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COCONUT Compound

Negundoside

CNP0167903.3 · C23H28O12 · View on COCONUT ↗

2D Structure

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Identifiers

NameNegundoside
IUPAC Name(1~{S},4~{a}~{S},7~{S},7~{a}~{S})-1-[(2~{S},3~{R},4~{S},5~{S},6~{R})-4,5-dihydroxy-3-(4-hydroxybenzoyl)oxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-7-hydroxy-7-methyl-4~{a},5,6,7~{a}-tetrahydro-1~{H}-cyclopenta[c]pyran-4-carboxylic acid
COCONUT IDCNP0167903.3
CAS82451-20-5
InChIKeyRFCSGMIUBXUYSE-KLZCBZFCSA-N
InChIInChI=1S/C23H28O12/c1-23(31)7-6-12-13(19(28)29)9-32-21(15(12)23)35-22-18(17(27)16(26)14(8-24)33-22)34-20(30)10-2-4-11(25)5-3-10/h2-5,9,12,14-18,21-22,24-27,31H,6-8H2,1H3,(H,28,29)/t12-,14-,15-,16-,17+,18-,21+,22+,23+/m1/s1
SMILESC[C@]1(O)CC[C@@H]2C(C(=O)O)=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)C3=CC=C(O)C=C3)[C@@H]21

Properties

Molecular FormulaC23H28O12
Molecular Weight496.47
Exact Mass496.15808
Log P (ALogP)-0.52
TPSA192.44
H-Bond Donors / Acceptors6 / 11
Rotatable Bonds6
Lipinski's Rule of 5 Violations2
QED Drug-likeness0.28
NP-likeness2.43

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

Vitex negundo as “Vitex negundo” in COCONUT

References (10)

  1. 10.1016/0031-9422(83)85054-7
  2. 10.1016/J.BMCL.2006.09.051
  3. 10.1016/J.JPBA.2011.12.007
  4. 10.1016/S0031-9422(00)80420-3
  5. 10.1016/S0031-9422(00)95267-1
  6. 10.1016/j.phymed.2013.01.003
  7. 10.1016/s0031-9422(00)95267-1
  8. 10.1021/NP040117R
  9. 10.1055/S-2006-960800
  10. 10.1080/14786410802696494

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.