Monardaein
Basic information
- CAS
73545-87-6- Standard SMILES
O=C(O)CC(=O)OC[C@H]1O[C@@H](Oc2cc(O)cc3[o+]c(-c4ccc(O)cc4)c(O[C@@H]4O[C@H](COC(=O)/C=C/c5ccc(O)cc5)[C@@H](O)[C@H](O)[C@H]4O)cc23)[C@H](O)[C@@H](O)[C@@H]1OC(=O)CC(=O)O- InChIKey
HOQNHEQPPFYHLF-QBMVVDGVSA-O- Molecular formula
- C42H41O23+
- Average molar mass
- 913.8 g/mol
- Monoisotopic mass
- 913.20386255
Overview
Monardaein is an anthocyanin cation that is pelargonidin in which the hydroxy group at position 3 is substituted by a 6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranosyl group and the hydroxy group at position 5 is substituted by a 4,6-bis-O-(carboxyacetyl)-beta-D-glucopyranosyl group. It has a role as a plant metabolite. It is functionally related to a pelargonidin.
Names & identifiers
- Preferred name
- Monardaein
- IUPAC
- 3-[[(2R,3S,4R,5R,6S)-3-(2-carboxyacetyl)oxy-4,5-dihydroxy-6-[7-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxychromenylium-5-yl]oxyoxan-2-yl]methoxy]-3-oxopropanoic acid
Names & synonyms
MonardaeinMonardein cationMonardein ion739319-00-7UNII-3987B1IE653987B1IE6573545-87-6C087231-Benzopyrylium, 5-((4,6-bis-O-(2-carboxyacetyl)-beta-D-glucopyranosyl)oxy)-7-hydroxy-2-(4-hydroxyphenyl)-3-((6-O-((2E)-3-(4-hydroxyphenyl)-1-oxo-2-propen-1-yl)-beta-D-glucopyranosyl)oxy)-3-[[(2R,3S,4R,5R,6S)-3-(2-carboxyacetyl)oxy-4,5-dihydroxy-6-[7-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxychromenylium-5-yl]oxyoxan-2-yl]methoxy]-3-oxopropanoic acid7-hydroxy-2-(4-hydroxyphenyl)-3-({6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranosyl}oxy)-1-benzopyran-1-ium-5-yl 4,6-bis-O-(carboxyacetyl)-beta-D-glucopyranosideCHEBI:6972
Show more names
SCHEMBL30934000DTXSID80475095LMPK12010052Q271073771-BENZOPYRYLIUM, 5-((4,6-BIS-O-(2-CARBOXYACETYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-7-HYDROXY-2-(4-HYDROXYPHENYL)-3-((6-O-((2E)-3-(4-HYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-3,5,7,4'-Tetrahydroxyflavylium 3-(6"-p-coumarylglucoside)-5-(4-O,6-O-bismalonyl)-glucoside3-[[(2R,3S,4R,5R,6S)-3-(2-carboxyacetyl)oxy-4,5-dihydroxy-6-[7-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]tetrahydropyran-2-yl]oxy-chromenylium-5-yl]oxy-tetrahydropyran-2-yl]methoxy]-3-oxo-propanoic acid3-O-(6-O-trans-p-coumaryl-beta-D-glucopyranosyl)-5-O-(4,6-di-O-malonyl-beta-D-glucopyranosyl)pelargonidin
Properties
Computed structural properties
- Topological polar surface area
- 353 Ų
- Hydrogen bond donors
- 10
- Hydrogen bond acceptors
- 22
- Rotatable bonds
- 19
- Heavy atoms
- 65
- Formal charge
- 1
- Complexity
- 1,650
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Anthocyanidins [PK1201]
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