Showing Compound (R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (FDB017266)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:59 UTC

Update date

2019-11-26 03:14:34 UTC

Primary ID

FDB017266

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one

Description

2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. 2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one has been detected, but not quantified in, several different foods, such as wheats (Triticum), rice (Oryza sativa), red rice (Oryza rufipogon), coffee and coffee products, and quinoas (Chenopodium quinoa). This could make 2-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one.

CAS Number

17359-53-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one	manual
2-Hydroxy-7-methoxy-1,4-benzoxazin-3-one	HMDB
2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one	db_source
2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3-one	HMDB, MeSH
2H-1,4-Benzoxazin-3(4H)-one, 2-hydroxy-7-methoxy-	biospider
Hmboa	HMDB
HMBOA	biospider

Showing 1 to 7 of 7 entries

Predicted Properties

Property	Value	Source
Water Solubility	19.9 g/L	ALOGPS
logP	0.42	ALOGPS
logP	0.31	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	10.06	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.79 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.49 m³·mol⁻¹	ChemAxon
Polarizability	18.39 Å³	ChemAxon
Number of Rings	2	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

C9H9NO4

IUPAC name

2-hydroxy-7-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

InChI Identifier

InChI=1S/C9H9NO4/c1-13-5-2-3-6-7(4-5)14-9(12)8(11)10-6/h2-4,9,12H,1H3,(H,10,11)

InChI Key

NDEPTLCFICMYLH-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC2=C(NC(=O)C(O)O2)C=C1

Average Molecular Weight

195.1721

Monoisotopic Molecular Weight

195.053157781

Classification

Description

Belongs to the class of organic compounds known as benzoxazinones. These are organic compounds containing a benzene fused to an oxazine ring (a six-member aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazines

Sub Class

Benzoxazinones

Direct Parent

Benzoxazinones

Alternative Parents

Substituents

Benzoxazinone
Benzomorpholine
Anisole
Alkyl aryl ether
Benzenoid
Oxazinane
Carboxamide group
Secondary carboxylic acid amide
Lactam
Hemiacetal
Oxacycle
Azacycle
Carboxylic acid derivative
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-6404 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Foods

Grains:

Cereal products:

Whole grain cereal products

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 55.39%; H 4.65%; N 7.18%; O 32.79%	DFC
Melting Point	Mp 198-199.5°	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	(R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01bi-0900000000-d552a07ba9aa1f9128c0	Spectrum
Predicted GC-MS	(R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0079-9820000000-3397e1dc337c31dde218	Spectrum
Predicted GC-MS	(R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, 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	splash10-0002-0900000000-8822f5739ba8a8ddba2f	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mk-2900000000-4b4d0fb87ad91d846a84	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w29-6900000000-a439083b905512efd8db	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0005-0900000000-56596824f268d394016e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-494a7840dc2e0b15783a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-ffd188728d66109a94ad	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-a5577174dafb39a02fc7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-2633be04faf9af00f592	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-4900000000-bfba9343249386a1f9dc	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-9ffb082263d8775df21f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-66c1ceb017c05edf5e06	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05g3-4900000000-3291bcaa3e1d54e5310e	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

134162

ChEMBL ID

CHEMBL451316

KEGG Compound ID

Not Available

Pubchem Compound ID

152213

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB38055

CRC / DFC (Dictionary of Food Compounds) ID

KWX32-X:KWX34-Z

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 (R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (FDB017266)

Structure for FDB017266 ((R)-2-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one)