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COCONUT Compound

[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] (4~{a}~{S},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},10~{R},11~{R},12~{a}~{R},14~{b}~{S})-10,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6~{a},6~{b},12~{a}-pentamethyl-1,3,4,5,6,6~{a},7,8,8~{a},10,11,12,13,14~{b}-tetradecahydropicene-4~{a}-carboxylate

CNP0216560.1 · C36H58O11 · View on COCONUT ↗

2D Structure

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Identifiers

IUPAC Name[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl] (4~{a}~{S},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},10~{R},11~{R},12~{a}~{R},14~{b}~{S})-10,11-dihydroxy-9,9-bis(hydroxymethyl)-2,2,6~{a},6~{b},12~{a}-pentamethyl-1,3,4,5,6,6~{a},7,8,8~{a},10,11,12,13,14~{b}-tetradecahydropicene-4~{a}-carboxylate
COCONUT IDCNP0216560.1
InChIKeyWPWWZJOMLDEMLW-PFYJWDNZSA-N
InChIInChI=1S/C36H58O11/c1-31(2)10-12-35(30(45)47-29-27(43)26(42)25(41)22(16-37)46-29)13-11-33(4)19(20(35)14-31)6-7-23-32(3)15-21(40)28(44)36(17-38,18-39)24(32)8-9-34(23,33)5/h6,20-29,37-44H,7-18H2,1-5H3/t20-,21+,22+,23+,24+,25+,26-,27+,28-,29-,32+,33+,34+,35-/m0/s1
SMILESCC1(C)CC[C@]2(C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(CO)(CO)[C@@H]5CC[C@]43C)[C@@H]2C1

Properties

Molecular FormulaC36H58O11
Molecular Weight666.85
Exact Mass666.39791
Log P (ALogP)1.41
TPSA197.37
H-Bond Donors / Acceptors8 / 11
Rotatable Bonds5
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.16
NP-likeness3.01

Classification

NP PathwayTerpenoids
NP SuperclassTriterpenoids
NP ClassOleanane triterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassSteroids and steroid derivatives
Chemical SubclassHydroxysteroids

Reported in GR-MAPs Plants

Terminalia chebula as “Terminalia chebula” in COCONUT
Terminalia bellirica as “Terminalia bellirica” in COCONUT

References (6)

  1. 10.1016/0031-9422(93)85243-K
  2. 10.1016/0031-9422(93)85243-k
  3. 10.1016/J.PHYTOCHEM.2006.07.017
  4. 10.1016/S0031-9422(00)98085-3
  5. 10.1016/S0367-326X(01)00295-7
  6. 10.3390/MOLECULES13112717

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.