NP-MRD: Showing NP-Card for (1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+ (NP0039039)

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Record Information

Version

2.0

Created at

2021-06-20 21:34:49 UTC

Updated at

2021-06-30 00:12:09 UTC

NP-MRD ID

NP0039039

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+

Provided By

JEOL Database JEOL Logo

Description

(3AS)-1,4beta-Dimethyl-3abeta,6beta-dihydroxy-7beta-[1-(beta-D-glucopyranosyloxy)-1-methylethyl]-2,3,3a,4,5,6,7,8-octahydroazulene-2-one belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+ is found in Daucus carota L. (1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+ was first documented in 2010 (Fu, H.-w. et al.). Based on a literature review very few articles have been published on (3aS)-1,4beta-Dimethyl-3abeta,6beta-dihydroxy-7beta-[1-(beta-D-glucopyranosyloxy)-1-methylethyl]-2,3,3a,4,5,6,7,8-octahydroazulene-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123343D          

 64 66  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202123343D          

 64 66  0  0  0  0            999 V2000
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    1.1073   -0.1047    3.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0370    2.1578    3.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0554   -0.9033   -4.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725   -2.5168   -2.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930   -2.6218   -2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1562   -2.1406    0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1138   -4.1682   -0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6273   -4.3482   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5433   -4.2854    1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
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 11 10  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 26 28  1  0  0  0  0
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  2  3  2  0  0  0  0
 29 30  2  0  0  0  0
  2  1  1  0  0  0  0
 13 14  1  0  0  0  0
 24 25  1  0  0  0  0
 10 19  1  0  0  0  0
 26 27  1  6  0  0  0
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  5  6  1  0  0  0  0
  6  9  1  1  0  0  0
 19 17  1  0  0  0  0
  6  7  1  0  0  0  0
  3  4  1  0  0  0  0
  6  8  1  0  0  0  0
 17 15  1  0  0  0  0
 21 22  1  0  0  0  0
 10  9  1  0  0  0  0
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 22 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039039

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC(C([H])([H])[H])(C([H])([H])[H])[C@@]2([H])C([H])([H])C3=C(C(=O)C([H])([H])[C@]3(O[H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@@]2([H])O[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O9/c1-9-5-13(23)12(6-11-10(2)14(24)7-21(9,11)28)20(3,4)30-19-18(27)17(26)16(25)15(8-22)29-19/h9,12-13,15-19,22-23,25-28H,5-8H2,1-4H3/t9-,12-,13+,15+,16+,17-,18+,19-,21-/m0/s1

> <INCHI_KEY>
MTYMLDACNLVKSY-RDZGJUGJSA-N

> <FORMULA>
C21H34O9

> <MOLECULAR_WEIGHT>
430.494

> <EXACT_MASS>
430.220282675

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
43.935867534391726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,6R,8S,8aS)-6,8a-dihydroxy-3,8-dimethyl-5-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-1,2,4,5,6,7,8,8a-octahydroazulen-2-one

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-1.2916109826666673

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.097079540313864

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.196763344468343

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8704763205027524

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
105.2152

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4S,6R,7S)-3a,6-dihydroxy-1,4-dimethyl-7-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-3,4,5,6,7,8-hexahydroazulen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
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 22 55  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.910   0.056   1.794  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.167  -1.097   1.235  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.558  -1.313   0.057  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.489  -0.319  -1.072  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.946   0.227  -1.247  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.964   1.772  -1.546  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.394   2.300  -1.762  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.135   2.162  -2.789  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.296   2.500  -0.482  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.978   2.711   0.758  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.137   1.503   1.493  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.816   1.702   2.738  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.050   0.338   3.402  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.937   0.438   4.511  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.996   2.627   3.651  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.680   2.877   4.883  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.731   3.950   2.930  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.136   4.758   3.741  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.102   3.696   1.562  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.042   4.951   0.878  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.783  -0.653  -2.205  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.515  -0.324  -3.565  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.620  -2.176  -2.067  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.508  -2.729  -0.629  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.064  -4.167  -0.637  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.047  -2.690  -0.087  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.817  -3.398  -0.980  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.076  -3.297   1.321  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.955  -2.317   2.028  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.405  -2.475   3.154  0.00  0.00           O+0
HETATM   31  H   UNK     0      -1.463   0.376   2.740  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.912   0.920   1.125  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.952  -0.220   1.984  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.188   0.497  -0.868  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.854  -0.778  -1.999  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.448   0.109  -0.281  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.410   3.396  -1.778  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.063   1.980  -0.955  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.825   1.944  -2.704  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.574   1.818  -3.727  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.892   1.790  -2.729  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.050   3.254  -2.857  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.950   3.178   0.566  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.801   2.151   2.548  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.107  -0.105   3.740  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.487  -0.363   2.682  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.635   1.203   5.047  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.037   2.158   3.906  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.180   3.609   5.304  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.661   4.523   2.828  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.415   5.495   3.160  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.912   3.294   1.687  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.335   4.715  -0.026  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.841  -0.418  -2.032  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.055  -0.903  -4.131  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.773  -2.517  -2.676  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.493  -2.622  -2.564  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.156  -2.141   0.034  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.114  -4.168  -0.952  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.031  -4.624   0.356  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.510  -4.811  -1.328  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.627  -4.348  -0.912  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.879  -3.315   1.859  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.543  -4.285   1.323  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2   29    3    1                                                  
CONECT    3   26    2    4                                                  
CONECT    4    5    3   34   35                                             
CONECT    5    4   21    6   36                                             
CONECT    6    5    9    7    8                                             
CONECT    7    6   37   38   39                                             
CONECT    8    6   40   41   42                                             
CONECT    9    6   10                                                       
CONECT   10   11   19    9   43                                             
CONECT   11   12   10                                                       
CONECT   12   15   11   13   44                                             
CONECT   13   14   12   45   46                                             
CONECT   14   13   47                                                       
CONECT   15   12   16   17   48                                             
CONECT   16   15   49                                                       
CONECT   17   18   19   15   50                                             
CONECT   18   17   51                                                       
CONECT   19   20   10   17   52                                             
CONECT   20   19   53                                                       
CONECT   21   23    5   22   54                                             
CONECT   22   21   55                                                       
CONECT   23   24   21   56   57                                             
CONECT   24   23   25   26   58                                             
CONECT   25   24   59   60   61                                             
CONECT   26    3   28   27   24                                             
CONECT   27   26   62                                                       
CONECT   28   26   29   63   64                                             
CONECT   29   28    2   30                                                  
CONECT   30   29                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    4                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42    8                                                            
CONECT   43   10                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   23                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   25                                                            
CONECT   61   25                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   28                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  132    0
END

RDKit          3D

64 66  0  0  0  0  0  0  0  0999 V2000
   -1.9097    0.0558    1.7937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1667   -1.0972    1.2346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5579   -1.3129    0.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4890   -0.3192   -1.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9463    0.2269   -1.2467 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9639    1.7722   -1.5458 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3944    2.2997   -1.7618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1354    2.1620   -2.7888 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2955    2.4997   -0.4818 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9779    2.7113    0.7584 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1369    1.5029    1.4928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8161    1.7016    2.7379 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0505    0.3383    3.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9366    0.4382    4.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9955    2.6268    3.6507 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6798    2.8773    4.8831 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307    3.9495    2.9298 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1356    4.7577    3.7406 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1015    3.6960    1.5617 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0422    4.9509    0.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -0.6531   -2.2054 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5148   -0.3239   -3.5654 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6196   -2.1762   -2.0666 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5075   -2.7291   -0.6287 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0641   -4.1669   -0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0466   -2.6903   -0.0867 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8169   -3.3978   -0.9803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0755   -3.2969    1.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9554   -2.3171    2.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4048   -2.4749    3.1539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    0.3757    2.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9116    0.9200    1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -0.2203    1.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1879    0.4971   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543   -0.7775   -1.9991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482    0.1085   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096    3.3956   -1.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0625    1.9801   -0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246    1.9442   -2.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5738    1.8178   -3.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8922    1.7900   -2.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0502    3.2543   -2.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9499    3.1784    0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8005    2.1513    2.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1073   -0.1047    3.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4868   -0.3626    2.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6346    1.2033    5.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0370    2.1578    3.9060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803    3.6094    5.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6605    4.5231    2.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150    5.4949    3.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9118    3.2944    1.6868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3354    4.7150   -0.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8408   -0.4184   -2.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0554   -0.9033   -4.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7725   -2.5168   -2.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930   -2.6218   -2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1562   -2.1406    0.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1138   -4.1682   -0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0314   -4.6242    0.3557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5104   -4.8108   -1.3283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273   -4.3482   -0.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8785   -3.3148    1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5433   -4.2854    1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 15 12  1  0
  4  5  1  0
 12 11  1  0
 23 21  1  0
  5 21  1  0
  3 26  1  0
 11 10  1  0
 15 16  1  0
 17 18  1  0
 19 20  1  0
 26 28  1  0
 28 29  1  0
 29  2  1  0
  2  3  2  0
 29 30  2  0
  2  1  1  0
 13 14  1  0
 24 25  1  0
 10 19  1  0
 26 27  1  6
 26 24  1  0
  5  6  1  0
  6  9  1  1
 19 17  1  0
  6  7  1  0
  3  4  1  0
  6  8  1  0
 17 15  1  0
 21 22  1  0
 10  9  1  0
 12 13  1  0
 10 43  1  6
 15 48  1  1
 16 49  1  0
 17 50  1  6
 18 51  1  0
 19 52  1  1
 20 53  1  0
 13 45  1  0
 13 46  1  0
 12 44  1  6
 14 47  1  0
 24 58  1  1
  4 34  1  0
  4 35  1  0
 23 56  1  0
 23 57  1  0
  5 36  1  1
 21 54  1  1
 28 63  1  0
 28 64  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
 27 62  1  0
  7 37  1  0
  7 38  1  0
  7 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 22 55  1  0
M  END

View in JSmol

Synonyms

Value	Source
(3AS)-1,4b-dimethyl-3abeta,6b-dihydroxy-7b-[1-(b-D-glucopyranosyloxy)-1-methylethyl]-2,3,3a,4,5,6,7,8-octahydroazulene-2-one	Generator
(3AS)-1,4β-dimethyl-3abeta,6β-dihydroxy-7β-[1-(β-D-glucopyranosyloxy)-1-methylethyl]-2,3,3a,4,5,6,7,8-octahydroazulene-2-one	Generator

Chemical Formula

C₂₁H₃₄O₉

Average Mass

430.4940 Da

Monoisotopic Mass

430.22028 Da

IUPAC Name

(5S,6R,8S,8aS)-6,8a-dihydroxy-3,8-dimethyl-5-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-1,2,4,5,6,7,8,8a-octahydroazulen-2-one

Traditional Name

(3aS,4S,6R,7S)-3a,6-dihydroxy-1,4-dimethyl-7-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-3,4,5,6,7,8-hexahydroazulen-2-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(OC(C([H])([H])[H])(C([H])([H])[H])[C@@]2([H])C([H])([H])C3=C(C(=O)C([H])([H])[C@]3(O[H])[C@@]([H])(C([H])([H])[H])C([H])([H])[C@@]2([H])O[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C21H34O9/c1-9-5-13(23)12(6-11-10(2)14(24)7-21(9,11)28)20(3,4)30-19-18(27)17(26)16(25)15(8-22)29-19/h9,12-13,15-19,22-23,25-28H,5-8H2,1-4H3/t9-,12-,13+,15+,16+,17-,18+,19-,21-/m0/s1

InChI Key

MTYMLDACNLVKSY-RDZGJUGJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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, 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
Daucus carota	JEOL database	Fu, H.-w. et al, Chem. Pharm. Bull. 58, 125 (2010)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Guaiane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Acetal
Organoheterocyclic compound
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.64	ALOGPS
logP	-1.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.22 m³·mol⁻¹	ChemAxon
Polarizability	43.94 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

45102164

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fu, H.-w. et al. (2010). Fu, H.-w. et al, Chem. Pharm. Bull. 58, 125 (2010). Chem. Pharm. Bull..

Showing NP-Card for (1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+ (NP0039039)

MOL for NP0039039 ((1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+)

3D MOL for NP0039039 ((1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+)

3D SDF for NP0039039 ((1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+)

3D-SDF for NP0039039 ((1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+)

PDB for NP0039039 ((1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+)

3D PDB for NP0039039 ((1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+)

SMILES for NP0039039 ((1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+)

INCHI for NP0039039 ((1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+)

Structure for NP0039039 ((1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+)

3D Structure for NP0039039 ((1beta,7beta,8beta,10beta)-1,8,11-trihydroxy-4-guaien-3-one-11-O-beta-D-g+)