NP-MRD: Showing NP-Card for 13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate (NP0286862)

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Record Information

Version

2.0

Created at

2022-09-09 15:39:18 UTC

Updated at

2022-09-09 15:39:18 UTC

NP-MRD ID

NP0286862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate

Description

13-(Acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-9-en-14-yl 2-methylpropanoate 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. 13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate is found in Carapa guianensis. 13-(Acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-9-en-14-yl 2-methylpropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261502062D          

 43 47  0  0  0  0            999 V2000
    0.6976   -2.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5382   -1.7646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8638   -2.0407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -0.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2194   -0.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587   -0.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -0.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1974   -0.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0207   -0.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3871   -0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8441   -0.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104   -0.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767    0.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1197    1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4860    2.0741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2963    1.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300    0.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663    1.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8430    1.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    1.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9554    3.6487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3804   -1.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 37 38  2  0  0  0  0
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 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 39 43  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004261502062D          

 43 47  0  0  0  0            999 V2000
    0.6976   -2.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5382   -1.7646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3871   -0.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8441   -0.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2104   -0.0912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5767    0.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1197    1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4860    2.0741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2963    1.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300    0.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1067    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663    1.1760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8430    1.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1038    1.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1593    2.4620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999    2.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554    3.6487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850    2.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220    1.3752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2207    1.9965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0459    2.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8554    2.9366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4968    3.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3063    3.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2301    4.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0443    0.6360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7579    1.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    0.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7623    0.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291    1.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6674   -0.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -0.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7141   -1.6064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0273   -2.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3804   -1.5515    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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 27 34  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 22 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  2  0  0  0  0
 13 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 39 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286862

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1C2C3CCC4(C)C(OC(=O)C=C4C3(O)CC(OC(C)=O)(C(OC(=O)C(C)C)C1(C)C)C2=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O11/c1-16(2)27(37)42-28-29(4,5)20(12-22(34)39-7)24-19-8-10-30(6)21(13-23(35)41-26(30)18-9-11-40-14-18)31(19,38)15-32(28,25(24)36)43-17(3)33/h9,11,13-14,16,19-20,24,26,28,38H,8,10,12,15H2,1-7H3

> <INCHI_KEY>
NBVHJDYRVKSYBM-UHFFFAOYSA-N

> <FORMULA>
C32H40O11

> <MOLECULAR_WEIGHT>
600.661

> <EXACT_MASS>
600.257062108

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
62.05722551687872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate

> <ALOGPS_LOGP>
3.13

> <JCHEM_LOGP>
3.3421665340000013

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.171016765937516

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.769198487688694

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8887989111967802

> <JCHEM_POLAR_SURFACE_AREA>
155.64

> <JCHEM_REFRACTIVITY>
148.71749999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       1.302  -4.805   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.005  -3.294   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.453  -2.796   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.612  -3.809   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.750  -1.285   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.410  -0.272   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.789  -0.956   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.249  -0.464   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.102  -1.746   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.639  -1.648   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.322  -0.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.176  -1.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.859  -0.170   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.543   1.210   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.690   2.492   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.374   3.872   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.153   2.394   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.469   1.014   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.932   0.916   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.790   2.195   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.440   2.376   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.060   3.059   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.164   4.596   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.546   5.274   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.650   6.811   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.825   4.416   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.601   2.567   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.412   3.727   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.086   5.184   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.597   5.482   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.927   6.344   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.438   6.046   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.430   7.801   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.083   1.187   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.415   1.960   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.507   0.601   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.423   1.086   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.241   2.073   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       8.713  -1.452   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.251  -1.516   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      10.666  -2.999   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       9.384  -3.852   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.177  -2.896   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   34                                                  
CONECT    7    6    8   37                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   18                                             
CONECT   12   11                                                            
CONECT   13   11   14   39                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18    8   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   27   37                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   27    6   35   36                                             
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   22    7   38                                                  
CONECT   38   37                                                            
CONECT   39   13   40   43                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   39                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
13-(Acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0,.0,]heptadec-9-en-14-yl 2-methylpropanoic acid	Generator
13-(Acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₃₂H₄₀O₁₁

Average Mass

600.6610 Da

Monoisotopic Mass

600.25706 Da

IUPAC Name

13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate

Traditional Name

13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

COC(=O)CC1C2C3CCC4(C)C(OC(=O)C=C4C3(O)CC(OC(C)=O)(C(OC(=O)C(C)C)C1(C)C)C2=O)C1=COC=C1

InChI Identifier

InChI=1S/C32H40O11/c1-16(2)27(37)42-28-29(4,5)20(12-22(34)39-7)24-19-8-10-30(6)21(13-23(35)41-26(30)18-9-11-40-14-18)31(19,38)15-32(28,25(24)36)43-17(3)33/h9,11,13-14,16,19-20,24,26,28,38H,8,10,12,15H2,1-7H3

InChI Key

NBVHJDYRVKSYBM-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
Carapa guianensis	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
Mexicanolide
Naphthopyran
Tetracarboxylic acid or derivatives
Naphthalene
Dihydropyranone
Alpha-acyloxy ketone
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.13	ALOGPS
logP	3.34	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.77	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	155.64 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	148.72 m³·mol⁻¹	ChemAxon
Polarizability	62.06 Å³	ChemAxon
Number of Rings	5	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate (NP0286862)

MOL for NP0286862 (13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate)

3D MOL for NP0286862 (13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate)

3D SDF for NP0286862 (13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate)

3D-SDF for NP0286862 (13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate)

PDB for NP0286862 (13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate)

3D PDB for NP0286862 (13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate)

SMILES for NP0286862 (13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate)

INCHI for NP0286862 (13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate)

Structure for NP0286862 (13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate)

3D Structure for NP0286862 (13-(acetyloxy)-6-(furan-3-yl)-11-hydroxy-16-(2-methoxy-2-oxoethyl)-5,15,15-trimethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]heptadec-9-en-14-yl 2-methylpropanoate)