Showing Compound Isoferreirin (FDB000623)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:39 UTC

Update date

2020-02-24 19:10:10 UTC

Primary ID

FDB000623

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Isoferreirin

Description

Isoferreirin belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, isoferreirin is considered to be a flavonoid. Isoferreirin has been detected, but not quantified in, a few different foods, such as fruits, lima beans (Phaseolus lunatus), and scarlet beans (Phaseolus coccineus). This could make isoferreirin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isoferreirin.

CAS Number

76656-75-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.57	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.14 m³·mol⁻¹	ChemAxon
Polarizability	29.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H14O6

IUPAC name

5,7-dihydroxy-3-(4-hydroxy-2-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

InChI Identifier

InChI=1S/C16H14O6/c1-21-13-5-8(17)2-3-10(13)11-7-22-14-6-9(18)4-12(19)15(14)16(11)20/h2-6,11,17-19H,7H2,1H3

InChI Key

VODZWHSRITUHNI-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(C=CC(O)=C1)C1COC2=CC(O)=CC(O)=C2C1=O

Average Molecular Weight

302.2788

Monoisotopic Molecular Weight

302.07903818

Classification

Description

Belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

2'-O-methylated isoflavonoids

Alternative Parents

Substituents

2p-methoxyisoflavonoid-skeleton
Isoflavanol
Isoflavanone
Hydroxyisoflavonoid
Isoflavan
Chromone
Methoxyphenol
Benzopyran
1-benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Phenol ether
Phenoxy compound
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050503 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Fabaceae

Biological location:

Subcellular:

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 63.57%; H 4.67%; O 31.76%	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	Isoferreirin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dr-0971000000-ee5cfcd61d28041e466d	Spectrum
Predicted GC-MS	Isoferreirin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0w91-2690650000-8eb3972531ebbafa81ac	Spectrum
Predicted GC-MS	Isoferreirin, 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	splash10-0udi-0439000000-f935d68f92181bd84126	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0933000000-938eb046c9246d8aa0c1	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-3900000000-ee2398fb409ee73b3722	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0019000000-0af4c2ca8b44a15cefc2	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1869000000-40a81608780e20d6184a	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9620000000-043ccee68ed8858c4c71	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-d1450f45777bb06cb577	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0913000000-1f7abd1a9624c3d18ceb	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvr-1910000000-c1cecbeac21c534c018a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0309000000-dcc4dcfe1b2a36efa446	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fba-0792000000-db2f5160872db93bc93a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6t-1590000000-81c11f258adfbbf0cb3f	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

137998

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

156743

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB29491

CRC / DFC (Dictionary of Food Compounds) ID

FMC58-N:BFF23-Z

EAFUS ID

Not Available

Dr. Duke ID

ISOFERREIRIN

BIGG ID

Not Available

KNApSAcK ID

C00009554

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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Search:

Food	Content Range	Average	Reference

Lima bean	Expected but not quantified	Not Available	DUKE
Scarlet bean	Expected but not quantified	Not Available	DUKE, KNAPSACK

Showing 1 to 2 of 2 entries

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

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Showing Compound Isoferreirin (FDB000623)

Structure for FDB000623 (Isoferreirin)