[(1S,4aR,5S,7aS)-5-hydroxy-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate

CNP0141197.3 · C22H26O11 · View on COCONUT ↗

2D Structure

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Identifiers

Name	[(1S,4aR,5S,7aS)-5-hydroxy-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
IUPAC Name	[(1~{S},4~{a}~{R},5~{S},7~{a}~{S})-5-hydroxy-1-[(2~{R},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,4~{a},5,7~{a}-tetrahydrocyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate
COCONUT ID	CNP0141197.3
InChIKey	GLACGTLACKLUJX-IDFFTYOGSA-N
InChI	InChI=1S/C22H26O11/c23-8-15-17(26)18(27)19(28)22(32-15)33-21-16-11(7-14(25)13(16)5-6-30-21)9-31-20(29)10-1-3-12(24)4-2-10/h1-7,13-19,21-28H,8-9H2/t13-,14+,15-,16+,17-,18+,19-,21-,22+/m0/s1
SMILES	O=C(OCC1=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)C1=CC=C(O)C=C1

Properties

Molecular Formula	C22H26O11
Molecular Weight	466.44
Exact Mass	466.14751
Log P (ALogP)	-1.23
TPSA	175.37
H-Bond Donors / Acceptors	6 / 11
Rotatable Bonds	6
Lipinski's Rule of 5 Violations	2
QED Drug-likeness	0.22
NP-likeness	2.23

Classification

NP Pathway	Terpenoids
NP Superclass	Monoterpenoids
NP Class	Iridoids monoterpenoids
Chemical Superclass	Lipids and lipid-like molecules
Chemical Class	Prenol lipids
Chemical Subclass	Terpene glycosides

Reported in GR-MAPs Plants

Vitex negundo	as “Vitex negundo” in COCONUT

References (1)

10.1016/J.BMCL.2006.09.051

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.

COCONUT Compound