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COCONUT Compound

(1~{R},6~{R},13~{R})-10,13-dihydroxy-6-isopropenyl-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one

CNP0248033.2 · C23H22O8 · View on COCONUT ↗

2D Structure

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Identifiers

IUPAC Name(1~{R},6~{R},13~{R})-10,13-dihydroxy-6-isopropenyl-16,17-dimethoxy-2,7,20-trioxapentacyclo[11.8.0.0^{3,11}.0^{4,8}.0^{14,19}]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
COCONUT IDCNP0248033.2
InChIKeyJCJPVNDLAAXNEX-WNHYQHMGSA-N
InChIInChI=1S/C23H22O8/c1-10(2)14-5-11-15(30-14)7-13(24)20-21(11)31-19-9-29-16-8-18(28-4)17(27-3)6-12(16)23(19,26)22(20)25/h6-8,14,19,24,26H,1,5,9H2,2-4H3/t14-,19-,23-/m1/s1
SMILESC=C(C)[C@H]1CC2=C(C=C(O)C3=C2O[C@@H]2COC4=CC(OC)=C(OC)C=C4[C@]2(O)C3=O)O1

Properties

Molecular FormulaC23H22O8
Molecular Weight426.42
Exact Mass426.13147
Log P (ALogP)2.51
TPSA103.68
H-Bond Donors / Acceptors2 / 8
Rotatable Bonds3
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.72
NP-likeness2.36

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassIsoflavonoids
NP ClassRotenoids
Chemical SuperclassPhenylpropanoids and polyketides
Chemical ClassIsoflavonoids
Chemical SubclassRotenoids

Reported in GR-MAPs Plants

Tephrosia purpurea as “Tephrosia purpurea” in COCONUT

References (4)

  1. 10.1002/(SICI)1521-4168(19980901)21:9<513::AID-JHRC513>3.0.CO,2-F
  2. 10.1016/S0031-9422(00)83209-4
  3. 10.1016/S0040-4039(01)83698-4
  4. 10.1080/14786419.2014.940587

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.