NP-MRD: Showing NP-Card for Azadirachtin A (NP0052185)

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Record Information

Version

1.0

Created at

2022-04-27 23:20:05 UTC

Updated at

2022-04-27 23:20:05 UTC

NP-MRD ID

NP0052185

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Azadirachtin A

Description

Azadirachtin A, also known as bioneem or neemix, 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. Thus, azadirachtin a is considered to be an isoprenoid lipid molecule. Azadirachtin A is found in Azadirachta indica and Turraea pubescens. It was first documented in 2002 (PMID: 11990361). Azadirachtin A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 24708208).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307282022142D          

 61 68  0  0  1  0            999 V2000
   -0.9522    2.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 23  1  0  0  0  0
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M  END

     RDKit          3D

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 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 51  1  0
 51 50  1  0
 50 49  1  6
 49 48  1  0
 48 42  1  0
 42 43  1  6
 42 44  1  0
 44 45  2  0
 44 46  1  0
 46 47  1  0
 42 41  1  0
 41 25  1  0
 25 26  1  6
 25 23  1  0
 23 24  1  0
 25 27  1  0
 27 28  1  6
 28 29  1  0
 29 30  1  1
 29 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  1
 15 16  1  6
 16 17  2  0
 16 18  1  0
 18 19  1  0
 50  8  1  0
 41 50  1  0
 29 27  1  0
 39 31  1  0
 51 15  1  0
 33 27  1  0
 39 35  1  0
 23 22  1  0
  2 55  1  0
  1 52  1  0
  1 53  1  0
  1 54  1  0
  4 56  1  0
  4 57  1  0
  4 58  1  0
  8 59  1  6
  9 60  1  0
  9 61  1  0
 10 62  1  6
 13 63  1  0
 13 64  1  0
 13 65  1  0
 20 69  1  0
 20 70  1  0
 22 71  1  6
 51 95  1  1
 49 93  1  0
 49 94  1  0
 43 89  1  0
 47 90  1  0
 47 91  1  0
 47 92  1  0
 41 88  1  1
 26 74  1  0
 26 75  1  0
 26 76  1  0
 23 72  1  1
 24 73  1  0
 30 77  1  0
 30 78  1  0
 30 79  1  0
 31 80  1  1
 32 81  1  0
 32 82  1  0
 33 83  1  6
 35 84  1  1
 37 85  1  0
 38 86  1  0
 40 87  1  0
 19 66  1  0
 19 67  1  0
 19 68  1  0
M  END


  Mrv1652307282022142D          

 61 68  0  0  1  0            999 V2000
   -0.9522    2.6872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1442    1.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0144    4.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9391   -1.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2268   -2.5136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5834    0.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5621   -0.7185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1273    2.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -4.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7646   -4.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5008   -2.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7515    1.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8684    0.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0768    1.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2767    1.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5935    3.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3079   -3.1578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3306    1.2192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5765    1.9189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0294   -1.8155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9635   -0.2293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5595    0.4900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5425   -0.9388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1017    1.9483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136   -0.2097    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5506    1.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6838   -0.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8270   -3.2883    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7176   -0.9290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4202   -2.3405    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7346    0.4998    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9805    1.1996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5989   -3.5796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5087   -0.0286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8512   -1.7431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7685    3.3575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9465   -1.6581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5226    2.6578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3192    2.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2798    0.7005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3063   -4.0041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4128   -0.8480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3521    1.6003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2628   -0.7283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3114   -3.9323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7725   -0.0674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4323    0.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9974    2.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5056    1.2290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5736   -2.5032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6531   -1.5491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2937    3.3869    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1309   -3.2149    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9266    1.9385    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4014    1.9091    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2242   -1.6358    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1386   -0.2195    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1555    1.2094    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3675   -0.9486    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8208   -0.8713    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0156   -3.1394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
 10  9  2  0  0  0  0
 15  2  1  0  0  0  0
 15  8  2  0  0  0  0
 16  3  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 12  1  0  0  0  0
 20 11  1  0  0  0  0
 22 21  1  0  0  0  0
 23 21  1  0  0  0  0
 24 15  1  0  0  0  0
 29  4  1  6  0  0  0
 29 23  1  0  0  0  0
 29 25  1  0  0  0  0
 30  5  1  6  0  0  0
 30 17  1  0  0  0  0
 31 14  1  6  0  0  0
 31 18  1  0  0  0  0
 31 22  1  0  0  0  0
 31 25  1  0  0  0  0
 32 13  1  0  0  0  0
 32 19  1  0  0  0  0
 32 22  1  0  0  0  0
 32 26  1  6  0  0  0
 33  9  1  0  0  0  0
 33 17  1  0  0  0  0
 33 28  1  0  0  0  0
 34 25  1  0  0  0  0
 34 27  1  1  0  0  0
 35 20  1  0  0  0  0
 29 35  1  1  0  0  0
 35 30  1  0  0  0  0
 36 16  2  0  0  0  0
 23 37  1  1  0  0  0
 38 24  2  0  0  0  0
 39 26  2  0  0  0  0
 40 27  2  0  0  0  0
 33 41  1  6  0  0  0
 34 42  1  6  0  0  0
 43  6  1  0  0  0  0
 43 26  1  0  0  0  0
 44  7  1  0  0  0  0
 44 27  1  0  0  0  0
 45 10  1  0  0  0  0
 45 28  1  0  0  0  0
 46 13  1  0  0  0  0
 46 21  1  0  0  0  0
 47 14  1  0  0  0  0
 47 34  1  0  0  0  0
 48 16  1  0  0  0  0
 19 48  1  1  0  0  0
 18 49  1  1  0  0  0
 49 24  1  0  0  0  0
 50 20  1  0  0  0  0
 50 28  1  0  0  0  0
 51 30  1  0  0  0  0
 35 51  1  1  0  0  0
 52  8  1  0  0  0  0
 17 53  1  1  0  0  0
 18 54  1  6  0  0  0
 19 55  1  6  0  0  0
 20 56  1  1  0  0  0
 21 57  1  6  0  0  0
 22 58  1  1  0  0  0
 23 59  1  6  0  0  0
 25 60  1  1  0  0  0
 28 61  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052185

> <DATABASE_NAME>
NP-MRD

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

> <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-NDAWSKJSSA-N

> <FORMULA>
C35H44O16

> <MOLECULAR_WEIGHT>
720.721

> <EXACT_MASS>
720.262935337

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
70.3540331781818

> <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,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-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>
215.33999999999992

> <JCHEM_REFRACTIVITY>
166.23890000000006

> <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,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-4,11-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-20         0                                  
HETATM    1  C   UNK     0      -1.777   5.016   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.269   2.331   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   7.573   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.620  -2.244   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.890  -4.692   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.422   1.509   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.049  -1.341   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.238   4.998   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.779  -8.220   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.294  -8.627   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.668  -4.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.136   3.600   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.088   1.404   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.877   2.036   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.517   3.655   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.708   6.249   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.175  -5.895   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.350   2.276   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.676   3.582   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.788  -3.389   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.399  -0.428   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.644   0.915   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.613  -1.752   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.057   3.637   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.319  -0.391   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.494   3.352   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.276  -0.035   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.410  -6.138   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.073  -1.734   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.384  -4.369   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.105   0.933   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.430   2.239   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.851  -6.682   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.816  -0.053   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.322  -3.254   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.168   6.267   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       7.367  -3.095   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.842   4.961   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       8.063   4.831   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.522   1.308   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       6.172  -7.474   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       2.637  -1.583   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       9.991   2.987   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.491  -1.359   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       2.448  -7.340   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       8.909  -0.126   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       2.674   1.480   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       7.462   4.906   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       2.810   2.294   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       2.937  -4.673   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       6.819  -2.892   0.000  0.00  0.00           O+0
HETATM   52  H   UNK     0       0.548   6.322   0.000  0.00  0.00           H+0
HETATM   53  H   UNK     0       7.711  -6.001   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.596   3.619   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       8.216   3.564   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.285  -3.053   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.859  -0.410   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0       5.890   2.258   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       8.153  -1.771   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.399  -1.626   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.896  -5.860   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   29                                                            
CONECT    5   30                                                            
CONECT    6   43                                                            
CONECT    7   44                                                            
CONECT    8    1   15   52                                                  
CONECT    9   10   33                                                       
CONECT   10    9   45                                                       
CONECT   11   17   20                                                       
CONECT   12   18   19                                                       
CONECT   13   32   46                                                       
CONECT   14   31   47                                                       
CONECT   15    2    8   24                                                  
CONECT   16    3   36   48                                                  
CONECT   17   11   30   33   53                                             
CONECT   18   12   31   49   54                                             
CONECT   19   12   32   48   55                                             
CONECT   20   11   35   50   56                                             
CONECT   21   22   23   46   57                                             
CONECT   22   21   31   32   58                                             
CONECT   23   21   29   37   59                                             
CONECT   24   15   38   49                                                  
CONECT   25   29   31   34   60                                             
CONECT   26   32   39   43                                                  
CONECT   27   34   40   44                                                  
CONECT   28   33   45   50   61                                             
CONECT   29    4   23   25   35                                             
CONECT   30    5   17   35   51                                             
CONECT   31   14   18   22   25                                             
CONECT   32   13   19   22   26                                             
CONECT   33    9   17   28   41                                             
CONECT   34   25   27   42   47                                             
CONECT   35   20   29   30   51                                             
CONECT   36   16                                                            
CONECT   37   23                                                            
CONECT   38   24                                                            
CONECT   39   26                                                            
CONECT   40   27                                                            
CONECT   41   33                                                            
CONECT   42   34                                                            
CONECT   43    6   26                                                       
CONECT   44    7   27                                                       
CONECT   45   10   28                                                       
CONECT   46   13   21                                                       
CONECT   47   14   34                                                       
CONECT   48   16   19                                                       
CONECT   49   18   24                                                       
CONECT   50   20   28                                                       
CONECT   51   30   35                                                       
CONECT   52    8                                                            
CONECT   53   17                                                            
CONECT   54   18                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   21                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   25                                                            
CONECT   61   28                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  136    0
END

View in JSmol

Synonyms

Value	Source
Azadirachtin	ChEBI
Azadyrachtin	MeSH
Bioneem	MeSH
Neemix	MeSH

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,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-4,11-dicarboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

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

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-NDAWSKJSSA-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
Turraea pubescens	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
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

tertiary alcohol (CHEBI:2942 )
organic heterotetracyclic compound (CHEBI:2942 )
secondary alcohol (CHEBI:2942 )
epoxide (CHEBI:2942 )
acetate ester (CHEBI:2942 )
methyl ester (CHEBI:2942 )
cyclic hemiketal (CHEBI:2942 )
enoate ester (CHEBI:2942 )
azadirachtin (CHEBI:2942 )
Apotirucallane triterpenoids (C08748 )
Apotirucallane triterpenoids (LMPR0106100001 )

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	70.35 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

C00003698

Chemspider ID

Not Available

KEGG Compound ID

C08748

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Azadirachtin

METLIN ID

Not Available

PubChem Compound

5281303

PDB ID

Not Available

ChEBI ID

2942

Good Scents ID

Not Available

References

General References

Johnson S, Dureja P: Effect of surfactants on persistence of azadirachtin-A (neem based pesticide). J Environ Sci Health B. 2002 Jan;37(1):75-80. doi: 10.1081/PFC-120002899. [PubMed:11990361 ]
Baligar NS, Aladakatti RH, Ahmed M, Hiremath MB: Hepatoprotective activity of the neem-based constituent azadirachtin-A in carbon tetrachloride intoxicated Wistar rats. Can J Physiol Pharmacol. 2014 Apr;92(4):267-77. doi: 10.1139/cjpp-2013-0449. Epub 2014 Jan 9. [PubMed:24708208 ]

Showing NP-Card for Azadirachtin A (NP0052185)

MOL for NP0052185 (Azadirachtin A)

3D MOL for NP0052185 (Azadirachtin A)

3D SDF for NP0052185 (Azadirachtin A)

3D-SDF for NP0052185 (Azadirachtin A)

PDB for NP0052185 (Azadirachtin A)

3D PDB for NP0052185 (Azadirachtin A)

SMILES for NP0052185 (Azadirachtin A)

INCHI for NP0052185 (Azadirachtin A)

Structure for NP0052185 (Azadirachtin A)

3D Structure for NP0052185 (Azadirachtin A)