NP-MRD: Showing NP-Card for komaroveside B (NP0040462)

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Record Information

Version

2.0

Created at

2021-06-20 22:37:12 UTC

Updated at

2021-06-30 00:14:23 UTC

NP-MRD ID

NP0040462

Secondary Accession Numbers

None

Natural Product Identification

Common Name

komaroveside B

Provided By

JEOL Database JEOL Logo

Description

(3E)-4-[(1R,4S,5S,6S)-5-hydroxy-2,2,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-oxabicyclo[4.1.0]Heptan-1-yl]but-3-en-2-one belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. komaroveside B is found in Cardamine komarovii. komaroveside B was first documented in 2011 (Lee, I. K., et al.). Based on a literature review very few articles have been published on (3E)-4-[(1R,4S,5S,6S)-5-hydroxy-2,2,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-oxabicyclo[4.1.0]Heptan-1-yl]but-3-en-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100373D          

 58 60  0  0  0  0            999 V2000
    4.8367   -6.7486   -2.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -5.6822   -2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139   -5.6358   -3.8610 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5393   -4.6988   -1.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242   -3.7316   -1.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2596   -2.7022   -0.8715 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1265   -3.0719    0.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8847   -2.8499   -0.1828 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0666   -4.1052   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1357   -1.6493    0.3517 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1765   -1.6828    1.7857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6745   -0.3017   -0.1739 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2171    0.8360    0.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9800    2.5781    1.4055 C   0  0  2  0  0  0  0  0  0  0  0  0
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 21 19  1  0  0  0  0
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  6 26  1  0  0  0  0
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  2  3  2  0  0  0  0
  8  9  1  6  0  0  0
 17 18  1  0  0  0  0
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  6  7  1  0  0  0  0
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M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306212100373D          

 58 60  0  0  0  0            999 V2000
    4.8367   -6.7486   -2.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -5.6822   -2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139   -5.6358   -3.8610 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7202   -0.8185   -2.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4271   -6.5089   -1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5208   -6.8222   -3.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3289   -7.7038   -2.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0929   -4.7932   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0824   -3.6815   -2.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5819   -4.0385   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674   -4.2444    0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844   -5.0034   -0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9218   -1.7295    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784   -1.9706    2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659   -0.1681   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6357    0.1468    1.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375    0.3747   -0.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687    2.0086   -2.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1131    3.4641    0.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972    1.8558    2.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7014    3.8966    2.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9544    3.1343    0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022    1.8553    2.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5226   -0.4276    0.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5564    0.7488   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5498   -1.6962    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8288   -0.3379   -0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9296   -1.9992   -1.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361    0.2248   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340   -1.4142   -3.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848   -0.8992   -2.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  1  0  0  0  0
 19 16  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
 25 26  1  0  0  0  0
 12 10  1  0  0  0  0
 10  8  1  0  0  0  0
  8  6  1  0  0  0  0
  6 26  1  0  0  0  0
  6  5  1  6  0  0  0
 19 20  1  0  0  0  0
  5  4  2  0  0  0  0
 21 22  1  0  0  0  0
  4  2  1  0  0  0  0
 23 24  1  0  0  0  0
  2  1  1  0  0  0  0
  2  3  2  0  0  0  0
  8  9  1  6  0  0  0
 17 18  1  0  0  0  0
 26 27  1  1  0  0  0
 25 12  1  0  0  0  0
 26 28  1  0  0  0  0
 14 23  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
  6  7  1  0  0  0  0
 23 21  1  0  0  0  0
  8  7  1  0  0  0  0
 16 17  1  0  0  0  0
 14 13  1  0  0  0  0
 14 40  1  1  0  0  0
 19 45  1  6  0  0  0
 20 46  1  0  0  0  0
 21 47  1  1  0  0  0
 22 48  1  0  0  0  0
 23 49  1  6  0  0  0
 24 50  1  0  0  0  0
 17 42  1  0  0  0  0
 17 43  1  0  0  0  0
 16 41  1  1  0  0  0
 18 44  1  0  0  0  0
 25 51  1  0  0  0  0
 25 52  1  0  0  0  0
 12 39  1  6  0  0  0
 10 37  1  1  0  0  0
  5 33  1  0  0  0  0
  4 32  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
 27 53  1  0  0  0  0
 27 54  1  0  0  0  0
 27 55  1  0  0  0  0
 28 56  1  0  0  0  0
 28 57  1  0  0  0  0
 28 58  1  0  0  0  0
 11 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040462

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O9/c1-9(21)5-6-19-17(2,3)7-10(15(25)18(19,4)28-19)26-16-14(24)13(23)12(22)11(8-20)27-16/h5-6,10-16,20,22-25H,7-8H2,1-4H3/b6-5+/t10-,11+,12+,13-,14+,15-,16+,18-,19+/m0/s1

> <INCHI_KEY>
DFFPNQTWISHGLR-XZOMIJAFSA-N

> <FORMULA>
C19H30O9

> <MOLECULAR_WEIGHT>
402.44

> <EXACT_MASS>
402.188982546

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.4738981727826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-4-[(1R,4S,5S,6S)-5-hydroxy-2,2,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-oxabicyclo[4.1.0]heptan-1-yl]but-3-en-2-one

> <ALOGPS_LOGP>
-0.51

> <JCHEM_LOGP>
-1.1188166509999997

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.832429034958029

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.1388421664998

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835533691584

> <JCHEM_POLAR_SURFACE_AREA>
149.21

> <JCHEM_REFRACTIVITY>
95.6901

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-4-[(1R,4S,5S,6S)-5-hydroxy-2,2,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-oxabicyclo[4.1.0]heptan-1-yl]but-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
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   -1.7551    1.0390   -0.6938 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9752    2.7134    0.0410 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2442    3.8672    1.9805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4797    2.3008    1.3791 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9968    2.2488    2.7306 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2054   -0.2641   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -1.2971   -1.0512 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3805   -1.3346   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7202   -0.8185   -2.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4271   -6.5089   -1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0929   -4.7932   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3169    0.2532   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4972    1.8558    2.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9544    3.1343    0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022    1.8553    2.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5226   -0.4276    0.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5564    0.7488   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5498   -1.6962    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8288   -0.3379   -0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9296   -1.9992   -1.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361    0.2248   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340   -1.4142   -3.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848   -0.8992   -2.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  1  0
 19 16  1  0
 16 15  1  0
 15 14  1  0
 25 26  1  0
 12 10  1  0
 10  8  1  0
  8  6  1  0
  6 26  1  0
  6  5  1  6
 19 20  1  0
  5  4  2  0
 21 22  1  0
  4  2  1  0
 23 24  1  0
  2  1  1  0
  2  3  2  0
  8  9  1  6
 17 18  1  0
 26 27  1  1
 25 12  1  0
 26 28  1  0
 14 23  1  0
 10 11  1  0
 12 13  1  0
  6  7  1  0
 23 21  1  0
  8  7  1  0
 16 17  1  0
 14 13  1  0
 14 40  1  1
 19 45  1  6
 20 46  1  0
 21 47  1  1
 22 48  1  0
 23 49  1  6
 24 50  1  0
 17 42  1  0
 17 43  1  0
 16 41  1  1
 18 44  1  0
 25 51  1  0
 25 52  1  0
 12 39  1  6
 10 37  1  1
  5 33  1  0
  4 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
 11 38  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       4.837  -6.749  -2.506  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.813  -5.682  -2.789  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.214  -5.636  -3.861  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.539  -4.699  -1.706  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.624  -3.732  -1.876  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.260  -2.702  -0.872  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.127  -3.072   0.514  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.885  -2.850  -0.183  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.067  -4.105  -0.313  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.136  -1.649   0.352  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.177  -1.683   1.786  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.675  -0.302  -0.174  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.217   0.836   0.578  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.206   0.985   0.623  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.755   1.039  -0.694  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.180   1.205  -0.679  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.707   1.143  -2.119  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.128   1.087  -2.164  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.555   2.539  -0.011  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.975   2.713   0.041  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.980   2.578   1.406  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.244   3.867   1.980  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.480   2.301   1.379  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.997   2.249   2.731  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.205  -0.264  -0.110  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.874  -1.297  -1.051  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.380  -1.335  -0.715  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.720  -0.819  -2.514  0.00  0.00           C+0
HETATM   29  H   UNK     0       5.427  -6.509  -1.618  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.521  -6.822  -3.356  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.329  -7.704  -2.351  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.093  -4.793  -0.780  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.082  -3.682  -2.821  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.582  -4.038  -1.192  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.567  -4.244   0.569  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.684  -5.003  -0.410  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.922  -1.730   0.076  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.078  -1.971   2.024  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.366  -0.168  -1.216  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.636   0.147   1.183  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.638   0.375  -0.123  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.369   2.009  -2.699  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.317   0.253  -2.625  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.461   1.748  -1.519  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.150   3.380  -0.588  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.113   3.464   0.658  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.497   1.856   2.049  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.701   3.897   2.796  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.954   3.134   0.896  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.102   1.855   2.669  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.523  -0.428   0.929  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.556   0.749  -0.351  0.00  0.00           H+0
HETATM   53  H   UNK     0       4.550  -1.696   0.306  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.829  -0.338  -0.797  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.930  -1.999  -1.391  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.036   0.225  -2.625  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.334  -1.414  -3.199  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.685  -0.899  -2.861  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2   32                                                  
CONECT    5    6    4   33                                                  
CONECT    6    8   26    5    7                                             
CONECT    7    6    8                                                       
CONECT    8   10    6    9    7                                             
CONECT    9    8   34   35   36                                             
CONECT   10   12    8   11   37                                             
CONECT   11   10   38                                                       
CONECT   12   10   25   13   39                                             
CONECT   13   12   14                                                       
CONECT   14   15   23   13   40                                             
CONECT   15   16   14                                                       
CONECT   16   19   15   17   41                                             
CONECT   17   18   16   42   43                                             
CONECT   18   17   44                                                       
CONECT   19   21   16   20   45                                             
CONECT   20   19   46                                                       
CONECT   21   19   22   23   47                                             
CONECT   22   21   48                                                       
CONECT   23   24   14   21   49                                             
CONECT   24   23   50                                                       
CONECT   25   26   12   51   52                                             
CONECT   26   25    6   27   28                                             
CONECT   27   26   53   54   55                                             
CONECT   28   26   56   57   58                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36    9                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   14                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
CONECT   43   17                                                            
CONECT   44   18                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   27                                                            
CONECT   54   27                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   28                                                            
CONECT   58   28                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  120    0
END

RDKit          3D

58 60  0  0  0  0  0  0  0  0999 V2000
    4.8367   -6.7486   -2.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -5.6822   -2.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139   -5.6358   -3.8610 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5393   -4.6988   -1.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242   -3.7316   -1.8764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2596   -2.7022   -0.8715 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1265   -3.0719    0.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8847   -2.8499   -0.1828 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0666   -4.1052   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1357   -1.6493    0.3517 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1765   -1.6828    1.7857 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6745   -0.3017   -0.1739 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2171    0.8360    0.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2061    0.9854    0.6226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7551    1.0390   -0.6938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1799    1.2048   -0.6789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7069    1.1426   -2.1190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1284    1.0865   -2.1643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5547    2.5386   -0.0108 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9752    2.7134    0.0410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800    2.5781    1.4055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2442    3.8672    1.9805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4797    2.3008    1.3791 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9968    2.2488    2.7306 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2054   -0.2641   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8745   -1.2971   -1.0512 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3805   -1.3346   -0.7148 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7202   -0.8185   -2.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4271   -6.5089   -1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5208   -6.8222   -3.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3289   -7.7038   -2.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0929   -4.7932   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0824   -3.6815   -2.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5819   -4.0385   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5674   -4.2444    0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6844   -5.0034   -0.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9218   -1.7295    0.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0784   -1.9706    2.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659   -0.1681   -1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6357    0.1468    1.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375    0.3747   -0.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687    2.0086   -2.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3169    0.2532   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4611    1.7478   -1.5192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    3.3796   -0.5879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1131    3.4641    0.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4972    1.8558    2.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7014    3.8966    2.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9544    3.1343    0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022    1.8553    2.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5226   -0.4276    0.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5564    0.7488   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5498   -1.6962    0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8288   -0.3379   -0.7969 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9296   -1.9992   -1.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361    0.2248   -2.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340   -1.4142   -3.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848   -0.8992   -2.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 19  1  0
 19 16  1  0
 16 15  1  0
 15 14  1  0
 25 26  1  0
 12 10  1  0
 10  8  1  0
  8  6  1  0
  6 26  1  0
  6  5  1  6
 19 20  1  0
  5  4  2  0
 21 22  1  0
  4  2  1  0
 23 24  1  0
  2  1  1  0
  2  3  2  0
  8  9  1  6
 17 18  1  0
 26 27  1  1
 25 12  1  0
 26 28  1  0
 14 23  1  0
 10 11  1  0
 12 13  1  0
  6  7  1  0
 23 21  1  0
  8  7  1  0
 16 17  1  0
 14 13  1  0
 14 40  1  1
 19 45  1  6
 20 46  1  0
 21 47  1  1
 22 48  1  0
 23 49  1  6
 24 50  1  0
 17 42  1  0
 17 43  1  0
 16 41  1  1
 18 44  1  0
 25 51  1  0
 25 52  1  0
 12 39  1  6
 10 37  1  1
  5 33  1  0
  4 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
 11 38  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₃₀O₉

Average Mass

402.4400 Da

Monoisotopic Mass

402.18898 Da

IUPAC Name

(3E)-4-[(1R,4S,5S,6S)-5-hydroxy-2,2,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-oxabicyclo[4.1.0]heptan-1-yl]but-3-en-2-one

Traditional Name

(3E)-4-[(1R,4S,5S,6S)-5-hydroxy-2,2,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7-oxabicyclo[4.1.0]heptan-1-yl]but-3-en-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H30O9/c1-9(21)5-6-19-17(2,3)7-10(15(25)18(19,4)28-19)26-16-14(24)13(23)12(22)11(8-20)27-16/h5-6,10-16,20,22-25H,7-8H2,1-4H3/b6-5+/t10-,11+,12+,13-,14+,15-,16+,18-,19+/m0/s1

InChI Key

DFFPNQTWISHGLR-XZOMIJAFSA-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
Cardamine komarovii	JEOL database	Lee, I. K., et al., Chem. Pharm. Bull., 59, 773 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Oxepane
Monosaccharide
Oxane
Acryloyl-group
Cyclic alcohol
Enone
Alpha,beta-unsaturated ketone
Ketone
Secondary alcohol
Acetal
Organoheterocyclic compound
Ether
Oxirane
Oxacycle
Dialkyl ether
Polyol
Organic oxide
Hydrocarbon derivative
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	-0.51	ALOGPS
logP	-1.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.14	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	95.69 m³·mol⁻¹	ChemAxon
Polarizability	41.47 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

53248455

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee, I. K., et al. (2011). Lee, I. K., et al., Chem. Pharm. Bull., 59, 773 (2011). Chem. Pharm. Bull..

Showing NP-Card for komaroveside B (NP0040462)

MOL for NP0040462 (komaroveside B)

3D MOL for NP0040462 (komaroveside B)

3D SDF for NP0040462 (komaroveside B)

3D-SDF for NP0040462 (komaroveside B)

PDB for NP0040462 (komaroveside B)

3D PDB for NP0040462 (komaroveside B)

SMILES for NP0040462 (komaroveside B)

INCHI for NP0040462 (komaroveside B)

Structure for NP0040462 (komaroveside B)

3D Structure for NP0040462 (komaroveside B)