Isoliquiritin

HCID 5318591

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Basic information

CAS: 5041-81-6
Standard SMILES: O=C(/C=C/c1ccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1)c1ccc(O)cc1O
InChIKey: YNWXJFQOCHMPCK-LXGDFETPSA-N
Molecular formula: C21H22O9
Average molar mass: 418.4 g/mol
Monoisotopic mass: 418.12638228

Overview

Isoliquiritin is a monosaccharide derivative that is trans-chalcone substituted by hydroxy groups at positions 2' and 4' and a beta-D-glucopyranosyloxy group at position 4 respectively. It has a role as an antineoplastic agent and a plant metabolite. It is a beta-D-glucoside, a member of chalcones, a member of resorcinols and a monosaccharide derivative. It is functionally related to a trans-chalcone.

Names & identifiers

Preferred name: Isoliquiritin
IUPAC: (E)-1-(2,4-dihydroxyphenyl)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one
English name: neoisoliquiritin
Molecular formula: C21H22O9
Molecular weight: 418.39

Names & synonyms

Isoliquiritin5041-81-6IsoliquiritosideUNII-2Y348H1V4W4-[(1E)-3-(2,4-dihydroxyphenyl)-3-oxoprop-1-en-1-yl]phenyl beta-D-glucopyranosideCHEBI:808394-beta-D-glucopyranosyloxy-2',4'-dihydroxy-trans-chalcone2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(4-(beta-D-glucopyranosyloxy)phenyl)-, (2E)-4-((1E)-3-(2,4-dihydroxyphenyl)-3-oxoprop-1-en-1-yl)phenyl beta-D-glucopyranosideRefChem:402937014-39-3MFCD00272145

Show more names

neoisoliquiritin1-[4-(β-D-glucopyranosyloxy)-2-hydroxyphenyl]-3-(4-hydroxyphenyl)-1-(2,4-Dihydroxyphenyl)-3-[4-(beta-D-glucopyranosyloxy)phenyl]-2-propen-1-one2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-[4-(β-D-glucopyranosyloxy)phenyl]- (9CI)

2Y348H1V4WNeoisoliquiritigenin(E)-1-(2,4-Dihydroxyphenyl)-3-(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)prop-2-en-1-one(E)-1-(2,4-dihydroxyphenyl)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]prop-2-en-1-one(E)-1-(2,4-dihydroxyphenyl)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-oneIsoliquiriiinIsoliquiritin?2-PROPEN-1-ONE, 1-(2,4-DIHYDROXYPHENYL)-3-(4-(.BETA.-D-GLUCOPYRANOSYLOXY)PHENYL)-, (2E)-

Database identifiers

CAS: 5041-81-6、7014-39-3
PubChem CID: 5318591
DTXSID: DTXSID901317746
ChEMBL: CHEMBL599763
ChEBI: CHEBI:80839
UNII: 2Y348H1V4W
Nikkaji: J2.434.257C、J27.434H

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 157 Å²
Hydrogen bond donors: 6
Hydrogen bond acceptors: 9
Rotatable bonds: 6
Heavy atoms: 30
Formal charge: 0
Complexity: 589

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]

Physicochemical properties

Melting point: 230 · 230-232℃
Boiling point: 743.5 · 743.5±60.0 °C(Predicted)
Density: 1.528 · 1.528
pka: 7.36 · 7.36±0.35(Predicted)

Chemistry & industry

Applications

Usesneoisoliquiritin inhibits tumor progression by targeting GRP78-β-catenin signaling in human breast cancer cell xenograft mouse model. A cancer chemopreventive agent.

Suppliers82 total

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]

上海纯优生物科技有限公司18302135232 18302135232 · [email protected]

成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]

江苏永健医药科技有限公司17701422015

Additional notes · 1 item

DefinitionChEBI: Isoliquiritin is a monosaccharide derivative that is trans-chalcone substituted by hydroxy groups at positions 2' and 4' and a beta-D-glucopyranosyloxy group at position 4 respectively. It has a role as an antineoplastic agent and a plant metabolite. It is a member of chalcones, a member of resorcinols, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a trans-chalcone.

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