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COCONUT Compound

(-)-Maackiain

CNP0366241.1 · C16H12O5 · View on COCONUT ↗

2D Structure

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Identifiers

Name(-)-Maackiain
IUPAC Name(1~{R},12~{R})-5,7,11,19-tetraoxapentacyclo[10.8.0.0^{2,10}.0^{4,8}.0^{13,18}]icosa-2,4(8),9,13,15,17-hexaen-16-ol
COCONUT IDCNP0366241.1
CAS2035-15-6, 19908-48-6
InChIKeyHUKSJTUUSUGIDC-ZBEGNZNMSA-N
InChIInChI=1S/C16H12O5/c17-8-1-2-9-12(3-8)18-6-11-10-4-14-15(20-7-19-14)5-13(10)21-16(9)11/h1-5,11,16-17H,6-7H2/t11-,16-/m0/s1
SMILESOC1=CC=C2C(=C1)OC[C@H]1C3=CC4=C(C=C3O[C@@H]21)OCO4

Properties

Molecular FormulaC16H12O5
Molecular Weight284.27
Exact Mass284.06847
Log P (ALogP)2.73
TPSA57.15
H-Bond Donors / Acceptors1 / 5
Rotatable Bonds0
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.81
NP-likeness2.06

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassIsoflavonoids
NP ClassPterocarpan
Chemical SuperclassPhenylpropanoids and polyketides
Chemical ClassIsoflavonoids
Chemical SubclassFuranoisoflavonoids

Reported in GR-MAPs Plants

Mucuna pruriens as “Mucuna Pruriens” in COCONUT
Tephrosia purpurea as “Tephrosia Purpurea” in COCONUT

References (90)

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  13. 10.1016/0031-9422(88)80277-2
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  18. 10.1016/0031-9422(92)90075-2
  19. 10.1016/0031-9422(93)85423-O
  20. 10.1016/0031-9422(94)00720-E
  21. 10.1016/0031-9422(94)00721-5
  22. 10.1016/0031-9422(95)91511-X
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  25. 10.1016/0305-1978(81)90030-2
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  33. 10.1016/S0031-9422(00)82217-7
  34. 10.1016/S0031-9422(00)89598-9
  35. 10.1016/S0031-9422(00)90868-9
  36. 10.1016/S0031-9422(00)97051-1
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  39. 10.1016/S0031-9422(01)00268-0
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Showing 40 of 90. See all references on COCONUT.

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.