COCONUT Compound

Gymnemic acid II

CNP0402022.2 · C43H68O14 · View on COCONUT ↗

Identifiers

NameGymnemic acid II
IUPAC Name(2~{S},3~{S},4~{S},5~{R},6~{R})-6-[[(3~{S},4~{R},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{S},8~{a}~{R},9~{R},10~{R},12~{a}~{S},14~{a}~{R},14~{b}~{R})-8~{a}-(acetoxymethyl)-8,9-dihydroxy-4-(hydroxymethyl)-4,6~{a},6~{b},11,11,14~{b}-hexamethyl-10-[(2~{S})-2-methylbutanoyl]oxy-1,2,3,4~{a},5,6,7,8,9,10,12,12~{a},14,14~{a}-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxy-tetrahydropyran-2-carboxylic acid
COCONUT IDCNP0402022.2
CAS122144-48-3
InChIKeyIWLKKMZNFBKYCF-GAZXINLWSA-N
InChIInChI=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
SMILESCC[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(=O)O)[C@@H](O)[C@H](O)[C@H]6O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]2CC1(C)C

Properties

Molecular FormulaC43H68O14
Molecular Weight809.00
Exact Mass808.46091
Log P (ALogP)3.11
TPSA229.74
H-Bond Donors / Acceptors7 / 13
Rotatable Bonds9
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.10
NP-likeness2.98

Classification

NP PathwayTerpenoids
NP SuperclassTriterpenoids
NP ClassOleanane triterpenoids
Chemical SuperclassOrganic oxygen compounds
Chemical ClassOrganooxygen compounds
Chemical SubclassCarbohydrates and carbohydrate conjugates

Reported in GR-MAPs Plants

Gymnema sylvester as “Gymnema sylvestre” in COCONUT

Data from COCONUT (COlleCtion of Open Natural prodUcTs), released under CC0. Chandrasekhar V. et al. COCONUT 2.0: a comprehensive overhaul and curation of the collection of open natural products database. Nucleic Acids Research (2024), doi:10.1093/nar/gkae1063. COCONUT release 2026-10.