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COCONUT Compound

Rhein

CNP0221661.0 · C15H8O6 · View on COCONUT ↗

2D Structure

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Identifiers

NameRhein
IUPAC Name4,5-dihydroxy-9,10-dioxo-anthracene-2-carboxylic acid
COCONUT IDCNP0221661.0
CAS478-43-3
InChIKeyFCDLCPWAQCPTKC-UHFFFAOYSA-N
InChIInChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
SMILESO=C(O)C1=CC(O)=C2C(=O)C3=C(O)C=CC=C3C(=O)C2=C1

Properties

Molecular FormulaC15H8O6
Molecular Weight284.22
Exact Mass284.03209
Log P (ALogP)1.57
TPSA111.90
H-Bond Donors / Acceptors3 / 5
Rotatable Bonds1
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.62
NP-likeness1.06

Classification

NP PathwayPolyketides
NP SuperclassPolycyclic aromatic polyketides
NP ClassAnthraquinones and anthrones
Chemical SuperclassBenzenoids
Chemical ClassAnthracenes
Chemical SubclassAnthracenecarboxylic acids and derivatives

Reported in GR-MAPs Plants

Vitex negundo as “Vitex negundo” in COCONUT
Cassia angustifolia as “Cassia angustifolia; Senna alexandrina; Senna alexandrina var. alexandrina” in COCONUT

References (57)

  1. 10.1002/(SICI)1099-0801(199807/08)12:4<193::AID-BMC729>3.0.CO;2-7
  2. 10.1002/(SICI)1099-1573(199808)12:5<324::AID-PTR300>3.0.CO;2-2
  3. 10.1002/CHIN.200310223
  4. 10.1002/CHIN.200648207
  5. 10.1002/JCCS.200100154
  6. 10.1002/JPS.2600571138
  7. 10.1002/JPS.2600580211
  8. 10.1002/food.19880321030
  9. 10.1007/BF02319565
  10. 10.1007/bf02020635
  11. 10.1016/0003-2670(95)00034-W
  12. 10.1016/0021-9673(96)00141-0
  13. 10.1016/0031-9422(96)00102-1
  14. 10.1016/0378-8741(84)90016-3
  15. 10.1016/0378-8741(87)90005-5
  16. 10.1016/J.BMCL.2013.04.059
  17. 10.1016/J.FREERADBIOMED.2014.04.001
  18. 10.1016/J.LFS.2003.08.034
  19. 10.1016/J.VPH.2010.03.002
  20. 10.1016/S0021-9673(00)94500-X
  21. 10.1016/S0021-9673(99)00827-4
  22. 10.1016/S0040-4020(01)83338-X
  23. 10.1016/S0040-4020(02)00802-5
  24. 10.1016/S0367-326X(00)00335-X
  25. 10.1016/S0378-8741(00)00195-1
  26. 10.1016/S0960-894X(01)00318-3
  27. 10.1016/j.freeradbiomed.2014.04.001
  28. 10.1016/s0960-894x(01)00318-3
  29. 10.1021/JA01160A502
  30. 10.1021/JF049379P
  31. 10.1021/NP0301442
  32. 10.1021/NP50027A025
  33. 10.1021/NP50034A033
  34. 10.1021/NP50054A035
  35. 10.1021/NP50057A005
  36. 10.1021/NP50069A014
  37. 10.1021/NP50118A016
  38. 10.1021/ja01160a019
  39. 10.1021/np50069a014
  40. 10.1039/CT9130302006

Showing 40 of 57. 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.