NP-MRD: Showing NP-Card for 14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate (NP0215857)

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Record Information

Version

2.0

Created at

2022-09-05 15:36:59 UTC

Updated at

2022-09-05 15:36:59 UTC

NP-MRD ID

NP0215857

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate

Description

14-Hydroxy-6-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]Octadec-7-en-12-yl 3-methylbut-2-enoate 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. 14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate is found in Azadirachta indica. 14-Hydroxy-6-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]Octadec-7-en-12-yl 3-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151514092D          

 42 47  0  0  0  0            999 V2000
    3.7948   -3.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4019   -2.8036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2217   -1.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8288   -1.4399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4343   -1.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541   -0.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4668   -0.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326   -1.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855   -1.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8577    0.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1388    0.4937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676    0.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950    0.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7304    1.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499    1.4131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936    0.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6809    0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3909    0.8369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0099    0.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6085   -3.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 39 40  2  0  0  0  0
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 40 42  1  0  0  0  0
M  END

     RDKit          3D

 84 89  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004151514092D          

 42 47  0  0  0  0            999 V2000
    3.7948   -3.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5855   -1.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8577    0.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1388    0.4937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676    0.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8950    0.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7304    1.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499    1.4131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8936    0.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6809    0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3909    0.8369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0099    0.2915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8313    0.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0115   -0.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3016   -1.0111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825   -0.4658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8612   -0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1246   -1.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242   -1.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7688   -0.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4788   -0.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0978   -1.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9029   -0.8632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7704   -1.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9491   -1.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4037   -2.3424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    0.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650   -1.9654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8405   -2.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365   -1.9300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8200   -3.1848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0956   -3.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0751   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -3.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
  6 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 17 35  1  0  0  0  0
  7 35  1  0  0  0  0
 13 35  1  0  0  0  0
  9 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215857

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1C2(C)C(OC3CC(C(C)=C23)C2=CC(=O)OC2O)C2OCC3(C)C2C1(C)C(CC3O)OC(=O)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H42O10/c1-14(2)8-23(35)41-21-12-20(33)30(4)13-39-26-27(30)31(21,5)19(11-22(34)38-7)32(6)25-15(3)16(9-18(25)40-28(26)32)17-10-24(36)42-29(17)37/h8,10,16,18-21,26-29,33,37H,9,11-13H2,1-7H3

> <INCHI_KEY>
LWHAGFHXOKLHEU-UHFFFAOYSA-N

> <FORMULA>
C32H42O10

> <MOLECULAR_WEIGHT>
586.678

> <EXACT_MASS>
586.277797552

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
62.42255054177674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-hydroxy-6-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.1533668303333333

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.775722058151349

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.755313824436019

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9995708796707863

> <JCHEM_POLAR_SURFACE_AREA>
137.82000000000002

> <JCHEM_REFRACTIVITY>
149.80680000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-6-(2-hydroxy-5-oxo-2H-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       7.084  -6.276   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.217  -5.233   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.880  -3.731   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.014  -2.688   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.411  -3.271   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.074  -1.768   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.605  -1.308   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.728  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.960  -2.129   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.618  -1.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.601   0.166   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.259   0.922   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.926   0.951   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.671   1.842   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.230   2.460   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.760   2.638   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.401   1.238   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.871   0.778   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.196   1.562   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.352   0.544   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.885   0.400   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.222  -1.103   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.896  -1.887   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.741  -0.869   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.208  -0.725   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.699  -2.184   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.752  -3.421   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.635  -1.714   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.960  -0.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.116  -1.948   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      16.619  -1.611   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      14.505  -3.361   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.972  -3.217   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.954  -4.372   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.268   0.195   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.921  -3.669   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.569  -4.405   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.255  -3.603   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.531  -5.945   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.178  -6.682   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.140  -8.221   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.136  -5.879   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                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8    9   35                                             
CONECT    8    7                                                            
CONECT    9    7   10   36                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   35                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   35                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24   27                                                  
CONECT   24   23   20   25                                                  
CONECT   25   24    6   18   26                                             
CONECT   26   25                                                            
CONECT   27   23                                                            
CONECT   28   22   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   28   34                                                  
CONECT   34   33                                                            
CONECT   35   17    7   13                                                  
CONECT   36    9   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
14-Hydroxy-6-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0,.0,.0,]octadec-7-en-12-yl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₂H₄₂O₁₀

Average Mass

586.6780 Da

Monoisotopic Mass

586.27780 Da

IUPAC Name

14-hydroxy-6-(2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate

Traditional Name

14-hydroxy-6-(2-hydroxy-5-oxo-2H-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)CC1C2(C)C(OC3CC(C(C)=C23)C2=CC(=O)OC2O)C2OCC3(C)C2C1(C)C(CC3O)OC(=O)C=C(C)C

InChI Identifier

InChI=1S/C32H42O10/c1-14(2)8-23(35)41-21-12-20(33)30(4)13-39-26-27(30)31(21,5)19(11-22(34)38-7)32(6)25-15(3)16(9-18(25)40-28(26)32)17-10-24(36)42-29(17)37/h8,10,16,18-21,26-29,33,37H,9,11-13H2,1-7H3

InChI Key

LWHAGFHXOKLHEU-UHFFFAOYSA-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
Naphthofuran
Tricarboxylic acid or derivatives
Fatty acid ester
2-furanone
Fatty acyl
Cyclic alcohol
Dihydrofuran
Tetrahydrofuran
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Hemiacetal
Secondary alcohol
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.54	ALOGPS
logP	2.15	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.76	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	137.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	149.81 m³·mol⁻¹	ChemAxon
Polarizability	62.42 Å³	ChemAxon
Number of Rings	6	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101425842

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate (NP0215857)

MOL for NP0215857 (14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate)

3D MOL for NP0215857 (14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate)

3D SDF for NP0215857 (14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate)

3D-SDF for NP0215857 (14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate)

PDB for NP0215857 (14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate)

3D PDB for NP0215857 (14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate)

SMILES for NP0215857 (14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate)

INCHI for NP0215857 (14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate)

Structure for NP0215857 (14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate)

3D Structure for NP0215857 (14-hydroxy-6-(2-hydroxy-5-oxo-2h-furan-3-yl)-10-(2-methoxy-2-oxoethyl)-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadec-7-en-12-yl 3-methylbut-2-enoate)