NP-MRD: Showing NP-Card for 10-hydroxy-18-methoxylbetaenone (NP0029161)

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Record Information

Version

2.0

Created at

2021-06-19 20:51:45 UTC

Updated at

2021-06-29 23:56:21 UTC

NP-MRD ID

NP0029161

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-hydroxy-18-methoxylbetaenone

Provided By

JEOL Database JEOL Logo

Description

(2S,3R,4R,4aR,5R,7R,8aR)-3-[(2S)-butan-2-yl]-2,7,8a-trihydroxy-4-[(2E)-3-methoxyprop-2-enoyl]-2,4,5,7-tetramethyl-decahydronaphthalen-1-one belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. 10-hydroxy-18-methoxylbetaenone is found in Microsphaeropsis Species. 10-hydroxy-18-methoxylbetaenone was first documented in 2000 (Brauers, G., et al.). Based on a literature review very few articles have been published on (2S,3R,4R,4aR,5R,7R,8aR)-3-[(2S)-butan-2-yl]-2,7,8a-trihydroxy-4-[(2E)-3-methoxyprop-2-enoyl]-2,4,5,7-tetramethyl-decahydronaphthalen-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122513D          

 64 65  0  0  0  0            999 V2000
    4.9061   -3.8837   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8652   -3.0383    0.3072 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3525   -1.8267   -0.5197 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5062   -0.8766   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0945   -1.1593    0.1752 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3549   -0.0952    1.2793 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7726    1.3217    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3814   -0.5877    2.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876    0.0473    2.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6  9  1  0  0  0  0
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M  END

     RDKit          3D

 64 65  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192122513D          

 64 65  0  0  0  0            999 V2000
    4.9061   -3.8837   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8652   -3.0383    0.3072 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.0945   -1.1593    0.1752 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.7726    1.3217    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3814   -0.5877    2.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876    0.0473    2.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1924    0.3341    3.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744   -0.1934    1.4531 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -3.7152    1.3299    3.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
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  6  9  1  0  0  0  0
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 13 14  1  0  0  0  0
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  6  7  1  0  0  0  0
 17 18  1  0  0  0  0
  6  8  1  1  0  0  0
 20 11  1  0  0  0  0
 11 12  1  6  0  0  0
 21 23  1  6  0  0  0
 14 16  1  6  0  0  0
  5  3  1  0  0  0  0
 23 25  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  3  2  1  0  0  0  0
 23 24  2  0  0  0  0
  2  1  1  0  0  0  0
  5 21  1  0  0  0  0
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 22 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029161

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1(C(=O)[C@@]2(O[H])C([H])([H])[C@@](O[H])(C([H])([H])[H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]2([H])[C@@](C(=O)C(\[H])=C(/[H])OC([H])([H])[H])(C([H])([H])[H])[C@@]1([H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O6/c1-8-13(2)16-20(5,15(23)9-10-28-7)17-14(3)11-19(4,25)12-22(17,27)18(24)21(16,6)26/h9-10,13-14,16-17,25-27H,8,11-12H2,1-7H3/b10-9+/t13-,14+,16+,17+,19+,20+,21-,22+/m0/s1

> <INCHI_KEY>
ONZDNBGTAVEQQN-GSUHUVJFSA-N

> <FORMULA>
C22H36O6

> <MOLECULAR_WEIGHT>
396.524

> <EXACT_MASS>
396.251188879

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
43.25249494167475

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4R,4aR,5R,7R,8aR)-3-[(2S)-butan-2-yl]-2,7,8a-trihydroxy-4-[(2E)-3-methoxyprop-2-enoyl]-2,4,5,7-tetramethyl-decahydronaphthalen-1-one

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.5162369266666675

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.193846647937363

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.450707057898335

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8248971025388654

> <JCHEM_POLAR_SURFACE_AREA>
104.06000000000002

> <JCHEM_REFRACTIVITY>
107.15629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,4aR,5R,7R,8aR)-3-[(2S)-butan-2-yl]-2,7,8a-trihydroxy-4-[(2E)-3-methoxyprop-2-enoyl]-2,4,5,7-tetramethyl-tetrahydro-3H-naphthalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 65  0  0  0  0  0  0  0  0999 V2000
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 22 58  1  0
 22 59  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       4.906  -3.884  -0.418  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.865  -3.038   0.307  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.353  -1.827  -0.520  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.506  -0.877  -0.849  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.095  -1.159   0.175  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.355  -0.095   1.279  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.773   1.322   0.884  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.381  -0.588   2.155  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.088   0.047   2.132  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.192   0.334   3.332  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.274  -0.193   1.453  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.622  -1.556   1.701  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.293   0.738   2.149  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.705   0.583   1.587  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.673   1.538   2.288  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.136  -0.758   1.849  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.693   0.824   0.079  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.687  -0.069  -0.689  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.811   0.318  -2.167  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.236   0.053  -0.088  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.921  -0.771  -0.826  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.494   0.124  -1.967  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.389  -2.071  -1.529  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.392  -2.174  -2.759  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.132  -3.214  -0.727  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.878  -4.156  -1.323  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.461  -5.266  -0.773  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.271  -5.474   0.623  0.00  0.00           C+0
HETATM   29  H   UNK     0       4.544  -4.197  -1.401  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.126  -4.785   0.164  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.847  -3.341  -0.547  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.020  -3.696   0.547  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.290  -2.707   1.260  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.016  -2.252  -1.473  0.00  0.00           H+0
HETATM   35  H   UNK     0       4.169   0.004  -1.399  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.243  -1.368  -1.494  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.033  -0.549   0.052  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.691  -1.997   0.756  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.984   1.880   0.377  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.672   1.342   0.268  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.027   1.903   1.781  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.212  -0.191   3.035  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.541  -1.566   2.053  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.962   1.782   2.063  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.325   0.495   3.220  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.381   2.584   2.147  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.715   1.330   3.363  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.692   1.410   1.907  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.058  -0.840   1.539  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.462   1.880  -0.121  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.698   0.636  -0.321  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.028  -1.106  -0.588  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.862   0.323  -2.479  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.411   1.321  -2.349  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.307  -0.388  -2.827  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.027   1.115  -0.204  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.974   1.029  -1.593  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.724   0.453  -2.667  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.230  -0.410  -2.578  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.094  -3.257   0.325  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.113  -4.129  -2.384  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.797  -6.392   0.901  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.210  -5.607   0.857  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.699  -4.650   1.203  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1   32   33                                             
CONECT    3    5    4    2   34                                             
CONECT    4    3   35   36   37                                             
CONECT    5    3    6   21   38                                             
CONECT    6    9    7    8    5                                             
CONECT    7    6   39   40   41                                             
CONECT    8    6   42                                                       
CONECT    9    6   11   10                                                  
CONECT   10    9                                                            
CONECT   11    9   13   20   12                                             
CONECT   12   11   43                                                       
CONECT   13   11   14   44   45                                             
CONECT   14   13   15   17   16                                             
CONECT   15   14   46   47   48                                             
CONECT   16   14   49                                                       
CONECT   17   14   18   50   51                                             
CONECT   18   20   19   17   52                                             
CONECT   19   18   53   54   55                                             
CONECT   20   21   18   56   11                                             
CONECT   21   20   23    5   22                                             
CONECT   22   21   57   58   59                                             
CONECT   23   21   25   24                                                  
CONECT   24   23                                                            
CONECT   25   23   26   60                                                  
CONECT   26   27   25   61                                                  
CONECT   27   26   28                                                       
CONECT   28   27   62   63   64                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    2                                                            
CONECT   33    2                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    4                                                            
CONECT   38    5                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43   12                                                            
CONECT   44   13                                                            
CONECT   45   13                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   19                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   22                                                            
CONECT   58   22                                                            
CONECT   59   22                                                            
CONECT   60   25                                                            
CONECT   61   26                                                            
CONECT   62   28                                                            
CONECT   63   28                                                            
CONECT   64   28                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  130    0
END

RDKit          3D

64 65  0  0  0  0  0  0  0  0999 V2000
    4.9061   -3.8837   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8652   -3.0383    0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3525   -1.8267   -0.5197 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5062   -0.8766   -0.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0945   -1.1593    0.1752 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3549   -0.0952    1.2793 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7726    1.3217    0.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3814   -0.5877    2.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0876    0.0473    2.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1924    0.3341    3.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744   -0.1934    1.4531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6224   -1.5556    1.7007 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2932    0.7383    2.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    0.5830    1.5871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6729    1.5380    2.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1356   -0.7578    1.8490 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    0.8244    0.0791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6867   -0.0694   -0.6885 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8112    0.3179   -2.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2364    0.0533   -0.0875 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9208   -0.7713   -0.8260 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4945    0.1240   -1.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3887   -2.0706   -1.5289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3918   -2.1738   -2.7592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1321   -3.2142   -0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775   -4.1559   -1.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4612   -5.2656   -0.7731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2711   -5.4740    0.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5437   -4.1972   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1258   -4.7849    0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8468   -3.3413   -0.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204   -3.6958    0.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2897   -2.7071    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0162   -2.2523   -1.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1686    0.0039   -1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2426   -1.3679   -1.4936 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0327   -0.5489    0.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6910   -1.9973    0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9838    1.8802    0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6720    1.3418    0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0272    1.9029    1.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2124   -0.1906    3.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5410   -1.5663    2.0533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9617    1.7817    2.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253    0.4952    3.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3815    2.5840    2.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7152    1.3299    3.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6925    1.4097    1.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0575   -0.8399    1.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4623    1.8798   -0.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6984    0.6361   -0.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0279   -1.1062   -0.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8620    0.3226   -2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4105    1.3205   -2.3489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3071   -0.3875   -2.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0273    1.1145   -0.2039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9745    1.0288   -1.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7239    0.4526   -2.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2298   -0.4102   -2.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0943   -3.2567    0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -4.1294   -2.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7970   -6.3920    0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2099   -5.6075    0.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6991   -4.6498    1.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  9  1  0
 26 27  1  0
  9 11  1  0
 27 28  1  0
 20 21  1  0
  9 10  2  0
 20 18  1  0
 20 56  1  1
 11 13  1  0
 18 19  1  0
 13 14  1  0
 14 15  1  0
 14 17  1  0
  6  7  1  0
 17 18  1  0
  6  8  1  1
 20 11  1  0
 11 12  1  6
 21 23  1  6
 14 16  1  6
  5  3  1  0
 23 25  1  0
  3  4  1  0
  5  6  1  0
  3  2  1  0
 23 24  2  0
  2  1  1  0
  5 21  1  0
  5 38  1  1
 25 26  2  0
 21 22  1  0
 13 44  1  0
 13 45  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  6
 25 60  1  0
 26 61  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 19 53  1  0
 19 54  1  0
 19 55  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
 12 43  1  0
 16 49  1  0
  3 34  1  6
  4 35  1  0
  4 36  1  0
  4 37  1  0
  2 32  1  0
  2 33  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 22 57  1  0
 22 58  1  0
 22 59  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₆O₆

Average Mass

396.5240 Da

Monoisotopic Mass

396.25119 Da

IUPAC Name

(2S,3R,4R,4aR,5R,7R,8aR)-3-[(2S)-butan-2-yl]-2,7,8a-trihydroxy-4-[(2E)-3-methoxyprop-2-enoyl]-2,4,5,7-tetramethyl-decahydronaphthalen-1-one

Traditional Name

(2S,3R,4R,4aR,5R,7R,8aR)-3-[(2S)-butan-2-yl]-2,7,8a-trihydroxy-4-[(2E)-3-methoxyprop-2-enoyl]-2,4,5,7-tetramethyl-tetrahydro-3H-naphthalen-1-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1(C(=O)[C@@]2(O[H])C([H])([H])[C@@](O[H])(C([H])([H])[H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]2([H])[C@@](C(=O)C(\[H])=C(/[H])OC([H])([H])[H])(C([H])([H])[H])[C@@]1([H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H36O6/c1-8-13(2)16-20(5,15(23)9-10-28-7)17-14(3)11-19(4,25)12-22(17,27)18(24)21(16,6)26/h9-10,13-14,16-17,25-27H,8,11-12H2,1-7H3/b10-9+/t13-,14+,16+,17+,19+,20+,21-,22+/m0/s1

InChI Key

ONZDNBGTAVEQQN-GSUHUVJFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Microsphaeropsis Species	JEOL database	Brauers, G., et al, J. Nat. Prod. 63, 739 (2000)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Acyloins

Alternative Parents

Substituents

Acyloin
Vinylogous ester
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Cyclic alcohol
Acryloyl-group
Ketone
Polyol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.25	ALOGPS
logP	2.52	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	107.16 m³·mol⁻¹	ChemAxon
Polarizability	43.25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

57642757

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588198

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Brauers, G., et al. (2000). Brauers, G., et al, J. Nat. Prod. 63, 739 (2000). J. Nat. Prod..

Showing NP-Card for 10-hydroxy-18-methoxylbetaenone (NP0029161)

MOL for NP0029161 (10-hydroxy-18-methoxylbetaenone)

3D MOL for NP0029161 (10-hydroxy-18-methoxylbetaenone)

3D SDF for NP0029161 (10-hydroxy-18-methoxylbetaenone)

3D-SDF for NP0029161 (10-hydroxy-18-methoxylbetaenone)

PDB for NP0029161 (10-hydroxy-18-methoxylbetaenone)

3D PDB for NP0029161 (10-hydroxy-18-methoxylbetaenone)

SMILES for NP0029161 (10-hydroxy-18-methoxylbetaenone)

INCHI for NP0029161 (10-hydroxy-18-methoxylbetaenone)

Structure for NP0029161 (10-hydroxy-18-methoxylbetaenone)

3D Structure for NP0029161 (10-hydroxy-18-methoxylbetaenone)