NP-MRD: Showing NP-Card for ajureptaside D (NP0040693)

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Record Information

Version

2.0

Created at

2021-06-20 22:47:12 UTC

Updated at

2021-06-30 00:14:45 UTC

NP-MRD ID

NP0040693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ajureptaside D

Provided By

JEOL Database JEOL Logo

Description

ajureptaside D is found in Ajuga reptans and Betonica officinalis . ajureptaside D was first documented in 2011 (Ono, M., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100473D          

 65 68  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212100473D          

 65 68  0  0  0  0            999 V2000
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   -3.2312   -2.0185    1.2391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6115   -2.3679   -0.1010 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5126   -1.5051   -0.7661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9570   -1.0786   -1.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278    0.2287   -2.2909 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3212    1.1090   -1.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2257    2.4610   -1.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4009    2.8614   -2.3561 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4961    2.9832   -1.4556 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7065    3.4255   -2.0957 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8191    3.4790   -1.0371 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5320    4.4564   -0.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    4.7867   -2.7843 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6811    5.1326   -3.5462 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3164    4.7353   -3.7291 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0745    6.0483   -4.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808    4.2204   -3.0008 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9998    4.1165   -3.9422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2669    0.9271   -0.0629 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.3699   -4.0991    1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4026   -3.1954    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7449   -1.0772    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2160   -1.6802   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4273   -2.5732   -0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1922   -1.7374   -2.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269    0.9271   -0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    2.1179   -3.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9990    2.6692   -2.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9001    2.5104   -0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7832    3.7242   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2690    4.4347    0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3600    5.5828   -2.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4279    5.9424   -4.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5415    4.1048   -4.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1979    5.9895   -4.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625    4.9447   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2856    3.6493   -3.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870    1.3803   -0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
  6  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  2  0  0  0  0
  2 35  1  0  0  0  0
  4  5  2  0  0  0  0
 22 23  1  0  0  0  0
 11 12  1  0  0  0  0
  8 17  1  0  0  0  0
 17 15  1  0  0  0  0
 15 13  1  0  0  0  0
 13 10  1  0  0  0  0
 10  9  1  0  0  0  0
  6 19  1  0  0  0  0
 35 22  1  0  0  0  0
 22 21  1  0  0  0  0
 21 20  1  0  0  0  0
 24 33  1  0  0  0  0
 33 31  1  0  0  0  0
 31 29  1  0  0  0  0
 29 26  1  0  0  0  0
 26 25  1  0  0  0  0
 25 24  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 20 19  2  0  0  0  0
 27 28  1  0  0  0  0
 35  6  1  0  0  0  0
 35 65  1  6  0  0  0
  9  8  1  0  0  0  0
  2  1  1  0  0  0  0
  6  7  1  1  0  0  0
 10 11  1  0  0  0  0
  8  7  1  0  0  0  0
 26 27  1  0  0  0  0
 24 23  1  0  0  0  0
  8 40  1  6  0  0  0
 13 45  1  1  0  0  0
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  1 36  1  0  0  0  0
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  1 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C([H])[C@@]3(O[C@@]4([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]4([H])O[H])C(=O)C([H])=C(C([H])([H])[H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O14/c1-7-4-10(24)21(35-20-17(30)15(28)13(26)9(6-23)33-20)2-3-31-18(11(7)21)34-19-16(29)14(27)12(25)8(5-22)32-19/h2-4,8-9,11-20,22-23,25-30H,5-6H2,1H3/t8-,9+,11+,12-,13+,14+,15-,16-,17+,18+,19+,20-,21-/m1/s1

> <INCHI_KEY>
VIEGIQFDBMKKSH-ZOFBVDLWSA-N

> <FORMULA>
C21H30O14

> <MOLECULAR_WEIGHT>
506.457

> <EXACT_MASS>
506.163555646

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.51744262496959

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aS,7aR)-7-methyl-4a-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-one

> <ALOGPS_LOGP>
-1.75

> <JCHEM_LOGP>
-3.5689284233333334

> <ALOGPS_LOGS>
-0.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.040237802828312

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.474942184857188

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847616110285

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
110.06010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aS,7aR)-7-methyl-4a-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,7aH-cyclopenta[c]pyran-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
    0.7296    3.0432    1.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3164    4.7353   -3.7291 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0745    6.0483   -4.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808    4.2204   -3.0008 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9998    4.1165   -3.9422 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1938   -2.7540    1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2690    4.4347    0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
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 15 16  1  0
 17 18  1  0
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  4  3  1  0
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 35  6  1  0
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  6  7  1  1
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 24 23  1  0
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  1 36  1  0
  1 37  1  0
  1 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       0.730   3.043   1.420  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.736   1.562   1.244  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.159   0.683   2.159  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.947  -0.648   1.573  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.383  -1.667   2.094  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.066  -0.565   0.311  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.341  -0.750   0.519  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.705  -1.845   1.366  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.379  -1.553   2.719  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.697  -2.648   3.598  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.129  -2.304   4.977  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.301  -2.244   4.924  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.215  -2.861   3.621  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.574  -3.971   4.442  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.709  -3.115   2.191  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.144  -3.182   2.196  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.231  -2.018   1.239  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.611  -2.368  -0.101  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.513  -1.505  -0.766  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.957  -1.079  -1.950  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.128   0.229  -2.291  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.321   1.109  -1.176  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.226   2.461  -1.645  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.401   2.861  -2.356  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.496   2.983  -1.456  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.707   3.426  -2.096  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.819   3.479  -1.037  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.532   4.456  -0.037  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.518   4.787  -2.784  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.681   5.133  -3.546  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.316   4.735  -3.729  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.075   6.048  -4.261  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.081   4.220  -3.001  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.000   4.117  -3.942  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.267   0.927  -0.063  0.00  0.00           C+0
HETATM   36  H   UNK     0       0.991   3.325   2.446  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.451   3.521   0.752  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.266   3.447   1.208  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.563   0.853   3.142  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.194  -2.754   1.028  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.182  -3.550   3.239  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.480  -1.322   5.311  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.401  -3.052   5.726  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.553  -1.939   4.027  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.719  -1.975   4.028  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.522  -4.133   4.260  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.370  -4.099   1.843  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.403  -3.195   1.252  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.745  -1.077   1.472  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.216  -1.680  -0.673  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.427  -2.573  -0.590  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.192  -1.737  -2.777  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.327   0.927  -0.770  0.00  0.00           H+0
HETATM   54  H   UNK     0       2.623   2.118  -3.133  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.999   2.669  -2.836  0.00  0.00           H+0
HETATM   56  H   UNK     0       5.900   2.510  -0.533  0.00  0.00           H+0
HETATM   57  H   UNK     0       6.783   3.724  -1.494  0.00  0.00           H+0
HETATM   58  H   UNK     0       6.269   4.435   0.598  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.360   5.583  -2.047  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.428   5.942  -4.035  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.542   4.105  -4.599  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.198   5.989  -4.692  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.763   4.945  -2.241  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.286   3.649  -3.464  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.687   1.380  -0.365  0.00  0.00           H+0
CONECT    1    2   36   37   38                                             
CONECT    2    3   35    1                                                  
CONECT    3    4    2   39                                                  
CONECT    4    6    3    5                                                  
CONECT    5    4                                                            
CONECT    6    4   19   35    7                                             
CONECT    7    6    8                                                       
CONECT    8   17    9    7   40                                             
CONECT    9   10    8                                                       
CONECT   10   13    9   11   41                                             
CONECT   11   12   10   42   43                                             
CONECT   12   11   44                                                       
CONECT   13   14   15   10   45                                             
CONECT   14   13   46                                                       
CONECT   15   16   17   13   47                                             
CONECT   16   15   48                                                       
CONECT   17   18    8   15   49                                             
CONECT   18   17   50                                                       
CONECT   19    6   20   51                                                  
CONECT   20   21   19   52                                                  
CONECT   21   22   20                                                       
CONECT   22   23   35   21   53                                             
CONECT   23   22   24                                                       
CONECT   24   33   25   23   54                                             
CONECT   25   26   24                                                       
CONECT   26   29   25   27   55                                             
CONECT   27   28   26   56   57                                             
CONECT   28   27   58                                                       
CONECT   29   31   26   30   59                                             
CONECT   30   29   60                                                       
CONECT   31   33   29   32   61                                             
CONECT   32   31   62                                                       
CONECT   33   24   31   34   63                                             
CONECT   34   33   64                                                       
CONECT   35    2   22    6   65                                             
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    3                                                            
CONECT   40    8                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   22                                                            
CONECT   54   24                                                            
CONECT   55   26                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   29                                                            
CONECT   60   30                                                            
CONECT   61   31                                                            
CONECT   62   32                                                            
CONECT   63   33                                                            
CONECT   64   34                                                            
CONECT   65   35                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  136    0
END

RDKit          3D

65 68  0  0  0  0  0  0  0  0999 V2000
    0.7296    3.0432    1.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363    1.5622    1.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589    0.6832    2.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9470   -0.6481    1.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3825   -1.6673    2.0940 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0662   -0.5652    0.3114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3408   -0.7503    0.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052   -1.8446    1.3662 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3787   -1.5527    2.7188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6972   -2.6484    3.5980 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1288   -2.3037    4.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3008   -2.2443    4.9236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2147   -2.8605    3.6208 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5736   -3.9711    4.4424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7087   -3.1150    2.1914 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1436   -3.1817    2.1959 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2312   -2.0185    1.2391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6115   -2.3679   -0.1010 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5126   -1.5051   -0.7661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9570   -1.0786   -1.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278    0.2287   -2.2909 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3212    1.1090   -1.1757 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2257    2.4610   -1.6453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4009    2.8614   -2.3561 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4961    2.9832   -1.4556 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7065    3.4255   -2.0957 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8191    3.4790   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320    4.4564   -0.0366 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181    4.7867   -2.7843 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6811    5.1326   -3.5462 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3164    4.7353   -3.7291 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0745    6.0483   -4.2607 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0808    4.2204   -3.0008 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9998    4.1165   -3.9422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2669    0.9271   -0.0629 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9908    3.3248    2.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4511    3.5212    0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2655    3.4467    1.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631    0.8529    3.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938   -2.7540    1.0278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1820   -3.5496    3.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4803   -1.3221    5.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4006   -3.0524    5.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5530   -1.9394    4.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7194   -1.9753    4.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5219   -4.1326    4.2600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3699   -4.0991    1.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4026   -3.1954    1.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7449   -1.0772    1.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2160   -1.6802   -0.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4273   -2.5732   -0.5895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1922   -1.7374   -2.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269    0.9271   -0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6233    2.1179   -3.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9990    2.6692   -2.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9001    2.5104   -0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7832    3.7242   -1.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2690    4.4347    0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3600    5.5828   -2.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4279    5.9424   -4.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5415    4.1048   -4.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1979    5.9895   -4.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625    4.9447   -2.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2856    3.6493   -3.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870    1.3803   -0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
 15 16  1  0
 17 18  1  0
  6  4  1  0
  4  3  1  0
  3  2  2  0
  2 35  1  0
  4  5  2  0
 22 23  1  0
 11 12  1  0
  8 17  1  0
 17 15  1  0
 15 13  1  0
 13 10  1  0
 10  9  1  0
  6 19  1  0
 35 22  1  0
 22 21  1  0
 21 20  1  0
 24 33  1  0
 33 31  1  0
 31 29  1  0
 29 26  1  0
 26 25  1  0
 25 24  1  0
 29 30  1  0
 31 32  1  0
 33 34  1  0
 20 19  2  0
 27 28  1  0
 35  6  1  0
 35 65  1  6
  9  8  1  0
  2  1  1  0
  6  7  1  1
 10 11  1  0
  8  7  1  0
 26 27  1  0
 24 23  1  0
  8 40  1  6
 13 45  1  1
 14 46  1  0
 15 47  1  6
 16 48  1  0
 17 49  1  1
 18 50  1  0
 11 42  1  0
 11 43  1  0
 10 41  1  6
 12 44  1  0
 22 53  1  1
 20 52  1  0
 19 51  1  0
  3 39  1  0
 24 54  1  6
 29 59  1  1
 30 60  1  0
 31 61  1  6
 32 62  1  0
 33 63  1  1
 34 64  1  0
 27 56  1  0
 27 57  1  0
 26 55  1  6
 28 58  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₀O₁₄

Average Mass

506.4570 Da

Monoisotopic Mass

506.16356 Da

IUPAC Name

(1S,4aS,7aR)-7-methyl-4a-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-5-one

Traditional Name

(1S,4aS,7aR)-7-methyl-4a-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,7aH-cyclopenta[c]pyran-5-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C([H])[C@@]3(O[C@@]4([H])O[C@@]([H])(C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]4([H])O[H])C(=O)C([H])=C(C([H])([H])[H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C21H30O14/c1-7-4-10(24)21(35-20-17(30)15(28)13(26)9(6-23)33-20)2-3-31-18(11(7)21)34-19-16(29)14(27)12(25)8(5-22)32-19/h2-4,8-9,11-20,22-23,25-30H,5-6H2,1H3/t8-,9+,11+,12-,13+,14+,15-,16-,17+,18+,19+,20-,21-/m1/s1

InChI Key

VIEGIQFDBMKKSH-ZOFBVDLWSA-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
Ajuga reptans	JEOL database	Ono, M., et al, Chem. Pharm. Bull. 59, 1065 (2011)
Betonica officinalis	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	-1.8	ALOGPS
logP	-3.6	ChemAxon
logS	-0.84	ALOGPS
pKa (Strongest Acidic)	11.47	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	110.06 m³·mol⁻¹	ChemAxon
Polarizability	48.52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Ono, M., et al. (2011). Ono, M., et al, Chem. Pharm. Bull. 59, 1065 (2011). Chem. Pharm. Bull..

Showing NP-Card for ajureptaside D (NP0040693)

MOL for NP0040693 (ajureptaside D)

3D MOL for NP0040693 (ajureptaside D)

3D SDF for NP0040693 (ajureptaside D)

3D-SDF for NP0040693 (ajureptaside D)

PDB for NP0040693 (ajureptaside D)

3D PDB for NP0040693 (ajureptaside D)

SMILES for NP0040693 (ajureptaside D)

INCHI for NP0040693 (ajureptaside D)

Structure for NP0040693 (ajureptaside D)

3D Structure for NP0040693 (ajureptaside D)