Sakuranin

HCID 73607

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Basic information

CAS: 529-39-5
Standard SMILES: COc1cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2c(c1)O[C@H](c1ccc(O)cc1)CC2=O
InChIKey: NEPMMBQHELYZIW-YMTXFHFDSA-N
Molecular formula: C22H24O10
Average molar mass: 448.4 g/mol
Monoisotopic mass: 448.13694696

Overview

Sakuranin is a flavanone glycoside that is sakuranetin attached to a beta-D-glucopyranosyl residue at position 5 via a glycosidic linkage. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor and a plant metabolite. It is a member of 4'-hydroxyflavanones, a monomethoxyflavanone, a monohydroxyflavanone and a flavanone glycoside. It is functionally related to a sakuranetin.

Names & identifiers

Preferred name: Sakuranin
IUPAC: (2S)-2-(4-hydroxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one

Names & synonyms

SAKURANIN529-39-5NSC 40730859YX7QWM4SCHEBI:81054NSC-407308(2S)-2-(4-hydroxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one(2S)-2-(4-hydroxyphenyl)-7-methoxy-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2,3-dihydrochromen-4-oneRefChem:180868NSC407308(S)-5-(beta-D-Glucopyranosyloxy)-2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one(2S)-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl beta-D-glucopyranoside

Show more names

4H-1-Benzopyran-4-one, 5-(.beta.-D-glucopyranosyloxy)-2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-, (2S)-UNII-59YX7QWM4SCHEMBL495847SCHEMBL29420388DTXSID209673634H-1-Benzopyran-4-one, 5-(beta-D-glucopyranosyloxy)-2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-, (S)-C17391SAKURANETIN, 5-.BETA.-D-GLUCOPYRANOSIDE

Database identifiers

CAS: 529-39-5

Properties

Computed structural properties

XLogP: 0.4
Topological polar surface area: 155 Å²
Hydrogen bond donors: 5
Hydrogen bond acceptors: 10
Rotatable bonds: 5
Heavy atoms: 32
Formal charge: 0
Complexity: 638

Related reactions

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Compound notes

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