Peonidin 3-O-glucoside (YMDB01766)

Identification

YMDB ID

YMDB01766

Name

Peonidin 3-O-glucoside

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Peonidin 3-O-glucoside is an anthocyanin, which is a class of polyphenol. Peonidin 3-O-glucoside is one of the main anthocyanins found in grape. Anthocyanins are plant pigments found in many red berries including grape and grape skin. The cell wall of S. cerevisiae is permeable to anthocyanins and as a consequence the anthocyanins can be retained by yeast during wine-making; this adsorption can have an influence on wine color. Anthocyanins can react with yeast metabolites to form pyranoanthocyanins, which are more stable pigments formed during wine ageing and are of great importance for the color of aged wines. [PMID: 12822951] [PMID: 17303275]

Structure

MOL SDF PDB SMILES InChI

Synonyms

Peonidin-3-glucoside
3'-O-Methylcyanidin 3-O-beta-D-glucoside
Oxycoccicyanin
Peonidin 3-O-glucoside
3'-O-Methylcyanidin 3-O-b-D-glucoside
3'-O-Methylcyanidin 3-O-β-D-glucoside
Peonidin 3-O-beta-D-glucoside
Peonidin 3-O-b-D-glucoside
Peonidin 3-O-β-D-glucoside
Peonidin 3-glucoside
Peonidin-3-O-glucoside

CAS number

68795-37-9

Weight

Average: 463.4114
Monoisotopic: 463.124036578

InChI Key

ZZWPMFROUHHAKY-OUUKCGNVSA-O

InChI

InChI=1S/C22H22O11/c1-30-15-4-9(2-3-12(15)25)21-16(7-11-13(26)5-10(24)6-14(11)31-21)32-22-20(29)19(28)18(27)17(8-23)33-22/h2-7,17-20,22-23,27-29H,8H2,1H3,(H2-,24,25,26)/p+1/t17-,18-,19+,20-,22-/m1/s1

IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

Traditional IUPAC Name

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium

Chemical Formula

C₂₂H₂₃O₁₁

SMILES

COC1=C(O)C=CC(=C1)C1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C2C(O)=CC(O)=CC2=[O+]1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin-3-O-glycosides

Alternative Parents

Substituents

Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
7-hydroxyflavonoid
Hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
Anthocyanidin
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Methoxyphenol
1-benzopyran
Benzopyran
Methoxybenzene
Phenoxy compound
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Monosaccharide
Oxane
Heteroaromatic compound
Secondary alcohol
Polyol
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Primary alcohol
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:74793 )
monosaccharide derivative (CHEBI:74793 )
anthocyanin cation (CHEBI:74793 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.42 g/L	ALOGPS
logP	1.18	ALOGPS
logP	0.42	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	182.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.74 m³·mol⁻¹	ChemAxon
Polarizability	45.05 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-9203500000-46d99ce5e8628cbe9157	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-03di-2331029000-917c43b617d07d6f073b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0090100000-0807279ecd58dbe38f4e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0039100000-cbeb7a2ec27315d1575a	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0100900000-c6004bf80dd72ad2bd7b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1300900000-cfe5d43e5a5ed6973d3f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ot-8911000000-c56dc49b6c675b18b7bd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2300900000-9e7364bc1ea3ed714e5a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-6700900000-759ae58a8bfcf0669b11	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9300000000-c97a6a71b4c020768f6b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0019000000-484bf4d661bc90952ec8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0039200000-2f06e38c2f05d59c8b3b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w2d-6195100000-e9b66b1890c40defd541	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	74793
HMDB ID	HMDB0013689
Pubchem Compound ID	443654
Kegg ID	C12141
ChemSpider ID	24842280
FOODB ID	FDB017308
Wikipedia ID	Peonidin-3-O-glucoside
BioCyc ID	Not Available

Structure for #<Compound:0xa7eddfbc>