Showing Compound 6''-O-Acetylgenistin (FDB000669)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:40 UTC

Update date

2020-02-24 19:10:11 UTC

Primary ID

FDB000669

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

6''-O-Acetylgenistin

Description

6''-O-Acetylgenistin belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. 6''-O-Acetylgenistin is found, on average, in the highest concentration within a few different foods, such as soy beans (Glycine max), yogurt, and soy yogurt and in a lower concentration in tofu, other soy product, and soy milk. 6''-O-Acetylgenistin has also been detected, but not quantified in, pulses and soy sauce. This could make 6''-O-acetylgenistin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 6''-O-Acetylgenistin.

CAS Number

73566-30-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
(3,4,5-Trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetic acid	Generator
6"-O-acetylgenistin	HMDB
6"-O-Acetylgenistin	biospider
6''-O-Acetylgenistin	db_source
6'-O-Acetylgenistin	HMDB
6-O-Acetylgenistin	HMDB
6-o-acetylgenistin	biospider
Genistin 6''-O-acetate	HMDB

Showing 1 to 8 of 8 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.48 g/L	ALOGPS
logP	1.25	ALOGPS
logP	1.25	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.98 m³·mol⁻¹	ChemAxon
Polarizability	46.22 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C23H22O11

IUPAC name

(3,4,5-trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetate

InChI Identifier

InChI=1S/C23H22O11/c1-10(24)31-9-17-20(28)21(29)22(30)23(34-17)33-13-6-15(26)18-16(7-13)32-8-14(19(18)27)11-2-4-12(25)5-3-11/h2-8,17,20-23,25-26,28-30H,9H2,1H3

InChI Key

DXWGBJJLEDQBKS-UHFFFAOYSA-N

Isomeric SMILES

CC(=O)OCC1OC(OC2=CC(O)=C3C(OC=C(C3=O)C3=CC=C(O)C=C3)=C2)C(O)C(O)C1O

Average Molecular Weight

474.418

Monoisotopic Molecular Weight

474.116211528

Classification

Description

Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavonoid O-glycosides

Direct Parent

Isoflavonoid O-glycosides

Alternative Parents

Substituents

Isoflavonoid o-glycoside
Isoflavonoid-7-o-glycoside
Isoflavone
Hydroxyisoflavonoid
Phenolic glycoside
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Pyran
Monocyclic benzene moiety
Oxane
Benzenoid
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Polyol
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Cytoplasm

Cell and elements:

Extracellular

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 58.23%; H 4.67%; O 37.10%	DFC
Melting Point	Mp 185-186°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	6''-O-Acetylgenistin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-7420900000-399a71205fed850564ae	Spectrum
Predicted GC-MS	6''-O-Acetylgenistin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00b9-3011109000-ddbd2141b60ef4377b38	Spectrum
Predicted GC-MS	6''-O-Acetylgenistin, non-derivatized, 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-1090800000-10a4e5d5b1465d78b93f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0090100000-d77e656717aa9832caaf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-3290000000-7607b39523fdee892d23	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0avi-9140600000-74df749bf00668a5fd31	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-9070100000-53ea2181f3aac4092c1e	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-066r-7190000000-6f1261b04e21d9e7afd4	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-1060900000-ec3adce1103d1249e654	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-066r-4092400000-4a834e497df60e75124e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-016r-2290000000-52035863609d1d03d5c3	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090400000-05977e9145fe41440509	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0090000000-aefaeb48a9aa9d9d22e3	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-7391200000-d7c197fc117eedacf521	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

11317869

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

22288010

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

405

DrugBank ID

Not Available

HMDB ID

HMDB29528

CRC / DFC (Dictionary of Food Compounds) ID

GZR02-N:BFL71-Q

EAFUS ID

Not Available

Dr. Duke ID

6"-O-ACETYL-GENISTIN

BIGG ID

Not Available

KNApSAcK ID

C00010104

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

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Descriptor	ID	Definition	Reference
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE

Showing 1 to 1 of 1 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available