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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2022-07-12 20:56:03 UTC

Update Date

2022-07-12 20:56:03 UTC

HMDB ID

HMDB0341056

Secondary Accession Numbers

None

Metabolite 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. Based on a literature review a small amount of articles have been published on Gymnemic acid I.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307122223272D          

 70 75  0  0  1  0            999 V2000
   -1.9816    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9557   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8742   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3627    1.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1197    1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5059   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6809   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4434    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2812    1.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7441    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6809    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4434    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9684    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9184    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1559   -1.7309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    8.7434   -1.0164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3934   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7309    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3184    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2184   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1559   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5059    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0309    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2059    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5559    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4244    2.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7434   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3934   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9184   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6309   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6309   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4934    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6184    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3309    1.1270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684   -2.4454    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059   -1.7309    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309   -0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684   -1.0164    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059    1.1270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 12 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 21  2  1  0  0  0  0
 21 10  2  0  0  0  0
 22  3  1  0  0  0  0
 23 11  2  0  0  0  0
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 38 34  1  0  0  0  0
 39  6  1  1  0  0  0
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 40  7  1  1  0  0  0
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 41  8  1  1  0  0  0
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 43 27  1  0  0  0  0
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 44 19  1  0  0  0  0
 45 22  2  0  0  0  0
 27 46  1  1  0  0  0
 29 47  1  6  0  0  0
 30 48  1  1  0  0  0
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 33 50  1  1  0  0  0
 51 35  2  0  0  0  0
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 53 36  2  0  0  0  0
 54 20  1  0  0  0  0
 54 22  1  0  0  0  0
 28 55  1  1  0  0  0
 37 55  1  6  0  0  0
 56 32  1  0  0  0  0
 56 37  1  0  0  0  0
 34 57  1  1  0  0  0
 57 36  1  0  0  0  0
 58 10  1  0  0  0  0
 24 59  1  1  0  0  0
 25 60  1  6  0  0  0
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 29 64  1  1  0  0  0
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 31 66  1  6  0  0  0
 32 67  1  1  0  0  0
 33 68  1  1  0  0  0
 34 69  1  6  0  0  0
 37 70  1  1  0  0  0
M  END


  Mrv1652307122223272D          

 70 75  0  0  1  0            999 V2000
   -1.9816    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9557   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8742   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3627    1.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1197    1.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0309   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2684    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5059   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4434    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7934    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2812    1.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7441    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9809   -1.7309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   10.3934   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    8.3309   -0.3020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9059    1.1270    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
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 28 63  1  6  0  0  0
 29 64  1  1  0  0  0
 30 65  1  6  0  0  0
 31 66  1  6  0  0  0
 32 67  1  1  0  0  0
 33 68  1  1  0  0  0
 34 69  1  6  0  0  0
 37 70  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0341056

> <DATABASE_NAME>
hmdb

> <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

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
2.664481777333336

> <ALOGPS_LOGS>
-4.49

> <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

> <ALOGPS_SOLUBILITY>
2.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gymnemic acid I

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-JUL-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-JUL-22         0                                  
HETATM    1  C   UNK     0      -3.699   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.159   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.461   6.105   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.784  -1.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.498  -2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.931  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.744   3.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.690   3.635   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.159   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.851  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.391  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.701   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.011  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.471  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.161   3.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.771  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081   3.437   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.458   2.630   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   3.437   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.389   2.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   6.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.471   2.104   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.161   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.541   3.437   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.781   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.091  -3.231   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.631  -3.231   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.321  -1.897   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.401  -1.897   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.231   2.104   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.461   0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.941  -1.897   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.151   2.104   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      17.091  -0.564   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.701   0.770   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.011   2.104   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.391   2.104   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.851   2.104   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.771   2.104   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      15.726   4.147   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       4.771   7.438   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       5.702   4.969   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      16.321  -4.565   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      19.401  -4.565   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      14.781  -1.897   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       2.461   3.437   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      21.711  -0.564   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      21.711  -3.231   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       0.921   3.437   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       4.771   4.771   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      16.321   0.770   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      18.631  -0.564   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       0.921   0.770   0.000  0.00  0.00           O+0
HETATM   58  H   UNK     0      -1.389   4.771   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0       6.311   2.104   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0      13.241   0.770   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0       8.621   0.770   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0       6.685   4.468   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0      15.551   2.104   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0      17.861  -4.565   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0      20.171  -3.231   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0      15.551  -0.564   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0      17.861  -1.897   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.691   2.104   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0      17.861   0.770   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4   38                                                            
CONECT    5   38                                                            
CONECT    6   39                                                            
CONECT    7   40                                                            
CONECT    8   41                                                            
CONECT    9   42                                                            
CONECT   10    1   21   58                                                  
CONECT   11   12   23                                                       
CONECT   12   11   26                                                       
CONECT   13   16   25                                                       
CONECT   14   15   28                                                       
CONECT   15   14   39                                                       
CONECT   16   13   41                                                       
CONECT   17   24   38                                                       
CONECT   18   27   42                                                       
CONECT   19   40   44                                                       
CONECT   20   43   54                                                       
CONECT   21    2   10   36                                                  
CONECT   22    3   45   54                                                  
CONECT   23   11   24   42                                                  
CONECT   24   17   23   43   59                                             
CONECT   25   13   39   40   60                                             
CONECT   26   12   39   41   61                                             
CONECT   27   18   43   46   62                                             
CONECT   28   14   40   55   63                                             
CONECT   29   30   31   47   64                                             
CONECT   30   29   32   48   65                                             
CONECT   31   29   37   49   66                                             
CONECT   32   30   35   56   67                                             
CONECT   33   34   43   50   68                                             
CONECT   34   33   38   57   69                                             
CONECT   35   32   51   52                                                  
CONECT   36   21   53   57                                                  
CONECT   37   31   55   56   70                                             
CONECT   38    4    5   17   34                                             
CONECT   39    6   15   25   26                                             
CONECT   40    7   19   25   28                                             
CONECT   41    8   16   26   42                                             
CONECT   42    9   18   23   41                                             
CONECT   43   20   24   27   33                                             
CONECT   44   19                                                            
CONECT   45   22                                                            
CONECT   46   27                                                            
CONECT   47   29                                                            
CONECT   48   30                                                            
CONECT   49   31                                                            
CONECT   50   33                                                            
CONECT   51   35                                                            
CONECT   52   35                                                            
CONECT   53   36                                                            
CONECT   54   20   22                                                       
CONECT   55   28   37                                                       
CONECT   56   32   37                                                       
CONECT   57   34   36                                                       
CONECT   58   10                                                            
CONECT   59   24                                                            
CONECT   60   25                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   29                                                            
CONECT   65   30                                                            
CONECT   66   31                                                            
CONECT   67   32                                                            
CONECT   68   33                                                            
CONECT   69   34                                                            
CONECT   70   37                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  150    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Gymnemate I	Generator

Chemical Formula

C₄₃H₆₆O₁₄

Average Molecular Weight

806.987

Monoisotopic Molecular Weight

806.445256805

IUPAC Name

(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

Traditional Name

gymnemic acid I

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

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 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.43	ALOGPS
logP	2.66	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.52	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	229.74 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	204.96 m³·mol⁻¹	ChemAxon
Polarizability	88.27 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

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1667731

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Gymnemic acid I (HMDB0341056)

MOL for HMDB0341056 (Gymnemic acid I)

3D MOL for HMDB0341056 (Gymnemic acid I)

3D SDF for HMDB0341056 (Gymnemic acid I)

3D-SDF for HMDB0341056 (Gymnemic acid I)

PDB for HMDB0341056 (Gymnemic acid I)

3D PDB for HMDB0341056 (Gymnemic acid I)

SMILES for HMDB0341056 (Gymnemic acid I)

INCHI for HMDB0341056 (Gymnemic acid I)

Structure for HMDB0341056 (Gymnemic acid I)

3D Structure for HMDB0341056 (Gymnemic acid I)

Predicted Kovats Retention Indices