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COCONUT Compound

Aucubin

CNP0242593.1 · C15H22O9 · View on COCONUT ↗

2D Structure

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Identifiers

NameAucubin
IUPAC Name(2~{S},3~{R},4~{S},5~{S},6~{R})-2-[[(1~{S},4~{a}~{R},5~{S},7~{a}~{S})-5-hydroxy-7-(hydroxymethyl)-1,4~{a},5,7~{a}-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
COCONUT IDCNP0242593.1
CAS479-98-1
InChIKeyRJWJHRPNHPHBRN-FKVJWERZSA-N
InChIInChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1
SMILESOCC1=C[C@@H](O)[C@@H]2C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H]12

Properties

Molecular FormulaC15H22O9
Molecular Weight346.33
Exact Mass346.12638
Log P (ALogP)-2.80
TPSA149.07
H-Bond Donors / Acceptors6 / 9
Rotatable Bonds4
Lipinski's Rule of 5 Violations1
QED Drug-likeness0.30
NP-likeness3.15

Classification

NP PathwayTerpenoids
NP SuperclassMonoterpenoids
NP ClassIridoids monoterpenoids
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassPrenol lipids
Chemical SubclassTerpene glycosides

Reported in GR-MAPs Plants

Plantago ovata as “Plantago ovata” in COCONUT
Vitex negundo as “Vitex negundo” in COCONUT

References (176)

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  2. 10.1002/9780470744307.gat218
  3. 10.1002/CHIN.200303149
  4. 10.1002/CHIN.200340174
  5. 10.1002/CHIN.200927180
  6. 10.1002/HLCA.19810640110
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  9. 10.1002/PCA.2800020107
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  12. 10.1007/978-1-4757-2451-6
  13. 10.1007/BF00564831
  14. 10.1007/BF00579633
  15. 10.1007/BF00579788
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  17. 10.1007/BF00602483
  18. 10.1007/BF01167570
  19. 10.1007/BF01373801
  20. 10.1007/BF02164691
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  22. 10.1007/S10600-009-9420-0
  23. 10.1007/S10600-011-9920-6
  24. 10.1007/S11418-006-0027-5
  25. 10.1016/0021-9673(95)01057-2
  26. 10.1016/0031-9422(72)85053-2
  27. 10.1016/0031-9422(80)87017-8
  28. 10.1016/0031-9422(81)80054-4
  29. 10.1016/0031-9422(82)80029-0
  30. 10.1016/0031-9422(83)80015-6
  31. 10.1016/0031-9422(88)80764-7
  32. 10.1016/0031-9422(90)85134-2
  33. 10.1016/0031-9422(90)85366-N
  34. 10.1016/0031-9422(91)83660-D
  35. 10.1016/0031-9422(91)85040-7
  36. 10.1016/0031-9422(92)80017-9
  37. 10.1016/0031-9422(92)80183-F
  38. 10.1016/0031-9422(92)80354-H
  39. 10.1016/0031-9422(92)80441-G
  40. 10.1016/0031-9422(93)85028-P

Showing 40 of 176. 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.