5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ4-chromen-1-ylium chloride

• ChemBase ID: 154141
• Molecular Formular: C23H25ClO12
• Molecular Mass: 528.8904
• Monoisotopic Mass: 528.10345392
• SMILES: COc1cc(cc(c1O)OC)c1c(cc2c(cc(cc2[o+]1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O.[Cl-]
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2cc3c(O)cc(cc3[o+]c2c2cc(OC)c(c(c2)OC)O)O)[C@@H]([C@H]([C@@H]1O)O)O.[Cl-]
• InChI: InChI=1S/C23H24O12.ClH/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23;/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27);1H/t17-,19-,20+,21-,23-;/m1./s1
• InChIKey: YDIKCZBMBPOGFT-DIONPBRTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ^4-chromen-1-ylium chloride
• IUPAC Traditional name: malvidin-3-glucoside chloride
• Synonyms: Cyclamin chloride; Enin chloride; Malvidin-3-O-glucoside chloride; Oenin chloride

Database IDs

• CAS Number: 7228-78-6
• EC Number: 230-631-9
• MDL Number: MFCD00185576
• PubChem SID: 162248280; 24886454
• PubChem CID: 11249520

CALCULATED PROPERTIES

• Acid pKa: 6.382928
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): 0.11210496
• LogD (pH = 7.4): -1.1929935
• Log P: 0.166
• Molar Refractivity: 127.203 cm^3
• Polarizability: 48.460262 Å^3
• Polar Surface Area: 191.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C23H25ClO12

DETAILS

Sigma Aldrich - 72813

Biochem/physiol Actions
Anthocyanin. Studied for its neuroprotective properties.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 72813.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.