Showing Compound Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxy-3-methoxy-(E)-cinnamoyl-(->6)]-b-D-glucopyranoside] 5-O-(6-O-malonyl-b-D-glucopyranoside) (FDB014137)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:06 UTC

Update date

2019-11-26 03:09:34 UTC

Primary ID

FDB014137

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxy-3-methoxy-(E)-cinnamoyl-(->6)]-b-D-glucopyranoside] 5-O-(6-O-malonyl-b-D-glucopyranoside)

Description

Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxy-3-methoxy-(E)-cinnamoyl-(->6)]-b-D-glucopyranoside] 5-O-(6-O-malonyl-b-D-glucopyranoside) 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. Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxy-3-methoxy-(E)-cinnamoyl-(->6)]-b-D-glucopyranoside] 5-O-(6-O-malonyl-b-D-glucopyranoside) has been detected, but not quantified in, brassicas. This could make pelargonidin 3-O-[b-D-glucopyranosyl-(1->2)-[4-hydroxy-3-methoxy-(e)-cinnamoyl-(->6)]-b-D-glucopyranoside] 5-O-(6-O-malonyl-b-D-glucopyranoside) a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxy-3-methoxy-(E)-cinnamoyl-(->6)]-b-D-glucopyranoside] 5-O-(6-O-malonyl-b-D-glucopyranoside).

CAS Number

218963-77-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
3,4',5,7-Tetrahydroxyflavylium(1+), 8ci	HMDB
3,4',5,7-Tetrahydroxyflavylium(1+), 8CI; 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxy-3-methoxycinnamoyl-(->6)]-b-D-glucopyranoside](E-), 5-O-(6-O-malonyl-b-D-glucopyranoside)	db_source
3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxy-3-methoxycinnamoyl-(->6)]-b-D-glucopyranoside](e-), 5-O-(6-O-malonyl-b-D-glucopyranoside)	HMDB

Showing 1 to 3 of 3 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	1.27	ALOGPS
logP	-0.66	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	410.41 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	242.34 m³·mol⁻¹	ChemAxon
Polarizability	97.7 Å³	ChemAxon
Number of Rings	7	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

C46H51O26

IUPAC name

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

InChI Identifier

InChI=1S/C46H50O26/c1-63-26-10-18(2-8-23(26)50)3-9-32(53)64-16-30-36(57)39(60)43(72-45-41(62)37(58)34(55)28(15-47)69-45)46(71-30)68-27-13-22-24(66-42(27)19-4-6-20(48)7-5-19)11-21(49)12-25(22)67-44-40(61)38(59)35(56)29(70-44)17-65-33(54)14-31(51)52/h2-13,28-30,34-41,43-47,55-62H,14-17H2,1H3,(H3-,48,49,50,51,52,53)/p+1

InChI Key

XGPCPGROCKPKCA-UHFFFAOYSA-O

Isomeric SMILES

COC1=CC(\C=C\C(=O)OCC2OC(OC3=CC4=C(OC5OC(COC(=O)CC(O)=O)C(O)C(O)C5O)C=C(O)C=C4[O+]=C3C3=CC=C(O)C=C3)C(OC3OC(CO)C(O)C(O)C3O)C(O)C2O)=CC=C1O

Average Molecular Weight

1019.8815

Monoisotopic Molecular Weight

1019.266856804

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

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 54.17%; H 5.04%; O 40.79%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-016r-9300000000-938d8c274b924e459bb4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-6900000000-ffabe66915b6e9e14f38	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0lxx-9800000000-582ce8c3fa15ded7c191	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0089-9200000000-d6366b0a8092db3565c0	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-9200000001-b540bf5bf2eea54694cf	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ed-9710000010-ec041b863d04506acf45	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0g4i-9310020513-a3f7a86285d49dee1d03	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1100031900-23e3e5cd05047a88be1c	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dj-3930020422-b64ea04903a6439101ca	2021-09-21	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

HMDB35453

CRC / DFC (Dictionary of Food Compounds) ID

HGV59-L:JOD60-T

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

Showing Compound Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxy-3-methoxy-(E)-cinnamoyl-(->6)]-b-D-glucopyranoside] 5-O-(6-O-malonyl-b-D-glucopyranoside) (FDB014137)

Structure for FDB014137 (Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxy-3-methoxy-(E)-cinnamoyl-(->6)]-b-D-glucopyranoside] 5-O-(6-O-malonyl-b-D-glucopyranoside))