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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2013-04-09 21:16:41 UTC

Update Date

2023-02-21 17:29:39 UTC

HMDB ID

HMDB0059966

Secondary Accession Numbers

HMDB59966

Metabolite Identification

Common Name

3,5-Dimethoxyphenol

Description

3,5-Dimethoxyphenol 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-Dimethoxyphenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,5-Dimethoxyphenol has been detected, but not quantified in, several different foods, such as cumins, white lupines, common salsifies, dates, and herbs and spices. This could make 3,5-dimethoxyphenol a potential biomarker for the consumption of these foods. In such a case, the intoxication can be signalized by the presence of 3,5-dimethoxyphenol in biological material (PMID: 20942244 ). Autopsy findings of fatal intoxication with yew are nonspecific. If yew decoction is consumed, plant residues are not found. A presence of plant residues in the digestive tract can signalize yew intoxication. 3,5-Dimethoxyphenol is a toxin metabolite that can be found in human consuming yew (Taxus baccata) leaves.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
35-Dimethoxyphenol	HMDB
1,3-Dimethoxy-5-hydroxybenzene	HMDB
Phloroglucinol dimethyl ether	HMDB
Phloroglucindimethylether	HMDB
1-Hydroxy-3,5-dimethoxybenzene	HMDB
3,5-Dimethoxyphenol	HMDB
Taxicatigenin	HMDB

Chemical Formula

C₈H₁₀O₃

Average Molecular Weight

154.1632

Monoisotopic Molecular Weight

154.062994186

IUPAC Name

3,5-dimethoxyphenol

Traditional Name

3,5-dimethoxyphenol

CAS Registry Number

500-99-2

SMILES

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

InChI Identifier

InChI=1S/C8H10O3/c1-10-7-3-6(9)4-8(5-7)11-2/h3-5,9H,1-2H3

InChI Key

XQDNFAMOIPNVES-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

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a small molecule (CPD-9499 )

Ontology

Not Available

Urine (PMID: 19812218)

Source

Exogenous

Exogenous (HMDB: HMDB0059966)

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
Water Solubility	11.3 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.35	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.97 m³·mol⁻¹	ChemAxon
Polarizability	15.62 Å³	ChemAxon
Number of Rings	1	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]+	134.087	31661259
DarkChem	[M-H]-	133.133	31661259
DeepCCS	[M+H]+	132.288	30932474
DeepCCS	[M-H]-	128.457	30932474
DeepCCS	[M-2H]-	166.102	30932474
DeepCCS	[M+Na]+	141.642	30932474
AllCCS	[M+H]+	132.5	32859911
AllCCS	[M+H-H2O]+	127.9	32859911
AllCCS	[M+NH4]+	136.7	32859911
AllCCS	[M+Na]+	137.9	32859911
AllCCS	[M-H]-	130.2	32859911
AllCCS	[M+Na-2H]-	131.6	32859911
AllCCS	[M+HCOO]-	133.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dimethoxyphenol	COC1=CC(OC)=CC(O)=C1	2780.0	Standard polar	33892256
3,5-Dimethoxyphenol	COC1=CC(OC)=CC(O)=C1	1393.3	Standard non polar	33892256
3,5-Dimethoxyphenol	COC1=CC(OC)=CC(O)=C1	1464.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dimethoxyphenol,1TMS,isomer #1	COC1=CC(OC)=CC(O[Si](C)(C)C)=C1	1495.2	Semi standard non polar	33892256
3,5-Dimethoxyphenol,1TBDMS,isomer #1	COC1=CC(OC)=CC(O[Si](C)(C)C(C)(C)C)=C1	1734.2	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-Dimethoxyphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-0900000000-6ffc61bab3cb0daf06a4	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dimethoxyphenol GC-MS (1 TMS) - 70eV, Positive	splash10-03k9-7970000000-5fec4139089a0e2011a5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dimethoxyphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,5-Dimethoxyphenol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 40V, Positive-QTOF	splash10-00kb-9000000000-dd3b3735bcca8e69a630	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 20V, Positive-QTOF	splash10-052b-7900000000-eacd2590827ce881ca00	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 10V, Positive-QTOF	splash10-0a4i-0900000000-06b711f0dc96bdfc5673	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 20V, Positive-QTOF	splash10-06r2-6900000000-62834705b287ef331bdb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 10V, Positive-QTOF	splash10-0a4i-0900000000-cbb9850ac89acafe6fef	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 40V, Positive-QTOF	splash10-066s-9000000000-7e6892e595be5d70e9ca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 20V, Negative-QTOF	splash10-052s-4900000000-61963bee977e4ea4b996	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 10V, Negative-QTOF	splash10-000i-0900000000-8ea3f0e77e96fb0968d5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 40V, Negative-QTOF	splash10-0f6t-9000000000-35d5e5055c7b6adcf6d4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 10V, Positive-QTOF	splash10-0a4i-0900000000-ffd8ef068282d660a5a6	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 20V, Positive-QTOF	splash10-0a4i-0900000000-531fc72bb729b51b9353	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 40V, Positive-QTOF	splash10-0abc-9800000000-81c47001436a79575010	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 10V, Negative-QTOF	splash10-0udi-0900000000-f4547a36e0b6f212d68c	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 20V, Negative-QTOF	splash10-0udi-1900000000-90b6b285e82384859fd5	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dimethoxyphenol 40V, Negative-QTOF	splash10-0a4i-9600000000-c7ac2ee075cdab19e48d	2015-05-27	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.421 +/- 0.081 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	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

FDB030390

KNApSAcK ID

Not Available

Chemspider ID

9954

KEGG Compound ID

Not Available

BioCyc ID

CPD-9499

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10383

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

Loke WM, Jenner AM, Proudfoot JM, McKinley AJ, Hodgson JM, Halliwell B, Croft KD: A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. J Nutr. 2009 Dec;139(12):2309-14. doi: 10.3945/jn.109.113613. Epub 2009 Oct 7. [PubMed:19812218 ]
Stribrny J, Dogosi M, Snuparek Z, Toupalik P, Balaz P, Bartos P: [3,5-dimethoxyfenol--marker intoxication with Taxus baccata]. Soud Lek. 2010 Jul;55(3):36-9. [PubMed:20942244 ]

Showing metabocard for 3,5-Dimethoxyphenol (HMDB0059966)

MOL for HMDB0059966 (3,5-Dimethoxyphenol)

3D MOL for HMDB0059966 (3,5-Dimethoxyphenol)

3D SDF for HMDB0059966 (3,5-Dimethoxyphenol)

3D-SDF for HMDB0059966 (3,5-Dimethoxyphenol)

PDB for HMDB0059966 (3,5-Dimethoxyphenol)

3D PDB for HMDB0059966 (3,5-Dimethoxyphenol)

SMILES for HMDB0059966 (3,5-Dimethoxyphenol)

INCHI for HMDB0059966 (3,5-Dimethoxyphenol)

Structure for HMDB0059966 (3,5-Dimethoxyphenol)

3D Structure for HMDB0059966 (3,5-Dimethoxyphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra