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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:46:27 UTC

Update Date

2021-09-26 22:54:20 UTC

HMDB ID

HMDB0245720

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Hydroxybenzofuran-2(3H)-one

Description

5-Hydroxybenzofuran-2(3H)-one, also known as 5-hydroxy-2(3H)-benzofuranone or homogentisic acid gamma-lactone, belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 5-Hydroxybenzofuran-2(3H)-one is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on 5-Hydroxybenzofuran-2(3H)-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-hydroxybenzofuran-2(3h)-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-Hydroxybenzofuran-2(3H)-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3-Dihydro-5-hydroxybenzofuran-2-one	ChEBI
5-Hydroxy-2(3H)-benzofuranone	ChEBI
5-Hydroxy-2-coumaranone	ChEBI
Homogentisic acid gamma-lactone	ChEBI
Homogentisate g-lactone	Generator
Homogentisate gamma-lactone	Generator
Homogentisate γ-lactone	Generator
Homogentisic acid g-lactone	Generator
Homogentisic acid γ-lactone	Generator

Chemical Formula

C₈H₆O₃

Average Molecular Weight

150.133

Monoisotopic Molecular Weight

150.031694053

IUPAC Name

5-hydroxy-2,3-dihydro-1-benzofuran-2-one

Traditional Name

5-hydroxy-3H-1-benzofuran-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(OC(=O)C2)C=C1

InChI Identifier

InChI=1S/C8H6O3/c9-6-1-2-7-5(3-6)4-8(10)11-7/h1-3,9H,4H2

InChI Key

POUITAHNNRJWMA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Coumaran
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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: 31557052)

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	1.08	ALOGPS
logP	1.14	ChemAxon
logS	-0.94	ALOGPS
pKa (Strongest Acidic)	9.38	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	37.84 m³·mol⁻¹	ChemAxon
Polarizability	14.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	129.561	30932474
DeepCCS	[M-H]-	126.65	30932474
DeepCCS	[M-2H]-	163.613	30932474
DeepCCS	[M+Na]+	139.023	30932474
AllCCS	[M+H]+	130.6	32859911
AllCCS	[M+H-H2O]+	125.8	32859911
AllCCS	[M+NH4]+	135.0	32859911
AllCCS	[M+Na]+	136.2	32859911
AllCCS	[M-H]-	127.6	32859911
AllCCS	[M+Na-2H]-	128.4	32859911
AllCCS	[M+HCOO]-	129.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxybenzofuran-2(3H)-one	OC1=CC2=C(OC(=O)C2)C=C1	2935.1	Standard polar	33892256
5-Hydroxybenzofuran-2(3H)-one	OC1=CC2=C(OC(=O)C2)C=C1	1526.1	Standard non polar	33892256
5-Hydroxybenzofuran-2(3H)-one	OC1=CC2=C(OC(=O)C2)C=C1	1633.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxybenzofuran-2(3H)-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zmi-1900000000-4c4ed7ef1b5d90b16bf4	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxybenzofuran-2(3H)-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxybenzofuran-2(3H)-one GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxybenzofuran-2(3H)-one GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - 5-Hydroxybenzofuran-2(3H)-one 10V, Positive-QTOF	splash10-0udi-0900000000-84ccb831556a0a7481f6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxybenzofuran-2(3H)-one 20V, Positive-QTOF	splash10-0udi-0900000000-182e193f9390f954e86e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxybenzofuran-2(3H)-one 40V, Positive-QTOF	splash10-0aor-9400000000-a0b8664d63d361ae1bb4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxybenzofuran-2(3H)-one 10V, Negative-QTOF	splash10-0002-0900000000-17a70aedff451f61a5cf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxybenzofuran-2(3H)-one 20V, Negative-QTOF	splash10-0002-2900000000-6aaf39ab6b9b5551f351	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxybenzofuran-2(3H)-one 40V, Negative-QTOF	splash10-00r6-9200000000-35dfb703e368b575035d	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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	Not Specified	Not Specified	Normal	31557052	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

68403

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75898

PDB ID

Not Available

ChEBI ID

141343

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 5-Hydroxybenzofuran-2(3H)-one (HMDB0245720)

MOL for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

3D MOL for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

3D SDF for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

3D-SDF for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

PDB for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

3D PDB for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

SMILES for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

INCHI for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

Structure for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

3D Structure for HMDB0245720 (5-Hydroxybenzofuran-2(3H)-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra