NP-MRD: Showing NP-Card for Mahagonin (NP0066525)

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Record Information

Version

2.0

Created at

2022-04-28 10:46:54 UTC

Updated at

2022-04-28 10:46:54 UTC

NP-MRD ID

NP0066525

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mahagonin

Description

Methyl (2S)-2-{[(1R,5R,6S,13R,14R,16S,17S)-6-(furan-3-yl)-14,17-dihydroxy-16-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-1,5,15,15-tetramethyl-8-oxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadeca-2(11),9-dien-17-yl]oxy}-2-[(1R,5R,6R,13S,14S,16R)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadeca-2(11),9-dien-16-yl]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. Mahagonin is found in Swietenia mahagoni JACQ. . Based on a literature review very few articles have been published on methyl (2S)-2-{[(1R,5R,6S,13R,14R,16S,17S)-6-(furan-3-yl)-14,17-dihydroxy-16-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-1,5,15,15-tetramethyl-8-oxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadeca-2(11),9-dien-17-yl]oxy}-2-[(1R,5R,6R,13S,14S,16R)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadeca-2(11),9-dien-16-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212462D          

 70 79  0  0  1  0            999 V2000
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  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
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  8  7  1  6  0  0  0
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  9 10  1  1  0  0  0
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  6 46  1  0  0  0  0
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 62 67  1  1  0  0  0
  2 68  1  0  0  0  0
  2 69  1  0  0  0  0
  1 70  1  1  0  0  0
M  END

     RDKit          3D

134143  0  0  0  0  0  0  0  0999 V2000
   -2.0810   -5.3496   -0.4747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1545   -4.0598    0.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282212462D          

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M  END
> <DATABASE_ID>
NP0066525

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H](O)[C@H]1C(C)(C)[C@H](O)[C@H]2CC3=C(CC[C@@]4(C)[C@H](OC(=O)C=C34)C3=COC=C3)[C@]1(C)[C@@]2(O)O[C@@H]([C@@H]1C(C)(C)[C@@H](O)[C@@H]2CC3=C(CC[C@@]4(C)[C@@H](OC(=O)C=C34)C3=COC=C3)[C@]1(C)C2=O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C54H64O16/c1-48(2)39(37(57)46(61)64-9)53(8)31-12-16-51(6)33(22-36(56)69-45(51)26-14-18-67-24-26)28(31)20-34(43(48)60)54(53,63)70-38(47(62)65-10)40-49(3,4)41(58)29-19-27-30(52(40,7)42(29)59)11-15-50(5)32(27)21-35(55)68-44(50)25-13-17-66-23-25/h13-14,17-18,21-24,29,34,37-41,43-45,57-58,60,63H,11-12,15-16,19-20H2,1-10H3/t29-,34+,37+,38-,39-,40+,41-,43+,44-,45+,50+,51+,52-,53-,54-/m0/s1

> <INCHI_KEY>
MKYFEWODHCPJRO-LANTXVFKSA-N

> <FORMULA>
C54H64O16

> <MOLECULAR_WEIGHT>
969.09

> <EXACT_MASS>
968.419435981

$$$$

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      -0.748  -5.033   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.064  -6.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.557  -7.872   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.937  -8.556   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.396  -8.063   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.080  -6.684   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.587  -5.224   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.207  -4.541   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.570  -6.514   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.123  -5.492   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.018  -7.246   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.754  -5.787   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.179  -3.937   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.204  -2.568   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.497  -3.598   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.001  -2.018   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.503  -6.607   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.559  -8.146   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.687  -9.195   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.226  -9.139   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.275  -8.011   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.219  -6.472   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.091  -5.423   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.552  -5.480   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.932  -7.518   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.105  -7.405   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.837  -3.842   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.435  -3.922   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.907  -3.470   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.035  -4.519   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.691  -6.020   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.819  -7.068   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.291  -6.616   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.578  -7.574   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      10.635  -5.115   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       9.507  -4.066   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.851  -2.565   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.839  -1.404   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.630  -0.083   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      11.131  -0.427   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.268  -1.961   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.221  -2.978   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       4.517 -10.696   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       1.752  -9.948   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.882 -10.029   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -5.616  -6.586   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -6.300  -5.206   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -7.837  -5.108   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -8.630  -3.712   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -8.690  -6.390   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -8.006  -7.770   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -6.470  -7.868   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -5.786  -9.248   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -4.249  -9.346   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -7.249  -9.183   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -8.860  -9.052   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -8.324 -10.496   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -9.531 -11.452   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0     -10.813 -10.599   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0     -10.398  -9.116   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -2.271 -10.177   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       0.185  -9.501   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      -0.454 -10.961   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0      -1.984 -11.132   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0       0.459 -12.201   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      -0.158 -13.612   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0       1.794  -8.965   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0       1.690  -5.376   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       1.807  -5.944   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      -0.501  -3.132   0.000  0.00  0.00           O+0
CONECT    1    2    8   70                                                  
CONECT    2    1    3   68   69                                             
CONECT    3    2    4   62                                                  
CONECT    4    3    5    9   61                                             
CONECT    5    4    6   54                                                  
CONECT    6    5    7   46                                                  
CONECT    7    6    8                                                       
CONECT    8    7    1    9                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17   12   18   24                                                  
CONECT   18   17   19   44   45                                             
CONECT   19   18   20   43                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   17   25   27                                             
CONECT   25   24   20   26                                                  
CONECT   26   25                                                            
CONECT   27   24                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   36   42                                             
CONECT   31   30   22   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   30   37                                                  
CONECT   37   36   38   41                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   37                                                       
CONECT   42   30                                                            
CONECT   43   19                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46    6   47   52                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   52   56                                                  
CONECT   52   51   46   53   55                                             
CONECT   53   52   54                                                       
CONECT   54   53    5                                                       
CONECT   55   52                                                            
CONECT   56   51   57   60                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   56                                                       
CONECT   61    4                                                            
CONECT   62    3   63   67                                                  
CONECT   63   62   64   65                                                  
CONECT   64   63                                                            
CONECT   65   63   66                                                       
CONECT   66   65                                                            
CONECT   67   62                                                            
CONECT   68    2                                                            
CONECT   69    2                                                            
CONECT   70    1                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  158    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2S)-2-{[(1R,5R,6S,13R,14R,16S,17S)-6-(furan-3-yl)-14,17-dihydroxy-16-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-1,5,15,15-tetramethyl-8-oxo-7-oxatetracyclo[11.3.1.0,.0,]heptadeca-2(11),9-dien-17-yl]oxy}-2-[(1R,5R,6R,13S,14S,16R)-6-(furan-3-yl)-14-hydroxy-1,5,15,15-tetramethyl-8,17-dioxo-7-oxatetracyclo[11.3.1.0,.0,]heptadeca-2(11),9-dien-16-yl]acetic acid	Generator

Chemical Formula

C₅₄H₆₄O₁₆

Average Mass

969.0900 Da

Monoisotopic Mass

968.41944 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H](O)[C@H]1C(C)(C)[C@H](O)[C@H]2CC3=C(CC[C@@]4(C)[C@H](OC(=O)C=C34)C3=COC=C3)[C@]1(C)[C@@]2(O)O[C@@H]([C@@H]1C(C)(C)[C@@H](O)[C@@H]2CC3=C(CC[C@@]4(C)[C@@H](OC(=O)C=C34)C3=COC=C3)[C@]1(C)C2=O)C(=O)OC

InChI Identifier

InChI=1S/C54H64O16/c1-48(2)39(37(57)46(61)64-9)53(8)31-12-16-51(6)33(22-36(56)69-45(51)26-14-18-67-24-26)28(31)20-34(43(48)60)54(53,63)70-38(47(62)65-10)40-49(3,4)41(58)29-19-27-30(52(40,7)42(29)59)11-15-50(5)32(27)21-35(55)68-44(50)25-13-17-66-23-25/h13-14,17-18,21-24,29,34,37-41,43-45,57-58,60,63H,11-12,15-16,19-20H2,1-10H3/t29-,34+,37+,38-,39-,40+,41-,43+,44-,45+,50+,51+,52-,53-,54-/m0/s1

InChI Key

MKYFEWODHCPJRO-LANTXVFKSA-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 JACQ.	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

Mexicanolide
Limonoid skeleton
Naphthopyran
Tetracarboxylic acid or derivatives
Naphthalene
Cyclohexenone
Dihydropyranone
Pyran
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Furan
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

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

162955513

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Mahagonin (NP0066525)

MOL for NP0066525 (Mahagonin)

3D MOL for NP0066525 (Mahagonin)

3D SDF for NP0066525 (Mahagonin)

3D-SDF for NP0066525 (Mahagonin)

PDB for NP0066525 (Mahagonin)

3D PDB for NP0066525 (Mahagonin)

SMILES for NP0066525 (Mahagonin)

INCHI for NP0066525 (Mahagonin)

Structure for NP0066525 (Mahagonin)

3D Structure for NP0066525 (Mahagonin)