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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-17 19:04:05 UTC

Update Date

2023-02-21 17:32:22 UTC

HMDB ID

HMDB0132905

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,5-Dihydroxyanisole

Description

3,5-Dihydroxyanisole, also known as 5-methoxyresorcinol or flamenol, 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. 3,5-Dihydroxyanisole is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,5-dihydroxyanisole has been detected, but not quantified in, several different foods, such as annual wild rice, prairie turnips, thistles, grapefruit/pummelo hybrids, and pecan nuts. This could make 3,5-dihydroxyanisole a potential biomarker for the consumption of these foods. BioTransformer predicts that 3,5-dihydroxyanisole is a product of helichrysetin 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
3,5-Dihydroxyanisole	ChEBI
5-Methoxyresorcinol	ChEBI
Flamenolum	ChEBI
Phloroglucinol monomethyl ether	ChEBI
1,3-Dihydroxy-5-methoxybenzene	HMDB
1-Methoxy-3,5-benzenediol	HMDB
3-Hydroxy-5-methoxyphenol	HMDB
5-Methoxy-1,3-benzenediol	HMDB
5-Methoxybenzene-1,3-diol	HMDB
Flamenol	HMDB
Monomethylphloroglucinol	HMDB
O-Methylphloroglucinol	HMDB

Chemical Formula

C₇H₈O₃

Average Molecular Weight

140.1366

Monoisotopic Molecular Weight

140.047344122

IUPAC Name

5-methoxybenzene-1,3-diol

Traditional Name

3,5-dihydroxyanisole

CAS Registry Number

2174-64-3

SMILES

COC1=CC(O)=CC(O)=C1

InChI Identifier

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

InChI Key

HDVRLUFGYQYLFJ-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

a small molecule (CPD-9494 )

Ontology

Not Available

Not Available

Not Available

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	0.63	ALOGPS
logP	1.21	ChemAxon
logS	-0.52	ALOGPS
pKa (Strongest Acidic)	9.23	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	13.68 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]+	130.185	31661259
DarkChem	[M-H]-	128.035	31661259
DeepCCS	[M+H]+	127.111	30932474
DeepCCS	[M-H]-	123.279	30932474
DeepCCS	[M-2H]-	160.558	30932474
DeepCCS	[M+Na]+	136.098	30932474
AllCCS	[M+H]+	129.2	32859911
AllCCS	[M+H-H2O]+	124.5	32859911
AllCCS	[M+NH4]+	133.6	32859911
AllCCS	[M+Na]+	134.8	32859911
AllCCS	[M-H]-	124.4	32859911
AllCCS	[M+Na-2H]-	126.2	32859911
AllCCS	[M+HCOO]-	128.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dihydroxyanisole	COC1=CC(O)=CC(O)=C1	2956.7	Standard polar	33892256
3,5-Dihydroxyanisole	COC1=CC(O)=CC(O)=C1	1518.8	Standard non polar	33892256
3,5-Dihydroxyanisole	COC1=CC(O)=CC(O)=C1	1536.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dihydroxyanisole,1TMS,isomer #1	COC1=CC(O)=CC(O[Si](C)(C)C)=C1	1557.3	Semi standard non polar	33892256
3,5-Dihydroxyanisole,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1	1560.3	Semi standard non polar	33892256
3,5-Dihydroxyanisole,1TBDMS,isomer #1	COC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1	1794.8	Semi standard non polar	33892256
3,5-Dihydroxyanisole,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1	2018.5	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 - 3,5-Dihydroxyanisole GC-MS (2 TMS) - 70eV, Positive	splash10-02mi-3290000000-e6badc3df058af4c9447	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dihydroxyanisole GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0900000000-8b17193ee9c420df491c	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dihydroxyanisole 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 - 3,5-Dihydroxyanisole 10V, Positive-QTOF	splash10-0006-0900000000-c08fc4f91c6bb54d8c0b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxyanisole 20V, Positive-QTOF	splash10-0006-0900000000-81888d3f003071f2075d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxyanisole 40V, Positive-QTOF	splash10-01vo-9800000000-caaf826ab9546baa2168	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxyanisole 10V, Negative-QTOF	splash10-000i-0900000000-d58cc2291bedc48b835c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxyanisole 20V, Negative-QTOF	splash10-000i-1900000000-59f5a7dfc17a60818ad6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxyanisole 40V, Negative-QTOF	splash10-0a4i-9400000000-efff12b14164304096a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxyanisole 10V, Negative-QTOF	splash10-000i-0900000000-eec81e633768bd73c527	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxyanisole 20V, Negative-QTOF	splash10-000i-2900000000-7a9a5658af0127f1e044	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxyanisole 40V, Negative-QTOF	splash10-0006-9000000000-d4878cfbe89e6812eec4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxyanisole 10V, Positive-QTOF	splash10-0006-0900000000-876efd290e4df926cd0c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxyanisole 20V, Positive-QTOF	splash10-0007-7900000000-679a073b31df5a3c4f24	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxyanisole 40V, Positive-QTOF	splash10-000f-9000000000-ddd3436f828ec8686f82	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

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

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

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

FDB030389

KNApSAcK ID

Not Available

Chemspider ID

64709

KEGG Compound ID

Not Available

BioCyc ID

CPD-9494

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71648

PDB ID

Not Available

ChEBI ID

136806

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 3,5-Dihydroxyanisole (HMDB0132905)

MOL for HMDB0132905 (3,5-Dihydroxyanisole)

3D MOL for HMDB0132905 (3,5-Dihydroxyanisole)

3D SDF for HMDB0132905 (3,5-Dihydroxyanisole)

3D-SDF for HMDB0132905 (3,5-Dihydroxyanisole)

PDB for HMDB0132905 (3,5-Dihydroxyanisole)

3D PDB for HMDB0132905 (3,5-Dihydroxyanisole)

SMILES for HMDB0132905 (3,5-Dihydroxyanisole)

INCHI for HMDB0132905 (3,5-Dihydroxyanisole)

Structure for HMDB0132905 (3,5-Dihydroxyanisole)

3D Structure for HMDB0132905 (3,5-Dihydroxyanisole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra