NP-MRD: Showing NP-Card for Swietephragmin F (NP0074032)

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Record Information

Version

2.0

Created at

2022-04-28 19:13:51 UTC

Updated at

2022-04-28 19:13:51 UTC

NP-MRD ID

NP0074032

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Swietephragmin F

Description

(1S,4R,5R,10R,12S,14R,15S,16R,18R,19S,20R,22S)-12-ethyl-5-(furan-3-yl)-15,16-dihydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]Docos-8-en-22-yl (2E)-2-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. Swietephragmin F is found in Swietenia mahogani and Swietenia mahogany. Based on a literature review very few articles have been published on (1S,4R,5R,10R,12S,14R,15S,16R,18R,19S,20R,22S)-12-ethyl-5-(furan-3-yl)-15,16-dihydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁵,¹⁸.0¹,¹⁰.0⁴,⁹.0¹⁰,¹⁴.0¹⁶,²⁰]Docos-8-en-22-yl (2E)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221132D          

 47 54  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652304282221132D          

 47 54  0  0  1  0            999 V2000
    1.0061   -1.0590    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5413   -1.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2650   -2.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4537   -2.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2359   -3.4756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0814   -1.9859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1948   -1.2085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3403   -0.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1629   -0.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4778    0.1181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8498    0.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1469    0.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3894   -1.6582    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7368   -0.9962    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2648   -0.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821   -0.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -1.2836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8425   -2.0868    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4091   -2.6931    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4764   -2.4630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5820   -2.5416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1965   -1.6826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8526   -0.7884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5478   -1.1862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2761   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1463   -0.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2914   -2.9634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8450   -2.0242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5257   -1.1996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0066   -0.4322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8438   -0.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3902   -0.8805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1060    0.5199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9146    0.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7036   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7720   -2.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5770   -3.8264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3277   -4.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3086   -5.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0516   -3.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7563   -4.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4801   -3.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0707   -3.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1403   -3.5506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5265   -1.6635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7150   -0.3864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7343   -0.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  8 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  1 16  1  0  0  0  0
 14 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
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 23  1  1  0  0  0
 22 24  1  0  0  0  0
 13 24  1  1  0  0  0
 22 25  1  1  0  0  0
 25 26  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 28 35  1  0  0  0  0
 18 35  1  0  0  0  0
 28 36  1  6  0  0  0
 27 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 19 44  1  1  0  0  0
 18 45  1  1  0  0  0
 17 46  1  1  0  0  0
  1 47  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074032

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12O[C@@H]3[C@@]4(O)[C@@H](OC(=O)C(\C)=C\C)[C@]5(C)C[C@@]4(O)[C@@](C)([C@H]5CC(=O)OC)[C@]4(CC[C@@]5(C)[C@@H](OC(=O)C=C5[C@@]34O1)C1=COC=C1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C35H42O12/c1-8-18(3)25(38)44-26-29(5)17-31(39)30(6,20(29)14-22(36)41-7)32-12-11-28(4)21(15-23(37)43-24(28)19-10-13-42-16-19)35(32)27(34(26,31)40)45-33(9-2,46-32)47-35/h8,10,13,15-16,20,24,26-27,39-40H,9,11-12,14,17H2,1-7H3/b18-8+/t20-,24-,26-,27+,28+,29+,30+,31+,32-,33-,34-,35+/m0/s1

> <INCHI_KEY>
YXUIYDNZDJXDFI-WAAXGACWSA-N

> <FORMULA>
C35H42O12

> <MOLECULAR_WEIGHT>
654.709

> <EXACT_MASS>
654.267626792

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
66.2333414407379

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,5R,10R,12S,14R,15S,16R,18R,19S,20R,22S)-12-ethyl-5-(furan-3-yl)-15,16-dihydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.1^{15,18}.0^{1,10}.0^{4,9}.0^{10,14}.0^{16,20}]docos-8-en-22-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
3.9818185976666673

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.835609188399232

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.737338592665651

> <JCHEM_PKA_STRONGEST_BASIC>
-2.862689895130812

> <JCHEM_POLAR_SURFACE_AREA>
160.19

> <JCHEM_REFRACTIVITY>
160.79270000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5R,10R,12S,14R,15S,16R,18R,19S,20R,22S)-12-ethyl-5-(furan-3-yl)-15,16-dihydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.1^{15,18}.0^{1,10}.0^{4,9}.0^{10,14}.0^{16,20}]docos-8-en-22-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.878  -1.977   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.877  -3.149   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.361  -4.600   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.847  -4.879   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.440  -6.488   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.152  -3.707   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.364  -2.256   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.635  -1.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.171  -1.203   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.758   0.220   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.586   1.219   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.274   0.413   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.460  -3.095   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.109  -1.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.228  -0.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.580  -0.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.843  -2.396   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.173  -3.895   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.364  -5.027   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.623  -4.598   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.953  -4.744   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.233  -3.141   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.458  -1.472   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.889  -2.214   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.515  -3.129   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.273  -1.280   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.011  -5.532   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.044  -3.779   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.448  -2.239   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.346  -0.807   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.908  -0.490   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.928  -1.644   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      11.398   0.970   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.907   1.277   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.780  -4.831   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.774  -4.002   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.544  -7.143   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.945  -7.996   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.909  -9.535   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      11.296  -7.257   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.612  -8.057   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.963  -7.319   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.332  -5.717   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       5.862  -6.628   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       8.450  -3.105   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       6.935  -0.721   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       1.371  -0.262   0.000  0.00  0.00           C+0
CONECT    1    2    7   16   47                                             
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13    2   14   20   24                                             
CONECT   14   13   15   17   23                                             
CONECT   15   14   16                                                       
CONECT   16   15    1                                                       
CONECT   17   14   18   29   46                                             
CONECT   18   17   19   35   45                                             
CONECT   19   18   20   27   44                                             
CONECT   20   19   13   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22   14                                                       
CONECT   24   22   13                                                       
CONECT   25   22   26                                                       
CONECT   26   25                                                            
CONECT   27   19   28   37                                                  
CONECT   28   27   29   35   36                                             
CONECT   29   28   17   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   28   18                                                       
CONECT   36   28                                                            
CONECT   37   27   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   43                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40                                                            
CONECT   44   19                                                            
CONECT   45   18                                                            
CONECT   46   17                                                            
CONECT   47    1                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  108    0
END

View in JSmol

Synonyms

Value	Source
(1S,4R,5R,10R,12S,14R,15S,16R,18R,19S,20R,22S)-12-Ethyl-5-(furan-3-yl)-15,16-dihydroxy-19-(2-methoxy-2-oxoethyl)-4,18,20-trimethyl-7-oxo-6,11,13,21-tetraoxaheptacyclo[10.8.1.1,.0,.0,.0,.0,]docos-8-en-22-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₅H₄₂O₁₂

Average Mass

654.7090 Da

Monoisotopic Mass

654.26763 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@@]12O[C@@H]3[C@@]4(O)[C@@H](OC(=O)C(\C)=C\C)[C@]5(C)C[C@@]4(O)[C@@](C)([C@H]5CC(=O)OC)[C@]4(CC[C@@]5(C)[C@@H](OC(=O)C=C5[C@@]34O1)C1=COC=C1)O2

InChI Identifier

InChI=1S/C35H42O12/c1-8-18(3)25(38)44-26-29(5)17-31(39)30(6,20(29)14-22(36)41-7)32-12-11-28(4)21(15-23(37)43-24(28)19-10-13-42-16-19)35(32)27(34(26,31)40)45-33(9-2,46-32)47-35/h8,10,13,15-16,20,24,26-27,39-40H,9,11-12,14,17H2,1-7H3/b18-8+/t20-,24-,26-,27+,28+,29+,30+,31+,32-,33-,34-,35+/m0/s1

InChI Key

YXUIYDNZDJXDFI-WAAXGACWSA-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
Swietenia mahagoni	Plant	KNApSAcK
Swietenia mahogany	Plant	KNApSAcK

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
Naphthalene
Tricarboxylic acid or derivatives
Carboxylic acid orthoester
Dihydropyranone
Fatty acid ester
Ortho ester
Fatty acyl
Pyran
Meta-dioxane
Methyl ester
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Heteroaromatic compound
Cyclic alcohol
Furan
Meta-dioxolane
Orthocarboxylic acid derivative
Carboxylic acid ester
1,2-diol
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	3.16	ALOGPS
logP	3.98	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.74	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	160.19 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	160.79 m³·mol⁻¹	ChemAxon
Polarizability	66.23 Å³	ChemAxon
Number of Rings	8	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

162903336

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Swietephragmin F (NP0074032)

MOL for NP0074032 (Swietephragmin F)

3D MOL for NP0074032 (Swietephragmin F)

3D SDF for NP0074032 (Swietephragmin F)

3D-SDF for NP0074032 (Swietephragmin F)

PDB for NP0074032 (Swietephragmin F)

3D PDB for NP0074032 (Swietephragmin F)

SMILES for NP0074032 (Swietephragmin F)

INCHI for NP0074032 (Swietephragmin F)

Structure for NP0074032 (Swietephragmin F)

3D Structure for NP0074032 (Swietephragmin F)