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COCONUT Compound

Procyanidin C1

CNP0173918.2 · C45H38O18 · View on COCONUT ↗

2D Structure

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Identifiers

NameProcyanidin C1
IUPAC Name(2~{R},3~{R},4~{S})-2-(3,4-dihydroxyphenyl)-4-[(2~{R},3~{R})-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]-8-[(2~{R},3~{R},4~{R})-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-4-yl]chromane-3,5,7-triol
COCONUT IDCNP0173918.2
CAS37064-30-5
InChIKeyMOJZMWJRUKIQGL-XILRTYJMSA-N
InChIInChI=1S/C45H38O18/c46-18-10-27(54)33-32(11-18)61-42(16-2-5-21(48)25(52)8-16)39(59)37(33)35-29(56)14-30(57)36-38(40(60)43(63-45(35)36)17-3-6-22(49)26(53)9-17)34-28(55)13-23(50)19-12-31(58)41(62-44(19)34)15-1-4-20(47)24(51)7-15/h1-11,13-14,31,37-43,46-60H,12H2/t31-,37-,38+,39-,40-,41-,42-,43-/m1/s1
SMILESOC1=CC(O)=C2C(=C1)O[C@H](C1=CC=C(O)C(O)=C1)[C@H](O)[C@H]2C1=C(O)C=C(O)C2=C1O[C@H](C1=CC=C(O)C(O)=C1)[C@H](O)[C@H]2C1=C(O)C=C(O)C2=C1O[C@H](C1=CC=C(O)C(O)=C1)[C@H](O)C2

Properties

Molecular FormulaC45H38O18
Molecular Weight866.78
Exact Mass866.20581
Log P (ALogP)4.44
TPSA331.14
H-Bond Donors / Acceptors15 / 18
Rotatable Bonds5
Lipinski's Rule of 5 Violations3
QED Drug-likeness0.11
NP-likeness1.32

Classification

NP PathwayShikimates and Phenylpropanoids
NP SuperclassFlavonoids
NP ClassProanthocyanins
Chemical SuperclassPhenylpropanoids and polyketides
Chemical ClassFlavonoids
Chemical SubclassBiflavonoids and polyflavonoids

Reported in GR-MAPs Plants

Daucus carota as “Daucus carota” in COCONUT
Cinnamomum verum as “Cinnamomum zeylanicum” in COCONUT

References (49)

  1. 10.1002/(SICI)1099-1565(199801/02)9:1<21::AID-PCA377>3.0.CO;2-W
  2. 10.1002/(SICI)1099-1565(200003/04)11:2<106::AID-PCA496>3.0.CO;2-O
  3. 10.1002/HLCA.200890142
  4. 10.1007/BF02262390
  5. 10.1007/S002170100354
  6. 10.1016/0031-9422(75)85197-1
  7. 10.1016/0031-9422(82)80150-7
  8. 10.1016/0031-9422(90)80121-V
  9. 10.1016/0031-9422(92)80317-8
  10. 10.1016/0031-9422(95)00855-1
  11. 10.1016/J.FITOTE.2009.08.015
  12. 10.1016/J.JEP.2005.02.029
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  14. 10.1016/S0021-9673(01)87172-7
  15. 10.1016/S0021-9673(99)00043-6
  16. 10.1016/S0021-9673(99)00281-2
  17. 10.1016/S0021-9673(99)00684-6
  18. 10.1016/S0031-9422(00)00192-8
  19. 10.1016/S0031-9422(00)83018-6
  20. 10.1016/S0031-9422(00)83483-4
  21. 10.1016/S0031-9422(00)95213-0
  22. 10.1016/S0031-9422(02)00051-1
  23. 10.1016/S0031-9422(02)00172-3
  24. 10.1016/S0031-9422(97)00489-5
  25. 10.1016/S0944-7113(98)80010-X
  26. 10.1021/JF00048A016
  27. 10.1021/JF000549H
  28. 10.1021/JF011083L
  29. 10.1021/JF050457Y
  30. 10.1021/JF970468U
  31. 10.1021/JF990665O
  32. 10.1039/P19830002139
  33. 10.1039/P19840000343
  34. 10.1055/S-0031-1299862
  35. 10.1055/S-0042-102660
  36. 10.1055/S-2006-961020
  37. 10.1078/0944-7113-00003
  38. 10.1080/10826079208018822
  39. 10.1111/J.1745-4557.2003.TB00243.X
  40. 10.1248/CPB.30.4277

Showing 40 of 49. 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.