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COCONUT Compound

icariside B5

CNP0201386.1 · C19H32O8 · View on COCONUT ↗

2D Structure

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Identifiers

Nameicariside B5
IUPAC Name(4~{S})-4-hydroxy-3,5,5-trimethyl-4-[(3~{R})-3-[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxybutyl]cyclohex-2-en-1-one
COCONUT IDCNP0201386.1
CAS114226-08-3
InChIKeyCZYPGTRKJFYXLT-SUHXYMONSA-N
InChIInChI=1S/C19H32O8/c1-10-7-12(21)8-18(3,4)19(10,25)6-5-11(2)26-17-16(24)15(23)14(22)13(9-20)27-17/h7,11,13-17,20,22-25H,5-6,8-9H2,1-4H3/t11-,13-,14-,15+,16-,17-,19-/m1/s1
SMILESCC1=CC(=O)CC(C)(C)[C@@]1(O)CC[C@@H](C)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

Properties

Molecular FormulaC19H32O8
Molecular Weight388.46
Exact Mass388.20972
Log P (ALogP)-0.35
TPSA136.68
H-Bond Donors / Acceptors5 / 8
Rotatable Bonds6
Lipinski's Rule of 5 Violations0
QED Drug-likeness0.42
NP-likeness2.59

Classification

NP PathwayTerpenoids
NP SuperclassApocarotenoids
NP ClassApocarotenoids(ε-)
Chemical SuperclassLipids and lipid-like molecules
Chemical ClassFatty Acyls
Chemical SubclassFatty acyl glycosides

Reported in GR-MAPs Plants

Ocimum sanctum as “Ocimum tenuiflorum” in COCONUT
Ocimum tenuiflorum as “Ocimum tenuiflorum” in COCONUT

References (14)

  1. 10.1002/1099-0690(200109)2001:18<3537::AID-EJOC3537>3.0.CO;2-A
  2. 10.1002/RCM.5123
  3. 10.1016/0031-9422(88)83141-8
  4. 10.1016/J.BMCL.2014.07.057
  5. 10.1016/J.PHYTOCHEM.2009.07.020
  6. 10.1016/S0031-9422(97)01112-6
  7. 10.1016/j.phytochem.2009.07.020
  8. 10.1080/14786410903244962
  9. 10.1248/CPB.36.2475
  10. 10.1248/CPB.51.286
  11. 10.1248/CPB.55.293
  12. 10.1248/CPB.56.1297
  13. 10.1248/CPB.57.636
  14. 10.1248/CPB.58.1646

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.