Showing Compound Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside (FDB017312)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:01 UTC

Update date

2019-11-26 03:14:38 UTC

Primary ID

FDB017312

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside

Description

Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside has been detected, but not quantified in, common grapes (Vitis vinifera) and fruits. This could make peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside.

CAS Number

51939-65-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
3,4',5,7-Tetrahydroxy-3'-methoxyflavylium(1+)	HMDB
3,4',5,7-Tetrahydroxy-3'-methoxyflavylium(1+); 3-O-[4-Hydroxycinnamoyl-(->6)-b-D-glucopyranoside], 5-O-b-D-glucopyranoside	db_source
3-O-[4-Hydroxycinnamoyl-(->6)-b-D-glucopyranoside], 5-O-b-D-glucopyranoside	HMDB
Peonidin 3-(6''-P-coumarylglucoside)-5-glucoside	HMDB
Peonidin 3-(6''-p-coumarylglucoside)-5-glucoside	biospider

Showing 1 to 5 of 5 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.071 g/L	ALOGPS
logP	2.77	ALOGPS
logP	2.49	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	6.66	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	267.66 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	197.55 m³·mol⁻¹	ChemAxon
Polarizability	76.99 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C38H41O17

IUPAC name

5-{[(2S,4R,5S)-4,5-dihydroxy-6-(hydroxymethyl)-3-methyloxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

InChI Identifier

InChI=1S/C38H40O17/c1-17-31(44)32(45)28(15-39)54-37(17)52-25-13-21(41)12-24-22(25)14-27(36(51-24)19-6-9-23(42)26(11-19)49-2)53-38-35(48)34(47)33(46)29(55-38)16-50-30(43)10-5-18-3-7-20(40)8-4-18/h3-14,17,28-29,31-35,37-39,44-48H,15-16H2,1-2H3,(H2-,40,41,42,43)/p+1/t17?,28?,29-,31-,32-,33-,34+,35-,37-,38-/m1/s1

InChI Key

UYFNRLODXGXIBD-VEMHFVEPSA-O

Isomeric SMILES

COC1=C(O)C=CC(=C1)C1=[O+]C2=C(C=C1O[C@@H]1O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)[C@H](O)[C@H]1O)C(O[C@@H]1OC(CO)[C@@H](O)[C@H](O)C1C)=CC(O)=C2

Average Molecular Weight

769.7219

Monoisotopic Molecular Weight

769.234374886

Classification

Description

Belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These are anthocyanidin 3-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Anthocyanidin 3-O-6-p-coumaroyl glycosides

Alternative Parents

Substituents

Anthocyanidin 3-o-6-p-coumaroyl-glycoside
Anthocyanin
Anthocyanidin-5-o-glycoside
Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3p-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
Hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Coumaric acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Methoxyphenol
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Polyol
Acetal
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carbonyl group
Primary alcohol
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 57.59%; H 5.09%; O 37.32%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TBDMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TBDMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TBDMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TBDMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside, TBDMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0100000900-d6b8f85ed96ef6451c9c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-1200000900-5e3797d874b3616e3214	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03du-7900000300-fc49e15b8ea9112d682d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0100000900-4e4d3f5cdcf8e2851cd1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9100000200-d3588396098a799f6f4e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0596-9100001000-e629a85bb74b8cc72df0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-0500901500-d10548f9cdaf11384321	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dm-0402903400-65b90ce62285af605cd2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0910112100-69e30e3a53de979fdebc	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB38092

CRC / DFC (Dictionary of Food Compounds) ID

CNL87-O:KXB46-F

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00006867

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside (FDB017312)

Structure for FDB017312 (Peonidin 3-(6''-p-coumaroyl-glucoside) 5-glucoside)