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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:52:44 UTC

Update Date

2023-02-21 17:22:48 UTC

HMDB ID

HMDB0032931

Secondary Accession Numbers

HMDB32931

Metabolite Identification

Common Name

2-Benzoxazolol

Description

2-Benzoxazolol, also known as benzoxazolinone, belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. 2-Benzoxazolol has been detected, but not quantified in, several different foods, such as tartary buckwheats (Fagopyrum tataricum), hard wheats (Triticum durum), sorghums (Sorghum bicolor), bulgur, and cereals and cereal products. This could make 2-benzoxazolol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Benzoxazolol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3H)-1,3-Benzoxazol-2-one	ChEBI
2(3H)-Benzoxazolone	ChEBI
2,3-Dihydro-2-oxo-1,3-benzoxazole	ChEBI
Benzoxazolin-2(3H)-one	ChEBI
Benzoxazolin-2-one	ChEBI
Benzoxazolinone	ChEBI
Benzoxazolone	ChEBI
benzo[D]Oxazol-2(3H)-one	ChEMBL, HMDB
1,3-Benzoxazol-2(3H)-one	HMDB
2(3H)-Benzoxazolinone	HMDB
2(3H)-Benzoxazolone, 9ci	HMDB
2-Benzoxaxolol	HMDB
2-Benzoxazolinone, 8ci	HMDB
2-Benzoxazolone	HMDB
2-Hydroxy-benzoxazole	HMDB
2-Hydroxybenzoxazole	HMDB
3H-Benzooxazol-2-one	HMDB
Carbamic acid, (2-hydroxyphenyl)-, gamma-lactone	HMDB
Benzoxalinone	MeSH
Benzoxazolone-2	MeSH
2-Benzoxazolinone	MeSH
Benzoxazolone zinc salt	MeSH

Chemical Formula

C₇H₅NO₂

Average Molecular Weight

135.1201

Monoisotopic Molecular Weight

135.032028409

IUPAC Name

2,3-dihydro-1,3-benzoxazol-2-one

Traditional Name

O-phenylene carbamate

CAS Registry Number

59-49-4

SMILES

O=C1NC2=CC=CC=C2O1

InChI Identifier

InChI=1S/C7H5NO2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)

InChI Key

ASSKVPFEZFQQNQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxazoles

Sub Class

Benzoxazolones

Direct Parent

Benzoxazolones

Alternative Parents

Substituents

Benzoxazolone
Benzenoid
Heteroaromatic compound
Oxazole
Azole
Oxacycle
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Cellular substructure

Extracellular (HMDB: HMDB0032931)
Cytoplasm (HMDB: HMDB0032931)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032931)

Source

Exogenous

Exogenous (HMDB: HMDB0032931)

Food

Food (HMDB: HMDB0032931)

Cereal and cereal product

Cereal

Cereal product

Breakfast cereal (FooDB: FOOD00270)
Whole grain cereal products (HMDB: HMDB0032931)
Flour (FooDB: FOOD00799)
Bulgur (FooDB: FOOD00741)

Cereals and cereal products (FooDB: FOOD00858)

Soy

Soy bean (FooDB: FOOD00085)

Herb and spice

Herb

Amaranth (FooDB: FOOD00288)
Teff (FooDB: FOOD00489)

Other seed

Quinoa (FooDB: FOOD00441)

Endogenous

Plant

Poaceae (HMDB: HMDB0032931)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032931)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	141 - 142 °C	Not Available
Boiling Point	335.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	8962 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.16	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	16.2 g/L	ALOGPS
logP	0.95	ALOGPS
logP	1.33	ChemAxon
logS	-0.92	ALOGPS
pKa (Strongest Acidic)	9.48	ChemAxon
pKa (Strongest Basic)	-2	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	36.26 m³·mol⁻¹	ChemAxon
Polarizability	12.64 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
DarkChem	[M+H]+	125.949	31661259
DarkChem	[M-H]-	123.197	31661259
DeepCCS	[M+H]+	124.956	30932474
DeepCCS	[M-H]-	122.222	30932474
DeepCCS	[M-2H]-	158.909	30932474
DeepCCS	[M+Na]+	133.744	30932474
AllCCS	[M+H]+	126.8	32859911
AllCCS	[M+H-H2O]+	122.0	32859911
AllCCS	[M+NH4]+	131.4	32859911
AllCCS	[M+Na]+	132.7	32859911
AllCCS	[M-H]-	122.4	32859911
AllCCS	[M+Na-2H]-	123.5	32859911
AllCCS	[M+HCOO]-	124.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.65 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3287 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.18 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1530.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	426.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	161.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	289.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	286.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	363.7 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	470.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	175.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	961.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	347.8 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	1045.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	355.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	296.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	442.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	280.9 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	93.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Benzoxazolol	O=C1NC2=CC=CC=C2O1	2310.4	Standard polar	33892256
2-Benzoxazolol	O=C1NC2=CC=CC=C2O1	1500.6	Standard non polar	33892256
2-Benzoxazolol	O=C1NC2=CC=CC=C2O1	1526.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Benzoxazolol,1TMS,isomer #1	C[Si](C)(C)N1C(=O)OC2=CC=CC=C21	1514.3	Semi standard non polar	33892256
2-Benzoxazolol,1TMS,isomer #1	C[Si](C)(C)N1C(=O)OC2=CC=CC=C21	1526.7	Standard non polar	33892256
2-Benzoxazolol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)OC2=CC=CC=C21	1725.6	Semi standard non polar	33892256
2-Benzoxazolol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C(=O)OC2=CC=CC=C21	1742.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Benzoxazolol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-2900000000-53a6e6944c216f2ff450	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Benzoxazolol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 10V, Positive-QTOF	splash10-000i-0900000000-28cb5d5dabfbd4444d16	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 20V, Positive-QTOF	splash10-000i-1900000000-68360d67f7e58d4e47ce	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 40V, Positive-QTOF	splash10-0006-9000000000-3ef23435b09f8a06712b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 10V, Negative-QTOF	splash10-001i-0900000000-6470f4530d4a76a20c87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 20V, Negative-QTOF	splash10-001i-0900000000-2b15491c747ad923c14b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 40V, Negative-QTOF	splash10-0006-9000000000-47c3f0d3c33c155d00d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 10V, Negative-QTOF	splash10-001i-0900000000-dfaff11718b97e70ed95	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 20V, Negative-QTOF	splash10-053r-0900000000-efbd7e2e5f22a71e7a7e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 40V, Negative-QTOF	splash10-0a59-1900000000-92ff3f1b4473100dd6bb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 10V, Positive-QTOF	splash10-052r-0900000000-5745440511be52fb47fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 20V, Positive-QTOF	splash10-000i-0900000000-2a9c164d4c68d91f9133	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Benzoxazolol 40V, Positive-QTOF	splash10-053r-9300000000-7116d2292c1e693cf11b	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

FDB010916

KNApSAcK ID

C00028319

Chemspider ID

5820

KEGG Compound ID

Not Available

BioCyc ID

CPD-19393

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6043

PDB ID

Not Available

ChEBI ID

145233

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1171341

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 2-Benzoxazolol (HMDB0032931)

MOL for HMDB0032931 (2-Benzoxazolol)

3D MOL for HMDB0032931 (2-Benzoxazolol)

3D SDF for HMDB0032931 (2-Benzoxazolol)

3D-SDF for HMDB0032931 (2-Benzoxazolol)

PDB for HMDB0032931 (2-Benzoxazolol)

3D PDB for HMDB0032931 (2-Benzoxazolol)

SMILES for HMDB0032931 (2-Benzoxazolol)

INCHI for HMDB0032931 (2-Benzoxazolol)

Structure for HMDB0032931 (2-Benzoxazolol)

3D Structure for HMDB0032931 (2-Benzoxazolol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra