Afzelechin

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Basic information

CAS: 2545-00-8
Standard SMILES: Oc1ccc([C@H]2Oc3cc(O)cc(O)c3C[C@@H]2O)cc1
InChIKey: RSYUFYQTACJFML-DZGCQCFKSA-N
Molecular formula: C15H14O5
Average molar mass: 274.27 g/mol
Monoisotopic mass: 274.08412354

Overview

Afzelechin is a tetrahydroxyflavan that is (2S)-flavan substituted by hydroxy groups at positions 3, 5, 7 and 4' respectively. It has a role as an EC 3.2.1.20 (alpha-glucosidase) inhibitor and a plant metabolite. It is a catechin and a tetrahydroxyflavan. It derives from a hydride of a (2S)-flavan.

Names & identifiers

Preferred name: Afzelechin
IUPAC: (2R,3S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
English name: AFZELECHIN
Molecular formula: C15H14O5
Molecular weight: 274.27

Names & synonyms

(+)-AfzelechinAFZELECHIN2545-00-83,4',5,7-Flavantetrol, (+)-NSC-135065W782YDV47U3,5,7,4'-TetrahydroxyflavanCHEBI:25072H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(4-hydroxyphenyl)-, (2R,3S)-2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(4-hydroxyphenyl)-, (2R-trans)-(2R,3S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triolRefChem:110060

Show more names

(+)-afzelichin(2R)-2α-(4-Hydroxyphenyl)chroman-3β,5,7-triol2H-1-Benzopyran-3,5,7-triol,3,4-dihydro-2-(4-hydroxyphenyl)-, (2R,3S)[2R,3S,(+)]-3,4-Dihydro-2-(4-hydroxyphenyl)-2H-1-benzopyran-3,5,7-triol

2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(4-hydroxyphenyl)-, (2R,3R)-(2R,3S)-2-(4-hydroxyphenyl)chromane-3,5,7-triol(2R,3S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triolUNII-W782YDV47U(+)-Afzelechin ;NSC 135065(2R,3S)-afzelechinSCHEMBL445728orb1684785

Database identifiers

Properties

Computed structural properties

XLogP: 0.7
Topological polar surface area: 90.2 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 5
Rotatable bonds: 1
Heavy atoms: 20
Formal charge: 0
Complexity: 328

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavans, Flavanols and Leucoanthocyanidins [PK1202]

Physicochemical properties

Melting point: 252 · 252-254 °C (decomp)
Boiling point: 583.4 · 583.4±50.0 °C(Predicted)
Density: 1.492 · 1.492±0.06 g/cm3(Predicted)
solubility: Soluble in DMSO
form: Powder
pka: 9 · 9+-.0.60(Predicted)
color: White to light brown
InChI: InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15+/m0/s1
InChIKey: RSYUFYQTACJFML-DZGCQCFKSA-N
SMILES: [C@H]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2C[C@@H]1O
FDA UNII: 782 YDV47U · W782YDV47U

Chemistry & industry

Applications · 1 item

Uses(+)-Afzelechin, isolated from rhizomes of Bergenia ligulata, is an alpha-glucosidase activity inhibitor with an ID50 (50% inhibition dose) value of 0.13 mM. (+)-Afzelechin can delay the absorption of carbohydrates in food to suppress postprandial hyperglycemia and hyperinsulinemia[1].

Additional notes

DefinitionChEBI: A tetrahydroxyflavan that is (2S)-flavan substituted by hydroxy groups at positions 3, 5, 7 and 4' respectively.

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