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COCONUT Compound

Ajugachin A

CNP0282833.3 · C28H40O10 · View on COCONUT ↗

2D Structure

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Identifiers

NameAjugachin A
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-methylpropanoate
COCONUT IDCNP0282833.3
InChIKeyMZEYOXXDMOFRMK-QOAKXUCVSA-N
InChIInChI=1S/C28H40O10/c1-14(2)24(32)38-23-19(31)11-20-26(6,21-10-18-7-8-33-25(18)37-21)15(3)9-22(36-17(5)30)27(20,12-34-16(4)29)28(23)13-35-28/h7-8,14-15,18-23,25,31H,9-13H2,1-6H3/t15-,18-,19-,20-,21+,22+,23+,25+,26+,27+,28-/m1/s1
SMILESCC(=O)OC[C@@]12[C@@H](OC(C)=O)C[C@@H](C)[C@](C)([C@@H]3C[C@H]4C=CO[C@H]4O3)[C@H]1C[C@@H](O)[C@H](OC(=O)C(C)C)[C@]21CO1

Properties

Molecular FormulaC28H40O10
Molecular Weight536.62
Exact Mass536.26215
Log P (ALogP)2.51
TPSA130.12
H-Bond Donors / Acceptors1 / 10
Rotatable Bonds6
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.31
NP-likeness3.34

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 (3)

  1. 10.1016/0031-9422(90)87108-7
  2. 10.1016/S0031-9422(00)84101-1
  3. 10.1016/S0031-9422(98)00445-2

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.