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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-09-13 02:16:00 UTC

Update Date

2023-02-21 17:31:33 UTC

HMDB ID

HMDB0125538

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-methoxybenzene-1,2-diol

Description

3-methoxybenzene-1,2-diol, also known as 1-O-methylpyrogallol or 2,3-dihydroxyanisole, 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. 3-methoxybenzene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Dihydroxy-3-methoxybenzene	ChEBI
1-O-Methylpyrogallol	ChEBI
2,3-Dihydroxyanisole	ChEBI
3-Methoxy-O-hydroquinone	ChEBI
3-Methoxypyrocatechol	ChEBI
6-Methoxycatechol	ChEBI
Pyrogallol 1-methyl ether	ChEBI
Pyrogallol 1-monomethyl ether	ChEBI

Chemical Formula

C₇H₈O₃

Average Molecular Weight

140.138

Monoisotopic Molecular Weight

140.047344118

IUPAC Name

3-methoxybenzene-1,2-diol

Traditional Name

1,2-benzenediol, 3-methoxy-

CAS Registry Number

Not Available

SMILES

COC1=CC=CC(O)=C1O

InChI Identifier

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

InChI Key

LPYUENQFPVNPHY-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
Phenol ether
Catechol
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: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Endogenous

Endogenous (HMDB: HMDB0125538)

Exogenous

Food

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0125538)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0125538)

Tea

Tea products (HMDB: HMDB0125538)

Fat and oil

Olive oil (HMDB: HMDB0125538)

Fruit

Fruits (HMDB: HMDB0125538)

Vegetable

Vegetables (HMDB: HMDB0125538)

Legumes (HMDB: HMDB0125538)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0125538)

Nut

Nuts (HMDB: HMDB0125538)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0125538)

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	124.67	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000900

Predicted Molecular Properties

Property	Value	Source
logP	0.52	ALOGPS
logP	1.21	ChemAxon
logS	-0.47	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	-4.9	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	13.51 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]+	128.69	31661259
DarkChem	[M-H]-	126.493	31661259
DeepCCS	[M+H]+	130.559	30932474
DeepCCS	[M-H]-	127.993	30932474
DeepCCS	[M-2H]-	164.706	30932474
DeepCCS	[M+Na]+	139.474	30932474
AllCCS	[M+H]+	129.8	32859911
AllCCS	[M+H-H2O]+	125.2	32859911
AllCCS	[M+NH4]+	134.2	32859911
AllCCS	[M+Na]+	135.4	32859911
AllCCS	[M-H]-	124.9	32859911
AllCCS	[M+Na-2H]-	126.7	32859911
AllCCS	[M+HCOO]-	128.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-methoxybenzene-1,2-diol	COC1=CC=CC(O)=C1O	2438.7	Standard polar	33892256
3-methoxybenzene-1,2-diol	COC1=CC=CC(O)=C1O	1251.4	Standard non polar	33892256
3-methoxybenzene-1,2-diol	COC1=CC=CC(O)=C1O	1299.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-methoxybenzene-1,2-diol,1TMS,isomer #1	COC1=CC=CC(O[Si](C)(C)C)=C1O	1388.6	Semi standard non polar	33892256
3-methoxybenzene-1,2-diol,1TMS,isomer #2	COC1=CC=CC(O)=C1O[Si](C)(C)C	1399.5	Semi standard non polar	33892256
3-methoxybenzene-1,2-diol,2TMS,isomer #1	COC1=CC=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	1459.3	Semi standard non polar	33892256
3-methoxybenzene-1,2-diol,1TBDMS,isomer #1	COC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O	1647.8	Semi standard non polar	33892256
3-methoxybenzene-1,2-diol,1TBDMS,isomer #2	COC1=CC=CC(O)=C1O[Si](C)(C)C(C)(C)C	1652.2	Semi standard non polar	33892256
3-methoxybenzene-1,2-diol,2TBDMS,isomer #1	COC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	1960.3	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 - 3-methoxybenzene-1,2-diol GC-MS (2 TMS) - 70eV, Positive	splash10-030u-5490000000-34994c4143398c26f17e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-methoxybenzene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-4900000000-6f5e4598130e5a54ee8d	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-methoxybenzene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-methoxybenzene-1,2-diol 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 - 3-methoxybenzene-1,2-diol 10V, Positive-QTOF	splash10-0006-0900000000-d3bea6e93a92b41a4f7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-methoxybenzene-1,2-diol 20V, Positive-QTOF	splash10-0006-2900000000-2a9e981988d08e64b756	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-methoxybenzene-1,2-diol 40V, Positive-QTOF	splash10-0udi-9200000000-dbdfe5230e3373788221	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-methoxybenzene-1,2-diol 10V, Negative-QTOF	splash10-000i-0900000000-4d23ed5b242331e04f7d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-methoxybenzene-1,2-diol 20V, Negative-QTOF	splash10-000i-2900000000-4e425cadf8b8f947ff32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-methoxybenzene-1,2-diol 40V, Negative-QTOF	splash10-0600-9400000000-8559adb326d3cf53dd61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-methoxybenzene-1,2-diol 10V, Negative-QTOF	splash10-000i-0900000000-eec81e633768bd73c527	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-methoxybenzene-1,2-diol 20V, Negative-QTOF	splash10-00di-3900000000-9e3bd63ad35ca8d01b9a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-methoxybenzene-1,2-diol 40V, Negative-QTOF	splash10-0gb9-9000000000-960f1dec0f4e3dfeb65e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-methoxybenzene-1,2-diol 10V, Positive-QTOF	splash10-052f-2900000000-aa27a19bf9597ae1f94d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-methoxybenzene-1,2-diol 20V, Positive-QTOF	splash10-0f8d-9200000000-cc7a6a3893abf3c2c39d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-methoxybenzene-1,2-diol 40V, Positive-QTOF	splash10-0udi-9000000000-a5da5a433931eda51424	2021-09-25	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 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

FDB084417

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13622

PDB ID

Not Available

ChEBI ID

141700

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, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

3-methoxybenzene-1,2-diol → 2,3-dimethoxyphenol	details
3-methoxybenzene-1,2-diol → 2,6-Dimethoxyphenol	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

3-methoxybenzene-1,2-diol → 3,4,5-trihydroxy-6-(2-hydroxy-6-methoxyphenoxy)oxane-2-carboxylic acid	details
3-methoxybenzene-1,2-diol → 3,4,5-trihydroxy-6-(2-hydroxy-3-methoxyphenoxy)oxane-2-carboxylic acid	details

Showing metabocard for 3-methoxybenzene-1,2-diol (HMDB0125538)

MOL for HMDB0125538 (3-methoxybenzene-1,2-diol)

3D MOL for HMDB0125538 (3-methoxybenzene-1,2-diol)

3D SDF for HMDB0125538 (3-methoxybenzene-1,2-diol)

3D-SDF for HMDB0125538 (3-methoxybenzene-1,2-diol)

PDB for HMDB0125538 (3-methoxybenzene-1,2-diol)

3D PDB for HMDB0125538 (3-methoxybenzene-1,2-diol)

SMILES for HMDB0125538 (3-methoxybenzene-1,2-diol)

INCHI for HMDB0125538 (3-methoxybenzene-1,2-diol)

Structure for HMDB0125538 (3-methoxybenzene-1,2-diol)

3D Structure for HMDB0125538 (3-methoxybenzene-1,2-diol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions