Malonylgenistin

HCID 15934091CAS 51011-05-3
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Basic information

Standard SMILES
O=C(O)CC(=O)OC[C@H]1O[C@@H](Oc2cc(O)c3c(=O)c(-c4ccc(O)cc4)coc3c2)[C@H](O)[C@@H](O)[C@@H]1O
InChIKey
FRAUJUKWSKMNJY-RSEYPYQYSA-N
Molecular formula
C24H22O13
Average molar mass
518.4 g/mol
Monoisotopic mass
518.10604076

Overview

Malonylgenistin is a glycosyloxyisoflavone that is genistin in which the hydroxy hydrogen at position 6'' has been replaced by a malonyl group. It has a role as a plant metabolite. It is a beta-D-glucoside, a malonate ester, a hydroxyisoflavone, a monosaccharide derivative and a glycosyloxyisoflavone. It is functionally related to a genistein 7-O-beta-D-glucoside.

Names & identifiers

Preferred name
Malonylgenistin
IUPAC
3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]propanoic acid

Names & synonyms

6''-O-MALONYLGENISTINMalonylgenistin51011-05-3Genistin MalonateGenistin 6''-O-Malonate7-O-Glucosyl-6''-malonyl Genistein2AUB85VT2KCHEBI:80372Genistein-7-o-beta-D-glucosyl-6''-o-malonateDTXSID2013168543-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]propanoic acid5-Hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-O-(carboxylatoacetyl)hexopyranoside
Show more names
Propanedioic acid, 6'-ester with 7-(beta-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one3-oxo-3-(((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl)oxyoxan-2-yl)methoxy)propanoic acidRefChem:925238DTXCID901746680Malonyl genistin (constituent of soy isoflavones)Malonyl-genistin6-O-MALONYLGENISTIN, FREE ACID3-Oxo-3-(((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-2-yl)methoxy)propanoic acid

Database identifiers

CAS
51011-05-3
PubChem CID
15934091
DTXSID
DTXSID201316854
ChEMBL
CHEMBL3426722
ChEBI
CHEBI:80372
UNII
2AUB85VT2K
Nikkaji
J485.134J

Properties

Computed structural properties

XLogP
0.6
Topological polar surface area
210 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
13
Rotatable bonds
8
Heavy atoms
37

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205]

Safety & regulation

Hazard information

Regulatory Information · 1 item

4H-1-Benzopyran-4-one, 7-6-O-(carboxyacetyl)-.beta.-D-glucopyranosyloxy-5-hydroxy-3-(4-hydroxyphenyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Related reactions

3 records
New reaction record

Linked notes

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