  1  0  0  0  0
 15 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0156552

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]12CO[C@@H]3[C@@H]1[C@]1(CO[C@H](O)[C@H]1[C@@](C)([C@@H]3O)[C@]13O[C@@]1(C)[C@H]1C[C@@H]3O[C@@H]3OC=C[C@]13O)[C@H](C[C@H]2OC(C)=O)OC(=O)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O14/c1-7-14(2)24(36)45-17-11-18(44-15(3)34)31(26(38)40-6)13-42-20-21(31)30(17)12-43-25(37)22(30)28(4,23(20)35)33-19-10-16(29(33,5)47-33)32(39)8-9-41-27(32)46-19/h7-9,16-23,25,27,35,37,39H,10-13H2,1-6H3/b14-7+/t16-,17+,18-,19+,20-,21-,22+,23-,25+,27+,28+,29+,30+,31+,32+,33+/m1/s1

> <INCHI_KEY>
ILMJTWSQVCYIKY-YAYGENDCSA-N

> <FORMULA>
C33H42O14

> <MOLECULAR_WEIGHT>
662.685

> <EXACT_MASS>
662.257456032

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
65.57550144240605

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,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-11-carboxylate

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
-0.2947236553333338

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.494564003896155

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.895265774201953

> <JCHEM_PKA_STRONGEST_BASIC>
-3.395494254608005

> <JCHEM_POLAR_SURFACE_AREA>
189.03999999999996

> <JCHEM_REFRACTIVITY>
155.12740000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,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-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      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  O   UNK     0       2.410  -5.281   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.477  -3.443   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.042  -1.966   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.376  -1.857   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.551  -0.327   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.060  -0.021   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.843   1.306   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.085   2.647   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.383   1.292   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.835   1.805   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.129   2.811   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.633   2.444   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.064   3.923   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.558   4.242   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.270   5.449   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.779   4.499   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.663   2.950   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.510   4.236   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.033   5.700   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.993   6.905   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.143   8.189   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.659   7.779   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.591   6.240   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.269   7.029   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.140  -0.049   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.644  -0.383   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       8.798   0.637   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       7.790  -1.916   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       6.378  -2.530   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.358  -1.376   0.000  0.00  0.00           C+0
HETATM   47  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   46                                                  
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   20   47                                             
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   47                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   41                                             
CONECT   26   25                                                            
CONECT   27   25   28   29   33                                             
CONECT   28   27   29                                                       
CONECT   29   28   27   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32   39                                                  
CONECT   32   31   33                                                       
CONECT   33   32   27   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   39                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   35   31   40                                             
CONECT   40   39                                                            
CONECT   41   25   42   46                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45    8   41   47                                             
CONECT   47   46   22   15                                                  
MASTER        0    0    0    0    0    0    0    0   47    0  108    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₂O₁₄

Average Mass

662.6850 Da

Monoisotopic Mass

662.25746 Da

IUPAC Name

methyl (1S,4S,5R,6S,7S,8R,11S,12R,14S,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-11-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]12CO[C@@H]3[C@@H]1[C@]1(CO[C@H](O)[C@H]1[C@@](C)([C@@H]3O)[C@]13O[C@@]1(C)[C@H]1C[C@@H]3O[C@@H]3OC=C[C@]13O)[C@H](C[C@H]2OC(C)=O)OC(=O)C(\C)=C\C

InChI Identifier

InChI=1S/C33H42O14/c1-7-14(2)24(36)45-17-11-18(44-15(3)34)31(26(38)40-6)13-42-20-21(31)30(17)12-43-25(37)22(30)28(4,23(20)35)33-19-10-16(29(33,5)47-33)32(39)8-9-41-27(32)46-19/h7-9,16-23,25,27,35,37,39H,10-13H2,1-6H3/b14-7+/t16-,17+,18-,19+,20-,21-,22+,23-,25+,27+,28+,29+,30+,31+,32+,33+/m1/s1

InChI Key

ILMJTWSQVCYIKY-YAYGENDCSA-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
Tricarboxylic acid or derivatives
Fatty acid ester
Oxepane
Oxane
Fatty acyl
Pyran
Cyclic alcohol
Dihydrofuran
Furan
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Tetrahydrofuran
Enoate ester
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:38510 )
azadirachtin (CHEBI:38510 )

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	1.19	ALOGPS
logP	-0.29	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.9	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	189.04 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	155.13 m³·mol⁻¹	ChemAxon
Polarizability	65.58 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

C00042041

Chemspider ID

21865382

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16722121

PDB ID

Not Available

ChEBI ID

38510

Good Scents ID

Not Available

References

General References

Shadrack DM, Vuai SAH, Sahini MG, Onoka I: In silico study of the inhibition of SARS-COV-2 viral cell entry by neem tree extracts. RSC Adv. 2021 Aug 3;11(43):26524-26533. doi: 10.1039/d1ra04197e. eCollection 2021 Aug 2. [PubMed:35480004 ]
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 ]
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 ]
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 ]
LOTUS database [Link]

Showing NP-Card for azadirachtin h (NP0156552)

MOL for NP0156552 (azadirachtin h)

3D MOL for NP0156552 (azadirachtin h)

3D SDF for NP0156552 (azadirachtin h)

3D-SDF for NP0156552 (azadirachtin h)

PDB for NP0156552 (azadirachtin h)

3D PDB for NP0156552 (azadirachtin h)

SMILES for NP0156552 (azadirachtin h)

INCHI for NP0156552 (azadirachtin h)

Structure for NP0156552 (azadirachtin h)

3D Structure for NP0156552 (azadirachtin h)