Showing Compound Genistein 7-O-(2-p-coumaroylglucoside) (FDB018152)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:32 UTC

Update date

2019-11-26 03:15:46 UTC

Primary ID

FDB018152

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Genistein 7-O-(2-p-coumaroylglucoside)

Description

Genistein 7-O-(2-p-coumaroylglucoside) 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. Genistein 7-O-(2-p-coumaroylglucoside) has been detected, but not quantified in, several different foods, such as red tea, green vegetables, herbal tea, herbs and spices, and teas (Camellia sinensis). This could make genistein 7-O-(2-p-coumaroylglucoside) a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Genistein 7-O-(2-p-coumaroylglucoside).

CAS Number

106915-84-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
4,5-Dihydroxy-2-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoic acid	Generator
Genistein 7-O-(2''-P-coumaroylglucoside)	HMDB
Genistein 7-O-(2''-p-coumaroylglucoside)	biospider
Genistein 7-O-(2-p-coumaroylglucoside)	db_source

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.083 g/L	ALOGPS
logP	2.88	ALOGPS
logP	3.54	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.32	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	145.38 m³·mol⁻¹	ChemAxon
Polarizability	58.44 Å³	ChemAxon
Number of Rings	5	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

C30H26O12

IUPAC name

4,5-dihydroxy-2-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

InChI Identifier

InChI=1S/C30H26O12/c31-13-23-27(37)28(38)29(42-24(35)10-3-15-1-6-17(32)7-2-15)30(41-23)40-19-11-21(34)25-22(12-19)39-14-20(26(25)36)16-4-8-18(33)9-5-16/h1-12,14,23,27-34,37-38H,13H2/b10-3+

InChI Key

NRJJZSQAAJJXTJ-XCVCLJGOSA-N

Isomeric SMILES

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

Average Molecular Weight

578.5202

Monoisotopic Molecular Weight

578.142426296

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-7-o-glycoside
Isoflavonoid o-glycoside
Isoflavone
Hydroxyisoflavonoid
Phenolic glycoside
Coumaric acid ester
Cinnamic acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Chromone
Glycosyl compound
Benzopyran
1-benzopyran
Styrene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Monosaccharide
Pyran
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Alcohol
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 62.28%; H 4.53%; O 33.19%	DFC
Melting Point	Mp 250-252°	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	Genistein 7-O-(2-p-coumaroylglucoside), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xr-9542160000-476248340fae2c8cc3d5	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0g4r-3911103000-e926e82a88b24437ee8c	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), "Genistein 7-O-(2-p-coumaroylglucoside),1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Genistein 7-O-(2-p-coumaroylglucoside), TMS_3_2, 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-0491450000-8ec3b5836fe18655a863	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0290100000-2544de8acdb8f752c704	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-1490000000-ca740238a9bb082f5d26	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0400-1882790000-c272cceb092e166adc60	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02t9-0891210000-6e573a5600fc3b75fcd3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-2960000000-1879899ca53f89c93c46	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0410290000-c449698efd45b0471ae6	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1490220000-a205f86c530871b47597	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0940010000-53dd09f5145e1ab69d29	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0430090000-8cecad194e0305d9d3fc	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0avj-1930140000-6cb66517936e1f70cc2e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-069c-8920030000-9b335b60f0206cb1a6e1	2021-09-25	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

HMDB38741

CRC / DFC (Dictionary of Food Compounds) ID

GZR02-N:LGZ85-C

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00010164

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

Black tea	Expected but not quantified	Not Available	DFC CODES
Green tea	Expected but not quantified	Not Available	DFC CODES
Herbal tea	Expected but not quantified	Not Available	DFC CODES
Red tea	Expected but not quantified	Not Available	DFC CODES