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COCONUT Compound

Sigmoidin B

CNP0229475.2 · C20H20O6 · View on COCONUT ↗

2D Structure

Download 2D SDF Download 3D SDF

Identifiers

NameSigmoidin B
IUPAC Name(2~{S})-2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-chroman-4-one
COCONUT IDCNP0229475.2
CAS87746-47-2
InChIKeySFQIGPZCFNTPOD-KRWDZBQOSA-N
InChIInChI=1S/C20H20O6/c1-10(2)3-4-11-5-12(6-16(24)20(11)25)17-9-15(23)19-14(22)7-13(21)8-18(19)26-17/h3,5-8,17,21-22,24-25H,4,9H2,1-2H3/t17-/m0/s1
SMILESCC(C)=CCC1=CC([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)=CC(O)=C1O

Properties

Molecular FormulaC20H20O6
Molecular Weight356.37
Exact Mass356.12599
Log P (ALogP)3.72
TPSA107.22
H-Bond Donors / Acceptors4 / 6
Rotatable Bonds3
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.49
NP-likeness2.36

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassIsoflavonoids
NP ClassFlavanones
Chemical SuperclassPhenylpropanoids and polyketides
Chemical ClassFlavonoids
Chemical SubclassFlavans

Reported in GR-MAPs Plants

Glycyrrhiza glabra as “Glycyrrhiza glabra” in COCONUT

References (14)

  1. 10.1016/0031-9422(86)88044-X
  2. 10.1016/S0031-9422(00)95111-2
  3. 10.1016/S0040-4039(00)88279-9
  4. 10.1016/S0367-326X(00)00142-8
  5. 10.1021/NP060477+
  6. 10.1021/NP960440X
  7. 10.1021/np060477+
  8. 10.1021/np960440x
  9. 10.1039/P19860000033
  10. 10.1055/S-2004-815484
  11. 10.1055/S-2006-962368
  12. 10.1055/s-2004-815484
  13. 10.1248/YAKUSHI.123.619
  14. 10.3987/COM-89-4998

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.