NP-MRD: Showing NP-Card for (+)-Gypenoside LXIX (NP0072118)

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Record Information

Version

1.0

Created at

2022-04-28 17:30:05 UTC

Updated at

2022-04-28 17:30:05 UTC

NP-MRD ID

NP0072118

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Gypenoside LXIX

Description

(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-{[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-16-hydroxy-14-[(2S,4E)-6-hydroxy-6-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}hept-4-en-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. (+)-Gypenoside LXIX is found in Gynostemma pentaphyllum and Panax japonicus . It was first documented in 2022 (PMID: 35489815). Based on a literature review a significant number of articles have been published on (2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-{[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-16-hydroxy-14-[(2S,4E)-6-hydroxy-6-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}hept-4-en-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (PMID: 35489814) (PMID: 35489813) (PMID: 35489812) (PMID: 35489811).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219302D          

 76 83  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1838    0.8922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

166173  0  0  0  0  0  0  0  0999 V2000
    4.1707    0.1398    5.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2736   -0.9137    4.7229 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282219302D          

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    5.8717    1.8632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5914    2.6391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1232    3.2699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9354    3.1246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2157    2.3487    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6838    1.7180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9641    0.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7763    0.7969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0566    0.0209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8687   -0.1243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.4005    0.5064    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1202    1.2824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3081    1.4276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6520    1.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4641    1.7679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2126    0.3612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1490   -0.9002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5247   -0.6098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0278    2.2035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4672    3.7553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8429    4.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3748    4.6765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
  8 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 13 15  1  6  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 16 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 19 27  1  6  0  0  0
 28 27  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  6  0  0  0
 32 35  1  1  0  0  0
 31 36  1  6  0  0  0
 30 37  1  1  0  0  0
 37 38  1  0  0  0  0
 39 38  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 39 44  1  0  0  0  0
 42 45  1  1  0  0  0
 41 46  1  6  0  0  0
 40 47  1  6  0  0  0
 19 48  1  6  0  0  0
 11 49  1  1  0  0  0
  8 50  1  6  0  0  0
  5 51  1  6  0  0  0
  3 52  1  0  0  0  0
  3 53  1  0  0  0  0
  2 54  1  6  0  0  0
 55 54  1  6  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 55 60  1  0  0  0  0
 60 61  1  1  0  0  0
 62 61  1  6  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 62 67  1  0  0  0  0
 66 68  1  6  0  0  0
 68 69  1  0  0  0  0
 65 70  1  1  0  0  0
 64 71  1  6  0  0  0
 63 72  1  1  0  0  0
 59 73  1  6  0  0  0
 58 74  1  1  0  0  0
 57 75  1  6  0  0  0
 75 76  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072118

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)\C=C\C[C@](C)(O[C@@H]1O[C@H](CO[C@H]2OC[C@H](O)[C@@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(C)(C)[C@@H]3CC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C53H90O23/c1-48(2,68)13-9-14-53(8,76-46-42(67)38(63)36(61)28(73-46)22-70-44-40(65)33(58)25(57)21-69-44)23-10-16-52(7)32(23)24(56)18-30-50(5)15-12-31(49(3,4)29(50)11-17-51(30,52)6)74-47-43(39(64)35(60)27(20-55)72-47)75-45-41(66)37(62)34(59)26(19-54)71-45/h9,13,23-47,54-68H,10-12,14-22H2,1-8H3/b13-9+/t23-,24+,25-,26+,27+,28+,29-,30+,31-,32-,33+,34+,35+,36+,37-,38-,39-,40+,41+,42+,43+,44+,45-,46-,47-,50-,51+,52+,53-/m0/s1

> <INCHI_KEY>
XILVLMRCUFMKSW-ZXBVKUNMSA-N

> <FORMULA>
C53H90O23

> <MOLECULAR_WEIGHT>
1095.28

> <EXACT_MASS>
1094.587289158

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_ATOM_COUNT>
166

> <JCHEM_AVERAGE_POLARIZABILITY>
115.99559249205215

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
15

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(2S,4E)-2-[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-5-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-16-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-6-hydroxy-6-methylhept-4-en-2-yl]oxy}-6-({[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.64

> <JCHEM_LOGP>
-2.1926192360000023

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.186232852811997

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.752719698744606

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6486743719488306

> <JCHEM_POLAR_SURFACE_AREA>
377.29

> <JCHEM_REFRACTIVITY>
262.8753000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-2-{[(2S,4E)-2-[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-5-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-16-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-6-hydroxy-6-methylhept-4-en-2-yl]oxy}-6-({[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.342   6.553   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.557   6.309   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.977   7.735   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.922   8.951   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.342  10.377   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.768  10.958   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.916   9.797   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.762  11.804   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.828   4.148   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.255   4.728   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.465   6.254   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.892   6.834   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.108   5.889   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.897   4.363   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.470   3.783   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.260   2.257   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -8.113   3.418   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -8.534   6.469   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -6.102   8.359   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -7.529   8.940   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -7.739  10.465   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -9.166  11.046   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -9.377  12.571   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -8.161  13.516   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -6.734  12.936   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -6.524  11.410   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -8.371  15.042   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0     -10.803  13.151   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0     -10.382  10.100   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -0.396   6.038   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       1.764   0.984   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       2.331   0.781   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       8.601   0.361   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       7.241  -0.130   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      10.961   3.478   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      10.437   4.926   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      11.430   6.104   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      12.946   5.833   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      13.469   4.384   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      12.477   3.207   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      13.000   1.759   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      14.516   1.487   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      15.039   0.039   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      16.555  -0.232   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      17.548   0.945   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      17.024   2.394   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      15.508   2.665   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      18.017   3.571   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0      19.533   3.300   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0      19.064   0.674   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0      17.078  -1.680   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0      14.046  -1.138   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      14.985   4.113   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      13.939   7.010   0.000  0.00  0.00           O+0
HETATM   75  C   UNK     0      10.907   7.552   0.000  0.00  0.00           C+0
HETATM   76  O   UNK     0      11.900   8.729   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   54                                                  
CONECT    3    2    4   52   53                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   51                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   50                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   18   49                                             
CONECT   12   11   13   16                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    7                                                       
CONECT   15   13                                                            
CONECT   16   12   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   11                                                       
CONECT   19   16   20   27   48                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   19   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   28   34                                                  
CONECT   34   33                                                            
CONECT   35   32                                                            
CONECT   36   31                                                            
CONECT   37   30   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   44                                                  
CONECT   40   39   41   47                                                  
CONECT   41   40   42   46                                                  
CONECT   42   41   43   45                                                  
CONECT   43   42   44                                                       
CONECT   44   43   39                                                       
CONECT   45   42                                                            
CONECT   46   41                                                            
CONECT   47   40                                                            
CONECT   48   19                                                            
CONECT   49   11                                                            
CONECT   50    8                                                            
CONECT   51    5                                                            
CONECT   52    3                                                            
CONECT   53    3                                                            
CONECT   54    2   55                                                       
CONECT   55   54   56   60                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58   75                                                  
CONECT   58   57   59   74                                                  
CONECT   59   58   60   73                                                  
CONECT   60   59   55   61                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63   67                                                  
CONECT   63   62   64   72                                                  
CONECT   64   63   65   71                                                  
CONECT   65   64   66   70                                                  
CONECT   66   65   67   68                                                  
CONECT   67   66   62                                                       
CONECT   68   66   69                                                       
CONECT   69   68                                                            
CONECT   70   65                                                            
CONECT   71   64                                                            
CONECT   72   63                                                            
CONECT   73   59                                                            
CONECT   74   58                                                            
CONECT   75   57   76                                                       
CONECT   76   75                                                            
MASTER        0    0    0    0    0    0    0    0   76    0  166    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₃H₉₀O₂₃

Average Mass

1095.2800 Da

Monoisotopic Mass

1094.58729 Da

IUPAC Name

(2S,3R,4S,5S,6R)-2-{[(2S,4E)-2-[(1R,2R,5S,7R,10R,11R,14S,15R,16R)-5-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-16-hydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-6-hydroxy-6-methylhept-4-en-2-yl]oxy}-6-({[(2R,3R,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)(O)\C=C\C[C@](C)(O[C@@H]1O[C@H](CO[C@H]2OC[C@H](O)[C@@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]1[C@@]3(C)CC[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(C)(C)[C@@H]3CC[C@@]21C

InChI Identifier

InChI=1S/C53H90O23/c1-48(2,68)13-9-14-53(8,76-46-42(67)38(63)36(61)28(73-46)22-70-44-40(65)33(58)25(57)21-69-44)23-10-16-52(7)32(23)24(56)18-30-50(5)15-12-31(49(3,4)29(50)11-17-51(30,52)6)74-47-43(39(64)35(60)27(20-55)72-47)75-45-41(66)37(62)34(59)26(19-54)71-45/h9,13,23-47,54-68H,10-12,14-22H2,1-8H3/b13-9+/t23-,24+,25-,26+,27+,28+,29-,30+,31-,32-,33+,34+,35+,36+,37-,38-,39-,40+,41+,42+,43+,44+,45-,46-,47-,50-,51+,52+,53-/m0/s1

InChI Key

XILVLMRCUFMKSW-ZXBVKUNMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Gynostemma pentaphyllum	Plant	KNApSAcK
Panax Japonicus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Steroidal glycoside
25-hydroxysteroid
14-alpha-methylsteroid
Hydroxysteroid
12-hydroxysteroid
Steroid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Fatty acyl
Oxane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	-2.2	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	377.29 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	262.88 m³·mol⁻¹	ChemAxon
Polarizability	116 Å³	ChemAxon
Number of Rings	8	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

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

154496708

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen Z, Ye X, Zhang Z, Zhao Q, Xiang Y, Xu N, Wang Q, Pan Y, Guo X, Wang Z: Genetic diversity and selection signatures of four indigenous pig breeds from eastern China. Anim Genet. 2022 Apr 30. doi: 10.1111/age.13208. [PubMed:35489815 ]
Wu A, Fahey MT, Cui D, El-Behesy B, Story DA: An evaluation of the outcome metric 'days alive and at home' in older patients after hip fracture surgery. Anaesthesia. 2022 Apr 30. doi: 10.1111/anae.15742. [PubMed:35489814 ]
Martinez-Pizarro S: Prolotherapy with dextrose to reduce pain in osteoarthritis of the knee. Reumatol Clin (Engl Ed). 2022 Apr;18(4):251-252. doi: 10.1016/j.reumae.2020.08.002. Epub 2021 Apr 5. [PubMed:35489813 ]
Gryspeerdt E, Mutluoglu M, Rummens S, Van Wambeke P, Peers K: Wasting of the hand is not fate! A case of missed true neurogenic thoracic outlet syndrome. Reumatol Clin (Engl Ed). 2022 Apr;18(4):249-250. doi: 10.1016/j.reumae.2021.05.005. [PubMed:35489812 ]
Tezcan ME, Volkan O, Mercan R, Sen N, Yilmaz-Oner S: Familial mediterranean fever patients may have unmet needs for the treatments of exertional leg pain and enthesitis. Reumatol Clin (Engl Ed). 2022 Apr;18(4):227-230. doi: 10.1016/j.reumae.2021.02.009. [PubMed:35489811 ]

Showing NP-Card for (+)-Gypenoside LXIX (NP0072118)

MOL for NP0072118 ((+)-Gypenoside LXIX)

3D MOL for NP0072118 ((+)-Gypenoside LXIX)

3D SDF for NP0072118 ((+)-Gypenoside LXIX)

3D-SDF for NP0072118 ((+)-Gypenoside LXIX)

PDB for NP0072118 ((+)-Gypenoside LXIX)

3D PDB for NP0072118 ((+)-Gypenoside LXIX)

SMILES for NP0072118 ((+)-Gypenoside LXIX)

INCHI for NP0072118 ((+)-Gypenoside LXIX)

Structure for NP0072118 ((+)-Gypenoside LXIX)

3D Structure for NP0072118 ((+)-Gypenoside LXIX)