ContaminantDB: (R)-2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 21:00:49 UTC

Update Date

2016-11-09 01:17:42 UTC

Accession Number

CHEM023374

Identification

Common Name

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

Class

Small Molecule

Description

DIMBOA-Glc is found in cereals and cereal products. DIMBOA-Glc is isolated from sweet corn (Zea mays

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-O-Glucopyranosyl-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one	MeSH, HMDB
DIMBOAGlc	MeSH, HMDB
2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-O-glucoside	MeSH, HMDB
DIMBOA-GLC	MeSH

Chemical Formula

C₁₅H₁₉NO₁₀

Average Molecular Mass

373.312 g/mol

Monoisotopic Mass

373.101 g/mol

CAS Registry Number

113565-32-5

IUPAC Name

4-hydroxy-7-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1,4-benzoxazin-3-one

Traditional Name

4-hydroxy-7-methoxy-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-1,4-benzoxazin-3-one

SMILES

COC1=CC2=C(C=C1)N(O)C(=O)C(OC1OC(CO)C(O)C(O)C1O)O2

InChI Identifier

InChI=1S/C15H19NO10/c1-23-6-2-3-7-8(4-6)24-15(13(21)16(7)22)26-14-12(20)11(19)10(18)9(5-17)25-14/h2-4,9-12,14-15,17-20,22H,5H2,1H3

InChI Key

WTGXAWKVZMQEDA-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
Benzoxazinone
O-glycosyl compound
Benzomorpholine
Benzoxazine
Anisole
Alkyl aryl ether
Monosaccharide
Oxane
Oxazinane
Benzenoid
Secondary alcohol
Hydroxamic acid
Oxacycle
Polyol
Azacycle
Organoheterocyclic compound
Acetal
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Alcohol
Organonitrogen compound
Primary alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

an indole derivative (CPD-6562 )
a glucoside (CPD-6562 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	18.4 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.8	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	7.85	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	158.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	80.88 m³·mol⁻¹	ChemAxon
Polarizability	34.72 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-9736000000-04d7b20345ab8972b96a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0002-1411139000-87956e2ec5a4c15086c0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0296-0930000000-b461bf85334f237f5507	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-01ot-0900000000-c1bc5bcd5c4f195afd1c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Negative	splash10-01ot-0900000000-2dd4350d5526c3fad62d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0296-0930000000-832a10f5f2d6abcc449a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0696000000-3bb559699e0fe6824490	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2893000000-a400569db2c68db0f07b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-4910000000-dfa5f0475a55e7e60411	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03k9-2679000000-9c48d0bf15dda702dd9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dl-3943000000-bd70009b2f2b1f6c68ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-9700000000-78221a3de016ab112b5f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0119000000-8e0aeb5138de79e2f4b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0920000000-74700fb9f4a5d925c09b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1921000000-b45661b63e8c62786ad7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dl-0539000000-daf1ac7dc7e03135a09f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-1921000000-365277bf1e6b52a911ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0k9x-3900000000-0454d6a0ce9e52de6fb7	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0029710

FooDB ID

FDB000904

Phenol Explorer ID

Not Available

KNApSAcK ID

C00056489

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

3678276

ChEBI ID

168617

PubChem Compound ID

4480305

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Cicek M, Blanchard D, Bevan DR, Esen A: The aglycone specificity-determining sites are different in 2, 4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA)-glucosidase (Maize beta -glucosidase) and dhurrinase (Sorghum beta -glucosidase). J Biol Chem. 2000 Jun 30;275(26):20002-11.

2. Czjzek M, Cicek M, Zamboni V, Burmeister WP, Bevan DR, Henrissat B, Esen A: Crystal structure of a monocotyledon (maize ZMGlu1) beta-glucosidase and a model of its complex with p-nitrophenyl beta-D-thioglucoside. Biochem J. 2001 Feb 15;354(Pt 1):37-46.

3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

(R)-2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside (CHEM023374)

Structure for CHEM023374: (R)-2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one 2-glucoside