NP-MRD: Showing NP-Card for Gymnemic acid I (NP0138015)

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Record Information

Version

2.0

Created at

2022-05-31 16:43:14 UTC

Updated at

2022-05-31 16:43:14 UTC

NP-MRD ID

NP0138015

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gymnemic acid I

Description

Gymnemic acid i, also known as gymnemate I, 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 I is found in Gymnema sylvestre. Gymnemic acid I was first documented in 2015 (PMID: 26058590). Based on a literature review a small amount of articles have been published on Gymnemic acid i (PMID: 34917786) (PMID: 30370588) (PMID: 28256837).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218432D          

 70 75  0  0  1  0            999 V2000
   -2.1730   -6.6809    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -5.2520    0.0000 C   0  0  0  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   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -5.9664    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
   -0.5230   -3.8230    0.0000 H   0  0  0  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
   -0.5230   -5.2520    0.0000 H   0  0  0  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
    1.1270   -6.6809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -7.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -8.1099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -7.3954    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
    1.9520   -5.2520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -6.7869    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
    4.4270   -5.2520    0.0000 H   0  0  0  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
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    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    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
    8.1395   -4.5375    0.0000 H   0  0  0  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
    8.1395   -1.6796    0.0000 H   0  0  0  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
    9.3770   -2.3941    0.0000 H   0  0  0  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
    9.3770   -3.8230    0.0000 H   0  0  0  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
    8.1395   -3.1086    0.0000 H   0  0  0  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
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    5.2520   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    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
    1.9520   -3.8230    0.0000 H   0  0  0  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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  1  0  0  0
 11 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  1  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  6  0  0  0
 38 37  1  6  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  6  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  6  0  0  0
 46 48  1  1  0  0  0
 46 49  1  0  0  0  0
 49 50  1  1  0  0  0
 49 51  1  6  0  0  0
 49 52  1  0  0  0  0
 38 52  1  0  0  0  0
 52 53  1  6  0  0  0
 52 54  1  6  0  0  0
 35 55  1  0  0  0  0
 55 56  1  6  0  0  0
 55 57  1  1  0  0  0
 57 58  1  0  0  0  0
 55 59  1  0  0  0  0
 31 59  1  0  0  0  0
 59 60  1  1  0  0  0
 59 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 24 63  1  0  0  0  0
 29 63  1  0  0  0  0
 63 64  1  6  0  0  0
 26 65  1  0  0  0  0
 14 65  1  0  0  0  0
 65 66  1  6  0  0  0
 65 67  1  0  0  0  0
 67 68  1  0  0  0  0
  9 68  1  0  0  0  0
 68 69  1  0  0  0  0
 68 70  1  0  0  0  0
M  END

     RDKit          3D

123128  0  0  0  0  0  0  0  0999 V2000
   11.1823   -1.7488   -1.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7531   -1.5352   -1.5360 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5896   -0.8067   -0.8094 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3654    0.2527    0.2174 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8042   -0.3064    1.4462 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9847    0.7292    0.4090 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0761    2.2392    0.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6528    0.7012   -0.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918    1.2310   -1.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5704    1.4905   -1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0652    0.5672   -0.1787 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5439    0.4818   -0.1217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2899    1.7287   -0.4810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9187   -0.5427   -1.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6156    2.5744   -0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824   -0.4438   -0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
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 57123  1  0
M  END


  Mrv1652305312218432D          

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  9 68  1  0  0  0  0
 68 69  1  0  0  0  0
 68 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138015

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C43H66O14/c1-10-21(2)36(53)57-34-33(50)43(20-54-22(3)45)24(17-38(34,4)5)23-11-12-26-39(6)15-14-28(55-37-31(49)29(47)30(48)32(56-37)35(51)52)40(7,19-44)25(39)13-16-41(26,8)42(23,9)18-27(43)46/h10-11,24-34,37,44,46-50H,12-20H2,1-9H3,(H,51,52)/b21-10+/t24-,25+,26+,27-,28-,29-,30-,31+,32-,33-,34-,37+,39-,40-,41+,42+,43-/m0/s1

> <INCHI_KEY>
VEFSVJGWJQPWFS-ZXKKMYOJSA-N

> <FORMULA>
C43H66O14

> <MOLECULAR_WEIGHT>
806.987

> <EXACT_MASS>
806.445256805

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
88.27264899209686

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <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)-8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2E)-2-methylbut-2-enoyl]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>
2.664481777333336

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.204319728332118

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5182148378040545

> <JCHEM_PKA_STRONGEST_BASIC>
-2.785723760002405

> <JCHEM_POLAR_SURFACE_AREA>
229.73999999999998

> <JCHEM_REFRACTIVITY>
204.95720000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
gymnemic acid I

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0      -4.056 -12.471   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -4.826 -11.137   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.366 -11.137   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.056  -9.804   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.826  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.516  -9.804   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.746 -11.137   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.746  -8.470   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -0.976  -7.136   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      -0.976  -9.804   0.000  0.00  0.00           H+0
HETATM   13  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.104 -12.471   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334 -13.805   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.104 -15.138   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.206 -13.805   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       3.644  -9.804   0.000  0.00  0.00           H+0
HETATM   22  O   UNK     0       3.035 -12.669   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0       8.264  -9.804   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0      12.884  -9.804   0.000  0.00  0.00           H+0
HETATM   37  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      14.424  -7.136   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0      15.194  -8.470   0.000  0.00  0.00           H+0
HETATM   40  O   UNK     0      13.654  -5.803   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      14.424  -4.469   0.000  0.00  0.00           C+0
HETATM   42  H   UNK     0      15.194  -3.135   0.000  0.00  0.00           H+0
HETATM   43  C   UNK     0      13.654  -3.135   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      12.114  -3.135   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      14.424  -1.802   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      15.964  -4.469   0.000  0.00  0.00           C+0
HETATM   47  H   UNK     0      17.504  -4.469   0.000  0.00  0.00           H+0
HETATM   48  O   UNK     0      16.734  -3.135   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      16.734  -5.803   0.000  0.00  0.00           C+0
HETATM   50  H   UNK     0      17.504  -7.136   0.000  0.00  0.00           H+0
HETATM   51  O   UNK     0      18.274  -5.803   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      15.964  -7.136   0.000  0.00  0.00           C+0
HETATM   53  H   UNK     0      15.194  -5.803   0.000  0.00  0.00           H+0
HETATM   54  O   UNK     0      16.734  -8.470   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      13.058 -11.847   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   60  H   UNK     0      10.574 -11.137   0.000  0.00  0.00           H+0
HETATM   61  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       6.885 -11.335   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   66  H   UNK     0       3.644  -7.136   0.000  0.00  0.00           H+0
HETATM   67  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0       0.510  -5.597   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      -0.742  -6.320   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   68                                             
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   20   65                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25   26   63                                             
CONECT   25   24                                                            
CONECT   26   24   27   65                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   63                                             
CONECT   30   29                                                            
CONECT   31   29   32   33   59                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37   55                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   40   52                                             
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42   43   46                                             
CONECT   42   41                                                            
CONECT   43   41   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   41   47   48   49                                             
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   46   50   51   52                                             
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   49   38   53   54                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   35   56   57   59                                             
CONECT   56   55                                                            
CONECT   57   55   58                                                       
CONECT   58   57                                                            
CONECT   59   55   31   60   61                                             
CONECT   60   59                                                            
CONECT   61   59   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   24   29   64                                             
CONECT   64   63                                                            
CONECT   65   26   14   66   67                                             
CONECT   66   65                                                            
CONECT   67   65   68                                                       
CONECT   68   67    9   69   70                                             
CONECT   69   68                                                            
CONECT   70   68                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  150    0
END

View in JSmol

Synonyms

Value	Source
Gymnemate I	Generator

Chemical Formula

C₄₃H₆₆O₁₄

Average Mass

806.9870 Da

Monoisotopic Mass

806.44526 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

122168-40-5

SMILES

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

InChI Identifier

InChI=1S/C43H66O14/c1-10-21(2)36(53)57-34-33(50)43(20-54-22(3)45)24(17-38(34,4)5)23-11-12-26-39(6)15-14-28(55-37-31(49)29(47)30(48)32(56-37)35(51)52)40(7,19-44)25(39)13-16-41(26,8)42(23,9)18-27(43)46/h10-11,24-34,37,44,46-50H,12-20H2,1-9H3,(H,51,52)/b21-10+/t24-,25+,26+,27-,28-,29-,30-,31+,32-,33-,34-,37+,39-,40-,41+,42+,43-/m0/s1

InChI Key

VEFSVJGWJQPWFS-ZXKKMYOJSA-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
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Pyran
Oxane
Fatty acyl
Monosaccharide
Hydroxy acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Carboxylic acid
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

triterpenoid saponin (CHEBI:5577 )
Dammarenes (C08947 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003523

Chemspider ID

10128218

KEGG Compound ID

C08947

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11953919

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1667731

References

General References

S Shenoy R, Kumar D J, Hg N, Manonmani HK: In silico evaluation of naturally isolated triterpene glycosides (TG) from Gymnema sylvestre towards diabetic treatment. Heliyon. 2021 Nov 16;7(12):e08407. doi: 10.1016/j.heliyon.2021.e08407. eCollection 2021 Dec. [PubMed:34917786 ]
Wu Y, Hu Y, Yuan Y, Luo Y, Lai D, Zhou H, Tong Z, Liu D: Gymnemic acid I triggers mechanistic target of rapamycin-mediated beta cells cytoprotection through the promotion of autophagy under high glucose stress. J Cell Physiol. 2019 Jun;234(6):9370-9377. doi: 10.1002/jcp.27621. Epub 2018 Oct 28. [PubMed:30370588 ]
Capolupo A, Esposito R, Zampella A, Festa C, Riccio R, Casapullo A, Tosco A, Monti MC: Determination of Gymnemic Acid I as a Protein Biosynthesis Inhibitor Using Chemical Proteomics. J Nat Prod. 2017 Apr 28;80(4):909-915. doi: 10.1021/acs.jnatprod.6b00793. Epub 2017 Mar 3. [PubMed:28256837 ]
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 ]

Showing NP-Card for Gymnemic acid I (NP0138015)

MOL for NP0138015 (Gymnemic acid I)

3D MOL for NP0138015 (Gymnemic acid I)

3D SDF for NP0138015 (Gymnemic acid I)

3D-SDF for NP0138015 (Gymnemic acid I)

PDB for NP0138015 (Gymnemic acid I)

3D PDB for NP0138015 (Gymnemic acid I)

SMILES for NP0138015 (Gymnemic acid I)

INCHI for NP0138015 (Gymnemic acid I)

Structure for NP0138015 (Gymnemic acid I)

3D Structure for NP0138015 (Gymnemic acid I)