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COCONUT Compound

57378-72-0

CNP0242282.2 · C25H24O12 · View on COCONUT ↗

2D Structure

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Identifiers

Name57378-72-0
IUPAC Name(1~{R},3~{R},4~{S},5~{R})-3,4-bis[[(~{E})-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxy-cyclohexanecarboxylic acid
COCONUT IDCNP0242282.2
CAS89886-30-6, 14534-61-3
InChIKeyUFCLZKMFXSILNL-RVXRWRFUSA-N
InChIInChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
SMILESO=C(/C=C/C1=CC=C(O)C(O)=C1)O[C@H]1[C@H](O)C[C@](O)(C(=O)O)C[C@H]1OC(=O)/C=C/C1=CC=C(O)C(O)=C1

Properties

Molecular FormulaC25H24O12
Molecular Weight516.46
Exact Mass516.12678
Log P (ALogP)1.03
TPSA211.28
H-Bond Donors / Acceptors7 / 11
Rotatable Bonds7
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.16
NP-likeness1.64

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassPhenylpropanoids (C6-C3)
NP ClassCinnamic acids and derivatives
Chemical SuperclassOrganic oxygen compounds
Chemical ClassOrganooxygen compounds
Chemical SubclassAlcohols and polyols

Reported in GR-MAPs Plants

Centella asiatica as “Centella asiatica” in COCONUT
Nicotiana tabacum as “Nicotiana tabacum” in COCONUT
Withania somnifera as “Withania somnifera” in COCONUT
Artemisia annua as “Artemisia annua; Artemisia annua L.” in COCONUT
Daucus carota as “Daucus carota” in COCONUT
Vitex negundo as “Vitex negundo” in COCONUT

References (57)

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  3. 10.1002/RCM.5123
  4. 10.1007/BF00629790
  5. 10.1007/s10600-005-0178-8
  6. 10.1016/0031-9422(88)80664-2
  7. 10.1016/0031-9422(95)00536-G
  8. 10.1016/0031-9422(96)00018-0
  9. 10.1016/J.BMCL.2007.10.046
  10. 10.1016/J.BMCL.2015.04.091
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  12. 10.1016/J.JPBA.2008.02.013
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  18. 10.1016/S0031-9422(00)84542-2
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  20. 10.1016/S0031-9422(00)90436-9
  21. 10.1016/S0031-9422(01)00066-8
  22. 10.1016/S0305-1978(97)00015-X
  23. 10.1016/S0367-326X(01)00331-8
  24. 10.1016/S0367-326X(02)00181-8
  25. 10.1016/j.bmcl.2014.09.087
  26. 10.1016/j.bmcl.2015.04.091
  27. 10.1021/JF020120L
  28. 10.1021/JF0485436
  29. 10.1021/JF060460X
  30. 10.1021/NP030177H
  31. 10.1021/NP050447R
  32. 10.1021/NP200646E
  33. 10.1021/NP980153O
  34. 10.1021/NP990538M
  35. 10.1021/acs.jnatprod.9b00674
  36. 10.1021/np050447r
  37. 10.1021/np200646e
  38. 10.1055/S-2001-18338
  39. 10.1055/S-2002-32566
  40. 10.1055/S-2004-832645

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.