Showing Compound Proanthocyanidin A5' 3-galactoside (FDB019520)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:24 UTC

Update date

2019-11-26 03:17:34 UTC

Primary ID

FDB019520

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Proanthocyanidin A5' 3-galactoside

Description

3-O-beta-D-Galactopyranosylproanthocyanidin A5' belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. 3-O-beta-D-Galactopyranosylproanthocyanidin A5' has been detected, but not quantified in, cocoa and cocoa products and cocoa beans (Theobroma cacao). This could make 3-O-beta-D-galactopyranosylproanthocyanidin a5' a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-O-beta-D-Galactopyranosylproanthocyanidin A5'.

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
3-O-b-D-Galactopyranosylproanthocyanidin a5'	Generator
3-O-b-D-Galactopyranosylproanthocyanidin A5'	db_source
3-O-Β-D-galactopyranosylproanthocyanidin a5'	Generator
Proanthocyanidin A5' 3-galactoside	manual

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.82	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	288.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	176.61 m³·mol⁻¹	ChemAxon
Polarizability	71.05 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C36H34O17

IUPAC name

5,13-bis(3,4-dihydroxyphenyl)-21-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2,8,10,15,17,19-hexaene-6,9,17,19-tetrol

InChI Identifier

InChI=1S/C36H34O17/c37-11-25-29(46)30(47)31(48)35(49-25)51-34-28-26-21(44)7-14(38)8-23(26)52-36(34,13-2-4-17(40)20(43)6-13)53-24-10-18(41)15-9-22(45)32(50-33(15)27(24)28)12-1-3-16(39)19(42)5-12/h1-8,10,22,25,28-32,34-35,37-48H,9,11H2

InChI Key

JUIIUJBWZYKSEP-UHFFFAOYSA-N

Isomeric SMILES

OCC1OC(OC2C3C4=C(O)C=C(O)C=C4OC2(OC2=CC(O)=C4CC(O)C(OC4=C32)C2=CC=C(O)C(O)=C2)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O

Average Molecular Weight

738.645

Monoisotopic Molecular Weight

738.179599662

Classification

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

A-type proanthocyanidin
Proanthocyanidin
Bi- and polyflavonoid skeleton
Catechin
Pyranoflavonoid
Hydroxyflavonoid
3'-hydroxyflavonoid
3-hydroxyflavonoid
Flavan-3-ol
4'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
Flavan
Pyranochromene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromane
Benzopyran
1-benzopyran
Catechol
Phenol
Ketal
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Organooxygen compound
Primary alcohol
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Theobroma cacao

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 58.54%; H 4.64%; O 36.82%	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	Proanthocyanidin A5' 3-galactoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0kmi-7900012700-f44727241d7e13baa403	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_1_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Proanthocyanidin A5' 3-galactoside, TMS_2_12, 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	splash10-05dr-0200190600-97706664d5aeea34bf2c	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0300590100-60d6fcf00696e0cd0675	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-1912820100-f1a3b8bc2fd3ce81fbb6	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-1310061900-3c9fef71e9696d7e9849	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1800191200-389652470c629f0c6f66	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-6961540000-20666cf2d2b17312d439	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a70-0000090500-1cb03dcde7b8e53ce4ff	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004r-0300138900-fa4330e94f076d7adbcb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0570-8400249100-27e54ad5a9cb8268e401	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000900-22b79d63ee65107e7762	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1200142900-87dae263d40ffcc78c30	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-2300490000-3d0778520dc02bc1979a	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

HMDB39862

CRC / DFC (Dictionary of Food Compounds) ID

KTF42-T:MBQ39-A

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 Proanthocyanidin A5' 3-galactoside (FDB019520)

Structure for FDB019520 (Proanthocyanidin A5' 3-galactoside)