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COCONUT Compound

(2R,3R,4S,5S,6R)-2-{[(4aS,5S,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-9-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicen-4a-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CNP0200173.1 · C42H70O14 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

Name(2R,3R,4S,5S,6R)-2-{[(4aS,5S,6aS,6bR,8aR,9R,10S,12aR,12bR,14bS)-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-9-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicen-4a-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
IUPAC Name(2~{R},3~{R},4~{S},5~{S},6~{R})-2-[[(3~{S},4~{R},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{S},8~{a}~{S},12~{a}~{S},14~{a}~{R},14~{b}~{R})-3,8-dihydroxy-4,6~{a},6~{b},11,11,14~{b}-hexamethyl-8~{a}-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]-1,2,3,4~{a},5,6,7,8,9,10,12,12~{a},14,14~{a}-tetradecahydropicen-4-yl]methoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
COCONUT IDCNP0200173.1
InChIKeyMPYXSUXOGIBNAU-DZRQGSMDSA-N
InChIInChI=1S/C42H70O14/c1-37(2)13-14-42(20-54-36-34(52)32(50)30(48)24(18-44)56-36)22(15-37)21-7-8-26-38(3)11-10-27(45)39(4,19-53-35-33(51)31(49)29(47)23(17-43)55-35)25(38)9-12-40(26,5)41(21,6)16-28(42)46/h7,22-36,43-52H,8-20H2,1-6H3/t22-,23+,24+,25+,26+,27-,28-,29+,30+,31-,32-,33+,34+,35+,36+,38-,39-,40+,41+,42+/m0/s1
SMILESCC1(C)CC[C@]2(CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(CO[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@H]5CC[C@]43C)[C@@H]2C1

Properties

Molecular FormulaC42H70O14
Molecular Weight799.01
Exact Mass798.47656
Log P (ALogP)0.73
TPSA239.22
H-Bond Donors / Acceptors10 / 14
Rotatable Bonds8
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.15
NP-likeness2.36

Classification

NP PathwayTerpenoids
NP SuperclassTriterpenoids
NP ClassOleanane triterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassTerpene glycosides

Reported in GR-MAPs Plants

Gymnema sylvester as “Gymnema sylvestre” in COCONUT

References (4)

  1. 10.1016/S0040-4039(00)74887-8
  2. 10.1016/s0040-4039(00)74887-8
  3. 10.1248/CPB.44.469
  4. 10.1248/CPB.45.1671

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.