Structure Database (LMSD)

Common Name
Gymnemic acid I
Systematic Name
(3β,4α,16β,21β,22α)-21-tigloxy-28-acetoxy-16,22,23-trihydroxyolean-12-en-3-yl-β D-glucopyranosiduronic acid
Synonyms
LM ID
LMPR0106150031
Formula
C43H66O14
Exact Mass
Calculate m/z
806.445261
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C30 isoprenoids (triterpenes) [PR0106]
Oleanane triterpenoids [PR010615]

Biological Context

Gymnemic acid I is a triterpene glycoside that has been found in G. sylvestre and has antihyperglycemic activities.1,2 It inhibits glucose-induced phosphorylation of serine 70 on S6 kinase (S6K1) and serine 2448 on mTOR, caspase-3 activity, and apoptosis, as well as increases autophagy in MIN-6 pancreatic β cells when used at a concentration of 5 µg/ml.1 Gymnemic acid I has been used as a reference compound to compare the potency of plant-derived sweet taste inhibitors.2

This information has been provided by Cayman Chemical

References

1. Kinghorn, A.D., Chin, Y.-W., Pan, L., et al. Natural Products as Sweeteners and Sweetness Modifiers. Comprehensive Natural Products II 269-315 (2010).
2. Wu, Y., Hu, Y., Yuan, Y., et al. Gymnemic acid I triggers mechanistic target of rapamycin-mediated β cells cytoprotection through the promotion of autophagy under high glucose stress. J. Cell. Physiol. 234(6), 9370-9377 (2019).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Gymnema sylvestre (#4068)
Magnoliopsida (#3398)
Isolation and structure elucidation of gymnemic acids, antisweet principles of Gymnema sylvestre.,
Chem Pharm Bull (Tokyo), 1992
Pubmed ID: 1327559
Gymnema sylvestre (#4068)
Magnoliopsida (#3398)
Isolation and structure elucidation of gymnemic acids, antisweet principles of Gymnema sylvestre.,
Chem Pharm Bull (Tokyo), 1992
Pubmed ID: 1327559

String Representations

InChiKey (Click to copy)
VEFSVJGWJQPWFS-ZXKKMYOJSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1C[C@]2(C)[C@@]3([H])CC=C4[C@]5([H])CC(C)(C)[C@@H](OC(/C(/C)=C/C)=O)[C@H](O)[C@]5(COC(C)=O)[C@@H](O)C[C@@]4(C)[C@]3(C)CC[C@@]2([H])[C@@](CO)(C)[C@H]1O[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O

Other Databases

KEGG ID
C08947
CHEBI ID
5577
PubChem CID
11953919
Cayman ID
28495

Calculated Physicochemical Properties

Heavy Atoms 57
Rings 6
Aromatic Rings 0
Rotatable Bonds 10
Van der Waals Molecular Volume 788.16
Topological Polar Surface Area 231.81
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 14
logP 6.18
Molar Refractivity 209.34

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Created at
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Updated at
13th Mar 2025