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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 23:05:03 UTC

Update Date

2021-09-23 23:05:03 UTC

HMDB ID

HMDB0303071

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2H-1,4-Benzoxazin-3(4H)-one

Description

2h-1,4-benzoxazin-3(4h)-one is a member of the class of compounds known as benzoxazinones. Benzoxazinones 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. 2h-1,4-benzoxazin-3(4h)-one is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 2h-1,4-benzoxazin-3(4h)-one can be found in corn, which makes 2h-1,4-benzoxazin-3(4h)-one a potential biomarker for the consumption of this food product.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₈H₇NO₂

Average Molecular Weight

149.1467

Monoisotopic Molecular Weight

149.047678473

IUPAC Name

3,4-dihydro-2H-1,4-benzoxazin-3-one

Traditional Name

2H-1,4-benzoxazin-3(4H)-one

CAS Registry Number

Not Available

SMILES

O=C1COC2=C(N1)C=CC=C2

InChI Identifier

InChI=1S/C8H7NO2/c10-8-5-11-7-4-2-1-3-6(7)9-8/h1-4H,5H2,(H,9,10)

InChI Key

QRCGFTXRXYMJOS-UHFFFAOYSA-N

Chemical Taxonomy

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-6405 )

Ontology

Not Available

Exogenous (HMDB: HMDB0303071)

Food

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.76	ALOGPS
logP	0.75	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.63	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.83 m³·mol⁻¹	ChemAxon
Polarizability	14.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	131.263	32859911
AllCCS	[M+H-H2O]+	126.546	32859911
AllCCS	[M+Na]+	136.934	32859911
AllCCS	[M+NH4]+	135.664	32859911
AllCCS	[M-H]-	129.353	32859911
AllCCS	[M+Na-2H]-	130.261	32859911
AllCCS	[M+HCOO]-	131.318	32859911
DeepCCS	[M+H]+	131.668	30932474
DeepCCS	[M-H]-	128.177	30932474
DeepCCS	[M-2H]-	165.608	30932474
DeepCCS	[M+Na]+	140.819	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.7838 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.78 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1529.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	362.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	119.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	225.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	92.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	346.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	509.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	850.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	250.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1049.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	298.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	429.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	235.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	112.6 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2H-1,4-Benzoxazin-3(4H)-one,1TMS,isomer #1	C[Si](C)(C)N1C(=O)COC2=CC=CC=C21	1495.8	Semi standard non polar	33892256
2H-1,4-Benzoxazin-3(4H)-one,1TMS,isomer #1	C[Si](C)(C)N1C(=O)COC2=CC=CC=C21	1523.5	Standard non polar	33892256
2H-1,4-Benzoxazin-3(4H)-one,1TMS,isomer #1	C[Si](C)(C)N1C(=O)COC2=CC=CC=C21	2128.3	Standard polar	33892256
2H-1,4-Benzoxazin-3(4H)-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)COC2=CC=CC=C21	1729.7	Semi standard non polar	33892256
2H-1,4-Benzoxazin-3(4H)-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)COC2=CC=CC=C21	1771.1	Standard non polar	33892256
2H-1,4-Benzoxazin-3(4H)-one,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)COC2=CC=CC=C21	2258.5	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 10V, Positive-QTOF	splash10-0udi-0900000000-a2d6f9967c37740fb193	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 20V, Positive-QTOF	splash10-0udi-1900000000-fbdb51edf5cc934181e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 40V, Positive-QTOF	splash10-0udl-9800000000-08bb93dcd92098e4a4d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 10V, Negative-QTOF	splash10-0002-0900000000-66ddfc6f5a38466cb23c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 20V, Negative-QTOF	splash10-0002-0900000000-e6dd750ba08e2ca256de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 40V, Negative-QTOF	splash10-014i-6900000000-4333d7617710a075f27e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 10V, Positive-QTOF	splash10-0udi-0900000000-e9c84d792f3855d1e622	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 20V, Positive-QTOF	splash10-0zfr-0900000000-ba5ab36e5a643b97e969	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 40V, Positive-QTOF	splash10-0fai-9100000000-ea308a0a757b52be5da8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 10V, Negative-QTOF	splash10-0002-0900000000-d32a0a3b410ab4200586	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 20V, Negative-QTOF	splash10-0002-3900000000-029f336a55e8224fb200	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2H-1,4-Benzoxazin-3(4H)-one 40V, Negative-QTOF	splash10-0006-9500000000-0bcf62ecd9792cd9cc94	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007622

KNApSAcK ID

C00026498

Chemspider ID

65595

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72757

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 2H-1,4-Benzoxazin-3(4H)-one (HMDB0303071)

MOL for HMDB0303071 (2H-1,4-Benzoxazin-3(4H)-one)

3D MOL for HMDB0303071 (2H-1,4-Benzoxazin-3(4H)-one)

3D SDF for HMDB0303071 (2H-1,4-Benzoxazin-3(4H)-one)

3D-SDF for HMDB0303071 (2H-1,4-Benzoxazin-3(4H)-one)

PDB for HMDB0303071 (2H-1,4-Benzoxazin-3(4H)-one)

3D PDB for HMDB0303071 (2H-1,4-Benzoxazin-3(4H)-one)

SMILES for HMDB0303071 (2H-1,4-Benzoxazin-3(4H)-one)

INCHI for HMDB0303071 (2H-1,4-Benzoxazin-3(4H)-one)

Structure for HMDB0303071 (2H-1,4-Benzoxazin-3(4H)-one)

3D Structure for HMDB0303071 (2H-1,4-Benzoxazin-3(4H)-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra