NP-MRD: Showing NP-Card for [(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate (NP0257997)

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Record Information

Version

2.0

Created at

2022-09-07 23:17:09 UTC

Updated at

2022-09-07 23:17:09 UTC

NP-MRD ID

NP0257997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate

Description

[(1S,2R,3R,4R,5S,6R,10R,11R,12S,13S,14S,15R,17R,18S)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadecan-1-yl]methyl acetate 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. [(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate is found in Chukrasia tabularis. Based on a literature review very few articles have been published on [(1S,2R,3R,4R,5S,6R,10R,11R,12S,13S,14S,15R,17R,18S)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadecan-1-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082201172D          

 53 58  0  0  1  0            999 V2000
   -1.5872   -3.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7879   -2.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4566   -1.1863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2386   -0.8393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  7 13  1  0  0  0  0
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 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
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 18 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
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 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
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 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
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 37 38  1  1  0  0  0
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 52 53  1  1  0  0  0
M  END

     RDKit          3D

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   -2.8336   -3.2697   -3.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818   -4.5992   -3.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1 54  1  0
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 31 80  1  0
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 39 85  1  0
 44 88  1  0
 44 89  1  0
 44 90  1  0
 45 91  1  1
 46 92  1  0
 47 93  1  1
 50 94  1  0
 50 95  1  0
 50 96  1  0
 53 97  1  0
  8 60  1  0
  8 61  1  0
 11 62  1  0
 11 63  1  0
 11 64  1  0
M  END


  Mrv1652309082201172D          

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   -0.7879   -2.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0679    0.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0444    1.4330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9637    0.6960    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2917    1.4530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8001    2.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9805    2.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1280    2.8726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4759    0.0282    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8132    0.7811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2986    0.0892    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6572    0.8322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4799    0.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385    1.6361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441    0.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5855   -0.5319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0497   -1.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8743   -1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1050   -2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4229   -2.4956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7707   -1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7628   -0.5928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2269   -1.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -1.3358    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8684   -2.0179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5814   -1.3968    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2229   -2.1398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6870   -2.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5098   -2.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3284   -3.5648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1173   -0.7148    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7837   -1.4693    0.0000 O   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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 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
 38 42  2  0  0  0  0
 37 43  1  0  0  0  0
 32 43  1  0  0  0  0
 43 44  1  1  0  0  0
 43 45  1  0  0  0  0
 45 46  1  1  0  0  0
 45 47  1  0  0  0  0
 47 48  1  1  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
 47 52  1  0  0  0  0
  7 52  1  0  0  0  0
 30 52  1  0  0  0  0
 52 53  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0257997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1[C@@]2(C)C[C@]3(O)[C@](O)([C@H]2OC(C)=O)[C@@H](OC(C)=O)[C@]2(O)[C@@H]4CC(=O)O[C@@H](C5=COC=C5)[C@]4(C)[C@@H](O)[C@@H](OC(C)=O)[C@]2(O)[C@]13COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H44O18/c1-15(36)49-14-31-20(10-22(40)47-7)29(5)13-32(31,43)34(45,27(29)51-17(3)38)28(52-18(4)39)33(44)21-11-23(41)53-25(19-8-9-48-12-19)30(21,6)24(42)26(35(31,33)46)50-16(2)37/h8-9,12,20-21,24-28,42-46H,10-11,13-14H2,1-7H3/t20-,21+,24-,25-,26+,27-,28-,29+,30-,31+,32+,33+,34-,35-/m0/s1

> <INCHI_KEY>
QUIUAWAJVAZIOJ-ZDAAGFHHSA-N

> <FORMULA>
C35H44O18

> <MOLECULAR_WEIGHT>
752.719

> <EXACT_MASS>
752.252764577

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
72.04444029522634

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,3R,4R,5S,6R,10R,11R,12S,13S,14S,15R,17R,18S)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadecan-1-yl]methyl acetate

> <JCHEM_LOGP>
-3.088266142666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.157027178794158

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.51440898476561

> <JCHEM_PKA_STRONGEST_BASIC>
-2.88879143495099

> <JCHEM_POLAR_SURFACE_AREA>
272.09

> <JCHEM_REFRACTIVITY>
167.0828

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,3R,4R,5S,6R,10R,11R,12S,13S,14S,15R,17R,18S)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0^{2,11}.0^{5,10}.0^{13,17}]octadecan-1-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.963  -5.943   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.471  -5.562   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.055  -4.079   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.132  -2.978   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.437  -3.697   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.852  -2.214   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.312  -1.567   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.736  -3.047   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.667  -4.155   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.091  -5.635   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.585  -6.008   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.021  -6.743   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.656  -0.228   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.189  -0.084   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.127   0.226   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.088  -0.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.601  -1.142   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.395   1.126   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.561   2.334   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.084   2.110   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.652   0.678   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.040   3.317   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.031   1.137   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.949   2.675   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.666   1.299   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.278   2.712   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.360   3.949   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.830   3.773   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.972   5.362   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.622   0.053   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.251   1.458   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.157   0.167   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.827   1.553   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.363   1.667   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.032   3.054   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       9.229   0.394   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.560  -0.993   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.426  -2.266   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.965  -2.313   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.396  -3.792   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      10.123  -4.658   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.905  -3.715   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.024  -1.107   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       7.890  -2.380   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.354  -2.494   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       7.221  -3.767   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       4.819  -2.607   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       4.149  -3.994   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       5.016  -5.267   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.552  -5.154   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       4.346  -6.654   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       3.952  -1.334   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       3.330  -2.743   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8   13   52                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   15   23                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    6   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   13   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   31   32   52                                             
CONECT   31   30                                                            
CONECT   32   30   33   43                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38   43                                                  
CONECT   38   37   39   42                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   38                                                       
CONECT   43   37   32   44   45                                             
CONECT   44   43                                                            
CONECT   45   43   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   52                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   47    7   30   53                                             
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  116    0
END

View in JSmol

Synonyms

Value	Source
[(1S,2R,3R,4R,5S,6R,10R,11R,12S,13S,14S,15R,17R,18S)-3,12,14-Tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0,.0,.0,]octadecan-1-yl]methyl acetic acid	Generator

Chemical Formula

C₃₅H₄₄O₁₈

Average Mass

752.7190 Da

Monoisotopic Mass

752.25276 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1[C@@]2(C)C[C@]3(O)[C@](O)([C@H]2OC(C)=O)[C@@H](OC(C)=O)[C@]2(O)[C@@H]4CC(=O)O[C@@H](C5=COC=C5)[C@]4(C)[C@@H](O)[C@@H](OC(C)=O)[C@]2(O)[C@]13COC(C)=O

InChI Identifier

InChI=1S/C35H44O18/c1-15(36)49-14-31-20(10-22(40)47-7)29(5)13-32(31,43)34(45,27(29)51-17(3)38)28(52-18(4)39)33(44)21-11-23(41)53-25(19-8-9-48-12-19)30(21,6)24(42)26(35(31,33)46)50-16(2)37/h8-9,12,20-21,24-28,42-46H,10-11,13-14H2,1-7H3/t20-,21+,24-,25-,26+,27-,28-,29+,30-,31+,32+,33+,34-,35-/m0/s1

InChI Key

QUIUAWAJVAZIOJ-ZDAAGFHHSA-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
Chukrasia tabularis	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
Prostaglandin skeleton
Steroid lactone
Eicosanoid
Hexacarboxylic acid or derivatives
12-hydroxysteroid
9-hydroxysteroid
8-hydroxysteroid
6-hydroxysteroid
Hydroxysteroid
12-alpha-hydroxysteroid
Oxosteroid
2-oxosteroid
3-oxasteroid
Steroid
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Oxane
Pyran
Fatty acyl
Cyclic alcohol
Furan
Heteroaromatic compound
Methyl ester
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
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	-3.1	ChemAxon
pKa (Strongest Acidic)	11.51	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	272.09 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	167.08 m³·mol⁻¹	ChemAxon
Polarizability	72.04 Å³	ChemAxon
Number of Rings	6	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

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

162881145

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate (NP0257997)

MOL for NP0257997 ([(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate)

3D MOL for NP0257997 ([(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate)

3D SDF for NP0257997 ([(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate)

3D-SDF for NP0257997 ([(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate)

PDB for NP0257997 ([(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate)

3D PDB for NP0257997 ([(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate)

SMILES for NP0257997 ([(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate)

INCHI for NP0257997 ([(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate)

Structure for NP0257997 ([(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate)

3D Structure for NP0257997 ([(1s,2r,3r,4r,5s,6s,10r,11r,12s,13s,14s,15r,17r,18s)-3,12,14-tris(acetyloxy)-6-(furan-3-yl)-2,4,11,13,17-pentahydroxy-18-(2-methoxy-2-oxoethyl)-5,15-dimethyl-8-oxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadecan-1-yl]methyl acetate)