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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2022-07-12 20:54:12 UTC

Update Date

2022-07-12 20:54:13 UTC

HMDB ID

HMDB0341054

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Gymnemic acid II

Description

Gymnemic acid II, also known as gymnemate II, 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 very few articles have been published on Gymnemic acid II.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307122223252D          

 57 62  0  0  1  0            999 V2000
   -7.6974   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8724   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4599   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9849   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1599   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7474   -3.4914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9224   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9224   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6849   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5526   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9651   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7901   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4898   -3.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5474   -3.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0276   -0.6336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4401    0.0809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2651    0.0809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6776   -0.6336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2651   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6776    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1599   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136   -0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6845   -0.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961   -3.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8099   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -4.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7385   -3.1125    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  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  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 25 30  1  6  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 35 37  1  1  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 34 40  1  6  0  0  0
 33 41  1  1  0  0  0
 32 42  1  6  0  0  0
 22 43  1  6  0  0  0
 18 44  1  6  0  0  0
 45 14  1  1  0  0  0
 10 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
  8 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 13 50  1  1  0  0  0
 11 51  1  6  0  0  0
 10 52  1  6  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
  9 57  1  1  0  0  0
M  END


  Mrv1652307122223252D          

 57 62  0  0  1  0            999 V2000
   -7.6974   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8724   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4599   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9849   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1599   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7474   -3.4914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9224   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9224   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6849   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5526   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5526   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9651   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7901   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4898   -3.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -3.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5474   -3.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   -1.3480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0276   -0.6336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4401    0.0809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2651    0.0809    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6776   -0.6336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2651   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5026   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9151   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6776    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1599   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136   -0.5235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6845   -0.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961   -3.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1599   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8099   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3974   -4.9204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349   -4.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7385   -3.1125    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  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  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 25 30  1  6  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 35 37  1  1  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 34 40  1  6  0  0  0
 33 41  1  1  0  0  0
 32 42  1  6  0  0  0
 22 43  1  6  0  0  0
 18 44  1  6  0  0  0
 45 14  1  1  0  0  0
 10 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
  8 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 13 50  1  1  0  0  0
 11 51  1  6  0  0  0
 10 52  1  6  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  2  0  0  0  0
 54 56  1  0  0  0  0
  9 57  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0341054

> <DATABASE_NAME>
hmdb

> <SMILES>
CC[C@H](C)C(=O)O[C@H]1[C@H](O)[C@]2(COC(C)=O)[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/C43H68O14/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/h11,21,24-34,37,44,46-50H,10,12-20H2,1-9H3,(H,51,52)/t21-,24-,25+,26+,27-,28-,29-,30-,31+,32-,33-,34-,37+,39-,40-,41+,42+,43-/m0/s1

> <INCHI_KEY>
IWLKKMZNFBKYCF-GAZXINLWSA-N

> <FORMULA>
C43H68O14

> <MOLECULAR_WEIGHT>
809.003

> <EXACT_MASS>
808.46090687

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
125

> <JCHEM_AVERAGE_POLARIZABILITY>
89.24136310697862

> <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-{[(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

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
2.5807607433333306

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.204347201353709

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5182148378041096

> <JCHEM_PKA_STRONGEST_BASIC>
-2.785723760002405

> <JCHEM_POLAR_SURFACE_AREA>
229.73999999999995

> <JCHEM_REFRACTIVITY>
204.08130000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.85e-02 g/l

> <JCHEM_TRADITIONAL_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-{[(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                                 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     -14.368  -1.183   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.828  -1.183   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.058  -2.516   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.828  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.518  -2.516   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -9.748  -1.183   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -9.748  -3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.208  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.438  -5.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.898  -5.184   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.128  -6.517   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.588  -6.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.818  -5.184   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.588  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.818  -2.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.278  -2.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.508  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.278  -5.184   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.508  -6.517   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.032  -6.517   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.802  -5.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.032  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.802  -2.516   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.342  -2.516   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.112  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.342  -5.184   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.648  -6.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.395  -6.723   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.755  -7.446   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.652  -3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.422  -2.516   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.652  -1.183   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.422   0.151   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.962   0.151   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.732  -1.183   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.962  -2.516   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.272  -1.183   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.042   0.151   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      11.042  -2.516   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       8.732   1.485   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       5.652   1.485   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       4.112  -1.183   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.262  -2.516   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.048  -6.517   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -5.128  -3.850   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -5.898  -2.516   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -7.438  -2.516   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -7.492  -0.977   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -8.744  -1.700   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -2.979  -6.715   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -5.898  -7.851   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -6.668  -6.517   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -8.208  -6.517   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -8.978  -7.851   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -8.208  -9.185   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0     -10.518  -7.851   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      -8.845  -5.810   0.000  0.00  0.00           O+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   47                                                  
CONECT    9    8   10   57                                                  
CONECT   10    9   11   45   52                                             
CONECT   11   10   12   51                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18   50                                             
CONECT   14   13   15   45                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   13   19   44                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   17   23   43                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   21   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33   42                                                  
CONECT   33   32   34   41                                                  
CONECT   34   33   35   40                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35   31                                                       
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   34                                                            
CONECT   41   33                                                            
CONECT   42   32                                                            
CONECT   43   22                                                            
CONECT   44   18                                                            
CONECT   45   14   10   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46    8   48   49                                             
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   13                                                            
CONECT   51   11                                                            
CONECT   52   10   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54                                                            
CONECT   57    9                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Gymnemate II	Generator

Chemical Formula

C₄₃H₆₈O₁₄

Average Molecular Weight

809.003

Monoisotopic Molecular Weight

808.46090687

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-{[(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)-8a-[(acetyloxy)methyl]-8,9-dihydroxy-4-(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

122144-48-3

SMILES

CC[C@H](C)C(=O)O[C@H]1[C@H](O)[C@]2(COC(C)=O)[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/C43H68O14/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/h11,21,24-34,37,44,46-50H,10,12-20H2,1-9H3,(H,51,52)/t21-,24-,25+,26+,27-,28-,29-,30-,31+,32-,33-,34-,37+,39-,40-,41+,42+,43-/m0/s1

InChI Key

IWLKKMZNFBKYCF-GAZXINLWSA-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
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Acetal
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	3.33	ALOGPS
logP	2.58	ChemAxon
logS	-4.6	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	11	ChemAxon
Refractivity	204.08 m³·mol⁻¹	ChemAxon
Polarizability	89.24 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

Not Available

Chemspider ID

34989686

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91617872

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Gymnemic acid II (HMDB0341054)

MOL for HMDB0341054 (Gymnemic acid II)

3D MOL for HMDB0341054 (Gymnemic acid II)

3D SDF for HMDB0341054 (Gymnemic acid II)

3D-SDF for HMDB0341054 (Gymnemic acid II)

PDB for HMDB0341054 (Gymnemic acid II)

3D PDB for HMDB0341054 (Gymnemic acid II)

SMILES for HMDB0341054 (Gymnemic acid II)

INCHI for HMDB0341054 (Gymnemic acid II)

Structure for HMDB0341054 (Gymnemic acid II)

3D Structure for HMDB0341054 (Gymnemic acid II)

Predicted Kovats Retention Indices