(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro(4,4,6-2H3)-2H-1-benzopyran-3,5,7-triol

• ChemBase ID: 163856
• Molecular Formular: C15H14O6
• Molecular Mass: 290.26806
• Monoisotopic Mass: 290.07903817
• SMILES: c1(cc(c2c(c1)O[C@@H]([C@H](C2)O)c1ccc(c(c1)O)O)O)O
• Canonical SMILES: Oc1cc2O[C@H](c3ccc(c(c3)O)O)[C@H](Cc2c(c1)O)O
• InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1
• InChIKey: PFTAWBLQPZVEMU-DZGCQCFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro(4,4,6-^2H₃)-2H-1-benzopyran-3,5,7-triol
• IUPAC Traditional name: (2R,3S)-2-(3,4-dihydroxyphenyl)-2,3-dihydro(4,4,6-^2H₃)-1-benzopyran-3,5,7-triol
• Synonyms: (2R,3S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol-d3; (+)-(2R:3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol-d3; D-Catechin-d3; (+)-Catechol-d3; (+)-Cianidanol-d3; (+)-Cyanidan-3-ol-d3; (+)-Cyanidanol-d3; (2R,3S)-(+)-Catechin-d3; (+)-3-Cyanidanol-d3; (+)-Biocatechin-d3; Catechin-d3; Catechinic Acid-d3; Catechuic Acid-d3; Catergen-d3; Cianidanol-d3; Cyanidanol-d3; Cyanidol-d3; D-(+)-Catechin-d3; Dexcyanidanol-d3; HB-MC-TS 35-d3; NSC 2819-d3; P 70A-d3; Teafuran 30A-d3; Teafuran 30E-d3; trans-(+)-3,3',4',5,7-Flavanpentol-d3; (+)-Catechin-d3

Database IDs

• PubChem SID: 162257991
• PubChem CID: 71314581

CALCULATED PROPERTIES

• Acid pKa: 9.004574
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 1.7949721
• LogD (pH = 7.4): 1.784451
• Log P: 1.795107
• Molar Refractivity: 73.9997 cm^3
• Polarizability: 28.501688 Å^3
• Polar Surface Area: 110.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C217502

Labelled (+)-Catechin (C217500). (+)-Catechin is a flavonoid found primarily in higher woody plants as (+)-Catechin along with (-)-Epicatechin (cis form). Antidiarrheal.

REFERENCES

• Das, S., Biochem. J., et al.: 125, 417 (1971)
• Das, N.P., et al.: Biochem. Pharmacol., 20, 3435 (1971)