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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2017-09-18 00:40:58 UTC

Update Date

2023-02-21 17:32:55 UTC

HMDB ID

HMDB0133970

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-Methoxy-1,3-benzenediol

Description

2-Methoxy-1,3-benzenediol, also known as 2-methoxyresorcinol or 2-O-methylpyrogallol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 2-Methoxy-1,3-benzenediol is an extremely weak basic (essentially neutral) compound (based on its pKa). BioTransformer predicts that 2-methoxy-1,3-benzenediol is a product of 1-(2,4-dihydroxy-3-methoxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)propan-1-one metabolism via a keto-hydrolysis-pattern5 reaction occurring in human gut microbiota and catalyzed by an unspecified-gutmicro enzyme (PMID: 30612223 ).

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-O-Methylpyrogallol	MeSH
2-OMPY	MeSH
1,3-Dihydroxy-2-methoxybenzene	HMDB
2,6-Dihydroxyanisole	HMDB
2-Methoxy-1,3-benzenediol	HMDB
2-Methoxybenzene-1,3-diol	HMDB
2-Methoxyresorcinol	HMDB
Pyrogallol-2-methyl ether	HMDB

Chemical Formula

C₇H₈O₃

Average Molecular Weight

140.138

Monoisotopic Molecular Weight

140.047344118

IUPAC Name

2-methoxybenzene-1,3-diol

Traditional Name

2-methoxybenzene-1,3-diol

CAS Registry Number

29267-67-2

SMILES

COC1=C(O)C=CC=C1O

InChI Identifier

InChI=1S/C7H8O3/c1-10-7-5(8)3-2-4-6(7)9/h2-4,8-9H,1H3

InChI Key

QFYYAIBEHOEZKC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Methoxybenzene
Resorcinol
Phenol ether
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7214714)

Excreta

Biofluid or Excreta

Urine (PMID: 7214714)

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	0.54	ALOGPS
logP	1.21	ChemAxon
logS	-0.4	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.48 m³·mol⁻¹	ChemAxon
Polarizability	13.52 Å³	ChemAxon
Number of Rings	1	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
DarkChem	[M+H]+	129.063	31661259
DarkChem	[M-H]-	125.843	31661259
DeepCCS	[M+H]+	130.996	30932474
DeepCCS	[M-H]-	128.608	30932474
DeepCCS	[M-2H]-	165.125	30932474
DeepCCS	[M+Na]+	139.923	30932474
AllCCS	[M+H]+	129.7	32859911
AllCCS	[M+H-H2O]+	125.1	32859911
AllCCS	[M+NH4]+	134.1	32859911
AllCCS	[M+Na]+	135.3	32859911
AllCCS	[M-H]-	124.7	32859911
AllCCS	[M+Na-2H]-	126.4	32859911
AllCCS	[M+HCOO]-	128.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxy-1,3-benzenediol	COC1=C(O)C=CC=C1O	2479.2	Standard polar	33892256
2-Methoxy-1,3-benzenediol	COC1=C(O)C=CC=C1O	1284.2	Standard non polar	33892256
2-Methoxy-1,3-benzenediol	COC1=C(O)C=CC=C1O	1192.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxy-1,3-benzenediol,1TMS,isomer #1	COC1=C(O)C=CC=C1O[Si](C)(C)C	1343.6	Semi standard non polar	33892256
2-Methoxy-1,3-benzenediol,2TMS,isomer #1	COC1=C(O[Si](C)(C)C)C=CC=C1O[Si](C)(C)C	1400.8	Semi standard non polar	33892256
2-Methoxy-1,3-benzenediol,1TBDMS,isomer #1	COC1=C(O)C=CC=C1O[Si](C)(C)C(C)(C)C	1613.8	Semi standard non polar	33892256
2-Methoxy-1,3-benzenediol,2TBDMS,isomer #1	COC1=C(O[Si](C)(C)C(C)(C)C)C=CC=C1O[Si](C)(C)C(C)(C)C	1915.9	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 - 2-Methoxy-1,3-benzenediol GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-7790000000-b1ded4c1fd3119b4e60b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-1,3-benzenediol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-4900000000-071723c54a7a10867e3f	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxy-1,3-benzenediol 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-Methoxy-1,3-benzenediol 10V, Positive-QTOF	splash10-0006-0900000000-38b9aa83eb46942f5352	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-1,3-benzenediol 20V, Positive-QTOF	splash10-0006-0900000000-a20cf776339f079da5ba	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-1,3-benzenediol 40V, Positive-QTOF	splash10-014i-9200000000-1f9867d2135783c592af	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-1,3-benzenediol 10V, Negative-QTOF	splash10-000i-0900000000-f0b92ae95f80b28ef581	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-1,3-benzenediol 20V, Negative-QTOF	splash10-000i-0900000000-332df68f70efafb722e5	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-1,3-benzenediol 40V, Negative-QTOF	splash10-01bd-9100000000-676e6be04c6d3bd6454a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-1,3-benzenediol 10V, Negative-QTOF	splash10-000i-0900000000-eec81e633768bd73c527	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-1,3-benzenediol 20V, Negative-QTOF	splash10-000i-1900000000-7d44405d7247de8ffa7b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-1,3-benzenediol 40V, Negative-QTOF	splash10-014l-9000000000-80777c3cbae2a23f73d0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-1,3-benzenediol 10V, Positive-QTOF	splash10-0006-0900000000-456a7a1716ddd3ed86c8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-1,3-benzenediol 20V, Positive-QTOF	splash10-01oy-9500000000-d902c5dee58891842f22	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxy-1,3-benzenediol 40V, Positive-QTOF	splash10-0f79-9000000000-12852a9d6eea5ffb0473	2021-09-24	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

Not Available

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 and Quantified	0.73 +/- 0.57 umol/mmol creatinine	Not Specified	Not Specified	Normal	7214714	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.14 +/- 0.58 uM	Not Specified	Not Specified	Chronic renal failure	7214714	details

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

FDB090994

KNApSAcK ID

Not Available

Chemspider ID

108676

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

121805

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

Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

Showing metabocard for 2-Methoxy-1,3-benzenediol (HMDB0133970)

MOL for HMDB0133970 (2-Methoxy-1,3-benzenediol)

3D MOL for HMDB0133970 (2-Methoxy-1,3-benzenediol)

3D SDF for HMDB0133970 (2-Methoxy-1,3-benzenediol)

3D-SDF for HMDB0133970 (2-Methoxy-1,3-benzenediol)

PDB for HMDB0133970 (2-Methoxy-1,3-benzenediol)

3D PDB for HMDB0133970 (2-Methoxy-1,3-benzenediol)

SMILES for HMDB0133970 (2-Methoxy-1,3-benzenediol)

INCHI for HMDB0133970 (2-Methoxy-1,3-benzenediol)

Structure for HMDB0133970 (2-Methoxy-1,3-benzenediol)

3D Structure for HMDB0133970 (2-Methoxy-1,3-benzenediol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra