NP-MRD: Showing NP-Card for gymnemic acid iii (NP0291618)

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Record Information

Version

2.0

Created at

2022-09-09 22:46:46 UTC

Updated at

2022-09-09 22:46:46 UTC

NP-MRD ID

NP0291618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gymnemic acid iii

Description

Gymnemic acid III, also known as gymnemate III, 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. gymnemic acid iii is found in Gymnema sylvestre. gymnemic acid iii was first documented in 2015 (PMID: 26058590). Based on a literature review very few articles have been published on Gymnemic acid III.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200462D          

 54 59  0  0  1  0            999 V2000
   -3.4105   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -3.8230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5855   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105   -5.9664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -6.4514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -3.8230    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -2.3941    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3145   -1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -0.9651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -2.3941    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9645   -1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -3.1086    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.7895   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -3.8230    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9645   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9337   -6.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955   -6.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6882   -6.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732   -2.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977   -3.3858    0.0000 C   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  1  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 31 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  6  0  0  0
 37 39  1  0  0  0  0
 29 39  1  0  0  0  0
 39 40  1  1  0  0  0
 27 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  1  0  0  0
 43 44  1  0  0  0  0
 41 45  1  0  0  0  0
 23 45  1  0  0  0  0
 45 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 22 48  1  0  0  0  0
 17 48  1  0  0  0  0
 48 49  1  6  0  0  0
 50 19  1  1  0  0  0
 11 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
  8 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  1  0  0  0  0
M  END

     RDKit          3D

120125  0  0  0  0  0  0  0  0999 V2000
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   -6.9617    0.2980    0.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6066    0.3843    0.6916 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8594   -0.8816    0.6320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0175   -0.9527    1.7469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873   -1.0959   -0.6153 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1028   -1.5903   -1.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1094   -0.7297   -1.9432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1834   -2.3105   -0.4521 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7348   -3.4508   -1.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8235   -2.1639   -1.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1256   -1.0019   -0.4659 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9066   -1.2465    1.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9330    0.2211   -0.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2799    1.3566   -0.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1506    1.5971   -0.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942    0.3205   -0.2649 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.2070   -2.0892   -0.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9050   -2.7598   -2.1018 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0787   -0.8474   -0.6664 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4288   -1.7247   -1.6711 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9806   -1.9780   -1.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2390   -0.7072   -1.1285 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0146   -0.2171   -2.5391 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4338    1.2118   -0.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0444    1.1202   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0178   -2.6944   -0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5579   -2.7738   -2.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5279   -1.4309   -2.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0291618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)O[C@H]1[C@H](O)[C@]2(CO)[C@@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)C(O)=O)[C@@](C)(CO)[C@@H]5CC[C@@]34C)[C@@H]2CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C41H66O13/c1-9-20(2)34(51)54-32-31(48)41(19-43)22(16-36(32,3)4)21-10-11-24-37(5)14-13-26(52-35-29(47)27(45)28(46)30(53-35)33(49)50)38(6,18-42)23(37)12-15-39(24,7)40(21,8)17-25(41)44/h10,20,22-32,35,42-48H,9,11-19H2,1-8H3,(H,49,50)/t20-,22-,23+,24+,25-,26-,27-,28-,29+,30-,31-,32-,35+,37-,38-,39+,40+,41-/m0/s1

> <INCHI_KEY>
VLXWTKUXVXJELF-DDRSIQBQSA-N

> <FORMULA>
C41H66O13

> <MOLECULAR_WEIGHT>
766.966

> <EXACT_MASS>
766.450342185

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
120

> <JCHEM_AVERAGE_POLARIZABILITY>
84.98743049284859

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(3S,4R,4aR,6aR,6bS,8S,8aR,9R,10R,12aS,14aR,14bR)-8,9-dihydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2S)-2-methylbutanoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_LOGP>
2.139635332999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.204255871628908

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5182148378039213

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8299735296489894

> <JCHEM_POLAR_SURFACE_AREA>
223.66999999999996

> <JCHEM_REFRACTIVITY>
194.92980000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(3S,4R,4aR,6aR,6bS,8S,8aR,9R,10R,12aS,14aR,14bR)-8,9-dihydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2S)-2-methylbutanoyl]oxy}-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.366  -5.803   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.826  -5.803   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.056  -7.136   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.826  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.516  -7.136   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.746  -5.803   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.088 -12.043   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.424  -7.136   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.654  -5.803   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.424  -4.469   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.654  -3.135   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.114  -3.135   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      14.424  -1.802   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      15.964  -4.469   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      16.734  -3.135   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      16.734  -5.803   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      18.274  -5.803   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      15.964  -7.136   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      16.734  -8.470   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      13.058 -11.847   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       6.885 -11.335   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       0.510  -5.597   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -0.742  -6.320   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   52                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14   50                                             
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19   48                                             
CONECT   18   17                                                            
CONECT   19   17   20   50                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   48                                                  
CONECT   23   22   24   25   45                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   41                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   39                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   31   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   29   40                                                  
CONECT   40   39                                                            
CONECT   41   27   42   43   45                                             
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43                                                            
CONECT   45   41   23   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   22   17   49                                             
CONECT   49   48                                                            
CONECT   50   19   11   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51    8   53   54                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  118    0
END

View in JSmol

Synonyms

Value	Source
Gymnemate III	Generator

Chemical Formula

C₄₁H₆₆O₁₃

Average Mass

766.9660 Da

Monoisotopic Mass

766.45034 Da

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(3S,4R,4aR,6aR,6bS,8S,8aR,9R,10R,12aS,14aR,14bR)-8,9-dihydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2S)-2-methylbutanoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-6-{[(3S,4R,4aR,6aR,6bS,8S,8aR,9R,10R,12aS,14aR,14bR)-8,9-dihydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2S)-2-methylbutanoyl]oxy}-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)O[C@H]1[C@H](O)[C@]2(CO)[C@@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O)C(O)=O)[C@@](C)(CO)[C@@H]5CC[C@@]34C)[C@@H]2CC1(C)C

InChI Identifier

InChI=1S/C41H66O13/c1-9-20(2)34(51)54-32-31(48)41(19-43)22(16-36(32,3)4)21-10-11-24-37(5)14-13-26(52-35-29(47)27(45)28(46)30(53-35)33(49)50)38(6,18-42)23(37)12-15-39(24,7)40(21,8)17-25(41)44/h10,20,22-32,35,42-48H,9,11-19H2,1-8H3,(H,49,50)/t20-,22-,23+,24+,25-,26-,27-,28-,29+,30-,31-,32-,35+,37-,38-,39+,40+,41-/m0/s1

InChI Key

VLXWTKUXVXJELF-DDRSIQBQSA-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
Gymnema sylvestre	LOTUS Database	35616633

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
Steroid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Beta-hydroxy acid
Fatty acid ester
Fatty acyl
Pyran
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Hydroxy acid
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Polyol
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
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	2.14	ChemAxon
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	223.67 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	194.93 m³·mol⁻¹	ChemAxon
Polarizability	84.99 Å³	ChemAxon
Number of Rings	6	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

HMDB0341055

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10259159

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14264066

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tiwari P, Sharma P, Khan F, Sangwan NS, Mishra BN, Sangwan RS: Structure Activity Relationship Studies of Gymnemic Acid Analogues for Antidiabetic Activity Targeting PPARgamma. Curr Comput Aided Drug Des. 2015;11(1):57-71. doi: 10.2174/1573409911666150610093611. [PubMed:26058590 ]
LOTUS database [Link]

Showing NP-Card for gymnemic acid iii (NP0291618)

MOL for NP0291618 (gymnemic acid iii)

3D MOL for NP0291618 (gymnemic acid iii)

3D SDF for NP0291618 (gymnemic acid iii)

3D-SDF for NP0291618 (gymnemic acid iii)

PDB for NP0291618 (gymnemic acid iii)

3D PDB for NP0291618 (gymnemic acid iii)

SMILES for NP0291618 (gymnemic acid iii)

INCHI for NP0291618 (gymnemic acid iii)

Structure for NP0291618 (gymnemic acid iii)

3D Structure for NP0291618 (gymnemic acid iii)