NP-MRD: Showing NP-Card for (1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid (NP0171554)

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Record Information

Version

2.0

Created at

2022-09-03 08:07:04 UTC

Updated at

2022-09-03 08:07:04 UTC

NP-MRD ID

NP0171554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid

Description

(1R,4S,7S,9S,10S,13R,15S)-7-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2Z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5,5-dicarboxylic acid belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid is found in Gnaphalium sylvaticum. Based on a literature review very few articles have been published on (1R,4S,7S,9S,10S,13R,15S)-7-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2Z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecane-5,5-dicarboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032210072D          

 43 47  0  0  1  0            999 V2000
    0.0435   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566   -0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794    0.4660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3435    1.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2893    0.0832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5946    0.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    1.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582    0.4175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7638    0.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4487    1.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9514    2.0120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308    1.4662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4599    1.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1914    0.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4246    1.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206   -0.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8140   -0.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
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  9 13  1  0  0  0  0
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  5 39  1  0  0  0  0
 39 40  1  6  0  0  0
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 41 42  1  0  0  0  0
  2 42  1  0  0  0  0
 42 43  1  6  0  0  0
  5 43  1  6  0  0  0
M  END

     RDKit          3D

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   -5.0875   -0.9020   -1.1636 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032210072D          

 43 47  0  0  1  0            999 V2000
    0.0435   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4794    0.4660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3435    1.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2893    0.0832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5946    0.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    1.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582    0.4175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7638    0.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4487    1.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9514    2.0120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6308    1.4662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4599    1.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1914    0.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4246    1.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206   -0.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0719   -0.7999    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6288   -1.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4344   -1.2307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6831   -0.4441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4887   -0.2662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7374    0.5205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5430    0.6984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0456   -0.8749    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8512   -0.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7969   -1.6615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3537   -2.2702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9913   -1.8394    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7426   -2.6260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2994   -3.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1050   -3.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0507   -4.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2451   -4.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6076   -4.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4132   -4.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7095   -0.3691    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4700   -1.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883   -0.5708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6431   -1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7976   -1.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377   -0.9152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8140   -0.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 17 36  1  0  0  0  0
 36 37  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
  5 39  1  0  0  0  0
 39 40  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
  2 42  1  0  0  0  0
 42 43  1  6  0  0  0
  5 43  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0171554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1C[C@@]2(C)[C@@H]3CC[C@@H]4C[C@@]3(CC[C@@H]2C(C1)(C(O)=O)C(O)=O)[C@@H](O)C4=C

> <INCHI_IDENTIFIER>
InChI=1S/C31H44O12/c1-5-14(2)25(36)43-23-22(34)21(33)18(13-32)42-26(23)41-17-11-29(4)19-7-6-16-10-30(19,24(35)15(16)3)9-8-20(29)31(12-17,27(37)38)28(39)40/h5,16-24,26,32-35H,3,6-13H2,1-2,4H3,(H,37,38)(H,39,40)/b14-5-/t16-,17+,18-,19+,20+,21-,22+,23-,24+,26-,29+,30-/m1/s1

> <INCHI_KEY>
PUCBVOBXLMBRDL-IVURCJJDSA-N

> <FORMULA>
C31H44O12

> <MOLECULAR_WEIGHT>
608.681

> <EXACT_MASS>
608.283276857

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
62.94836884630249

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S,7S,9S,10S,13R,15S)-7-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2Z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5,5-dicarboxylic acid

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
1.9800028183333318

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.174390924875824

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4919940866205774

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7380948552845709

> <JCHEM_POLAR_SURFACE_AREA>
200.27999999999997

> <JCHEM_REFRACTIVITY>
148.35490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,7S,9S,10S,13R,15S)-7-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2Z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5,5-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       0.081  -0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.599  -0.263   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.761   0.870   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.508   2.389   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.273   0.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.843   1.624   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.354   1.935   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.389   0.779   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.892   1.111   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.304   2.535   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.243   3.756   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.778   2.737   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.192   1.938   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.557   1.226   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.126   3.476   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.932  -0.025   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.468  -1.493   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.507  -2.629   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.011  -2.297   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.475  -0.829   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.979  -0.497   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.443   0.972   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      15.947   1.304   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      15.018  -1.633   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.522  -1.301   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.554  -3.101   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.594  -4.238   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.050  -3.434   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.586  -4.902   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      13.626  -6.038   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      15.129  -5.706   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.161  -7.506   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.658  -7.839   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.201  -8.643   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.705  -8.311   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.964  -1.825   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.924  -0.689   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.477  -2.163   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.392  -1.066   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.934  -2.642   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.356  -2.939   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.310  -1.708   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.386  -0.839   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   42                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   39   43                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   37                                                  
CONECT    9    8   10   13   16                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   19   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   17   37                                                       
CONECT   37   36    8   38   39                                             
CONECT   38   37                                                            
CONECT   39   37    5   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41    2   43                                                  
CONECT   43   42    5                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
(1R,4S,7S,9S,10S,13R,15S)-7-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2Z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0,.0,]hexadecane-5,5-dicarboxylate	Generator

Chemical Formula

C₃₁H₄₄O₁₂

Average Mass

608.6810 Da

Monoisotopic Mass

608.28328 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1C[C@@]2(C)[C@@H]3CC[C@@H]4C[C@@]3(CC[C@@H]2C(C1)(C(O)=O)C(O)=O)[C@@H](O)C4=C

InChI Identifier

InChI=1S/C31H44O12/c1-5-14(2)25(36)43-23-22(34)21(33)18(13-32)42-26(23)41-17-11-29(4)19-7-6-16-10-30(19,24(35)15(16)3)9-8-20(29)31(12-17,27(37)38)28(39)40/h5,16-24,26,32-35H,3,6-13H2,1-2,4H3,(H,37,38)(H,39,40)/b14-5-/t16-,17+,18-,19+,20+,21-,22+,23-,24+,26-,29+,30-/m1/s1

InChI Key

PUCBVOBXLMBRDL-IVURCJJDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gnaphalium sylvaticum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Kaurane diterpenoid
Saccharolipid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Monosaccharide
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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	1.14	ALOGPS
logP	1.98	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	2.49	ChemAxon
pKa (Strongest Basic)	-0.74	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	148.35 m³·mol⁻¹	ChemAxon
Polarizability	62.95 Å³	ChemAxon
Number of Rings	5	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9832068

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11657330

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid (NP0171554)

MOL for NP0171554 ((1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid)

3D MOL for NP0171554 ((1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid)

3D SDF for NP0171554 ((1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid)

3D-SDF for NP0171554 ((1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid)

PDB for NP0171554 ((1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid)

3D PDB for NP0171554 ((1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid)

SMILES for NP0171554 ((1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid)

INCHI for NP0171554 ((1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid)

Structure for NP0171554 ((1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid)

3D Structure for NP0171554 ((1r,4s,7s,9s,10s,13r,15s)-7-{[(2r,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2z)-2-methylbut-2-enoyl]oxy}oxan-2-yl]oxy}-15-hydroxy-9-methyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5,5-dicarboxylic acid)