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COCONUT Compound

AJUGAPITIN

CNP0140378.1 · C29H42O10 · View on COCONUT ↗

2D Structure

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Identifiers

NameAJUGAPITIN
IUPAC Name[(1~{R},2~{S},3~{R},4~{a}~{R},5~{S},6~{R},8~{S},8~{a}~{R})-5-[(3~{a}~{S},5~{S},6~{a}~{S})-3~{a},4,5,6~{a}-tetrahydrofuro[2,3-b]furan-5-yl]-8-acetoxy-8~{a}-(acetoxymethyl)-3-hydroxy-5,6-dimethyl-spiro[decalin-1,2'-oxirane]-2-yl] 2-methylbutanoate
COCONUT IDCNP0140378.1
InChIKeyLHFSTOLZQVESJD-DBNYLVSFSA-N
InChIInChI=1S/C29H42O10/c1-7-15(2)25(33)39-24-20(32)12-21-27(6,22-11-19-8-9-34-26(19)38-22)16(3)10-23(37-18(5)31)28(21,13-35-17(4)30)29(24)14-36-29/h8-9,15-16,19-24,26,32H,7,10-14H2,1-6H3/t15?,16-,19-,20-,21-,22+,23+,24+,26+,27+,28+,29-/m1/s1
SMILESCCC(C)C(=O)O[C@H]1[C@H](O)C[C@@H]2[C@@](C)([C@@H]3C[C@H]4C=CO[C@H]4O3)[C@H](C)C[C@H](OC(C)=O)[C@@]2(COC(C)=O)[C@@]12CO2

Properties

Molecular FormulaC29H42O10
Molecular Weight550.65
Exact Mass550.27780
Log P (ALogP)2.90
TPSA130.12
H-Bond Donors / Acceptors1 / 10
Rotatable Bonds7
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.29
NP-likeness3.32

Classification

NP PathwayTerpenoids
NP SuperclassDiterpenoids
NP ClassColensane and Clerodane diterpenoids
Chemical SuperclassOrganic acids and derivatives
Chemical ClassCarboxylic acids and derivatives
Chemical SubclassTricarboxylic acids and derivatives

Reported in GR-MAPs Plants

Ajuga chamaepitys as “Ajuga chamaepitys” in COCONUT

References (2)

  1. 10.1016/S0031-9422(00)84101-1
  2. 10.1016/S0031-9422(96)00850-3

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.