An official website of the United States government

2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenium-3-yl 6-O-[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside

PubChem CID
72193655
Structure
2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenium-3-yl 6-O-[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside_small.png
2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenium-3-yl 6-O-[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside_3D_Structure.png
Molecular Formula
Synonyms
  • CHEBI:75708
  • petunidin-3-O-(6-O-cis-p-coumaryl-beta-D-glucoside)
  • petunidin 3-O-(6-O-(Z)-4-coumaroyl-beta-D-glucoside)
  • 2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenium-3-yl 6-O-[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside
Molecular Weight
625.6 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2013-12-10
  • Modify:
    2025-01-04
Description
Petunidin 3-O-(6-O-(Z)-4-coumaroyl-beta-D-glucoside) is an anthocyanin cation that is petunidin substituted at position 3 by a 6-O-(cis-4 coumaryl)-beta-D-glucosyl residue. It has a role as a metabolite. It is a beta-D-glucoside, an anthocyanin cation, a cinnamate ester, an aromatic ether and a polyphenol. It is functionally related to a cis-4-coumaric acid and a petunidin.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenium-3-yl 6-O-[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (Z)-3-(4-hydroxyphenyl)prop-2-enoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C31H28O14/c1-41-22-9-15(8-20(35)26(22)37)30-23(12-18-19(34)10-17(33)11-21(18)43-30)44-31-29(40)28(39)27(38)24(45-31)13-42-25(36)7-4-14-2-5-16(32)6-3-14/h2-12,24,27-29,31,38-40H,13H2,1H3,(H4-,32,33,34,35,36,37)/p+1/t24-,27-,28+,29-,31-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

KTFQEFWNLAUGAX-VEZAKBLNSA-O
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

COC1=CC(=CC(=C1O)O)C2=[O+]C3=CC(=CC(=C3C=C2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)/C=C\C5=CC=C(C=C5)O)O)O)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C31H29O14+
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
625.6 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
13
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
625.15573059 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
625.15573059 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
217Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
45
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
1
Reference
Computed by PubChem
Property Name
Complexity
Property Value
989
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
5
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

5 Classification

5.1 ChEBI Ontology

6 Information Sources

  1. ChEBI
    Petunidin 3-O-(6-O-(Z)-4-coumaroyl-beta-D-glucoside)
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:75708
  2. Wikidata
    2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenium-3-yl 6-O-[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside
    https://www.wikidata.org/wiki/Q106010170
    2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxychromenium-3-yl 6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside
    https://www.wikidata.org/wiki/Q106010171
  3. PubChem
CONTENTS