ContaminantDB: Vanylglycol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:11:41 UTC

Update Date

2016-11-09 01:17:21 UTC

Accession Number

CHEM021755

Identification

Common Name

Vanylglycol

Class

Small Molecule

Description

Vanylglycol (MHPG) is a O-methylated metabolite of normetanephrine. MHPG is formed by catechol-O-methyltransferase (COMT) from norepinephrine. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. Catecholamines are substantially increased during stress, exercise or smoking and could result in clinically important platelet activation if their action was not rapidly regulated. MHPG is found normally in urine, in plasma and cerebrospinal fluid. Alcohol consumption increases the level of HMPG in urine and CSF. Alcohol dehydrogenase has been shown to act on norepinephrine and produce HMPG. (PMID: 11958479, 9706478, 7735466, 2455302) [HMDB]. Vanylglycol is found in many foods, some of which are chervil, pummelo, peanut, and onion-family vegetables.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(4-Hydroxy-3-methoxyphenyl)-1,2-ethanediol	HMDB
3-Methoxy-4-hydroxyphenethylene glycol	HMDB
3-Methoxy-4-hydroxyphenyl glycol	HMDB
4-Hydroxy-3-methoxy-b-phenylglycol	HMDB
4-Hydroxy-3-methoxy-beta-phenylglycol	HMDB
4-Hydroxy-3-methoxyphenyl glycol	HMDB
HMPG	HMDB
Hydroxymethoxyphenylglycol	HMDB, MeSH
Methoxyhydroxyphenylglycol	HMDB, MeSH
MHPG	HMDB, MeSH
MOPEG	HMDB, MeSH
4 Hydroxy 3 methoxyphenylethyleneglycol	MeSH, HMDB
4 Hydroxy 3 methoxyphenylglycol	MeSH, HMDB
4-Hydroxy-3-methoxyphenylethyleneglycol	MeSH, HMDB
Methoxyhydroxyphenylglycol, (-)-isomer	MeSH, HMDB
4 Hydroxy 3 methoxyphenylethylene glycol	MeSH, HMDB
4-Hydroxy-3-methoxyphenylglycol	MeSH, HMDB
Methoxyhydroxyphenylglycol, (+)-isomer	MeSH, HMDB
4-Hydroxy-3-methoxyphenylethylene glycol	MeSH, HMDB
Methoxyhydroxyphenylglycol, (+-)-isomer	MeSH, HMDB

Chemical Formula

C₉H₁₂O₄

Average Molecular Mass

184.189 g/mol

Monoisotopic Mass

184.074 g/mol

CAS Registry Number

534-82-7

IUPAC Name

1-(4-hydroxy-3-methoxyphenyl)ethane-1,2-diol

Traditional Name

methoxyhydroxyphenylglycol

SMILES

COC1=CC(=CC=C1O)C(O)CO

InChI Identifier

InChI=1S/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3

InChI Key

FBWPWWWZWKPJFL-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
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Secondary alcohol
1,2-diol
Ether
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:1576 )
methoxybenzene (CHEBI:1576 )
a guaiacol (CPD-11497 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	8.99 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	0.11	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.28 m³·mol⁻¹	ChemAxon
Polarizability	18.64 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-2900000000-85ebe9a57a84ddca41b6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0079-7149000000-54b71f18882477571deb	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0uxr-0900000000-fb2c82b5598c8c9bab3a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-0900000000-a449b185542d66dc0be8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-006x-9600000000-316d1194b9b0ed76d178	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-f104dd3883189a74b622	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-0900000000-040295df7423a417edab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f72-3900000000-87310e73492350a05b5c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-01cbe4fce361c48afabf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05ur-1900000000-b4ac6a118c11eb31a6ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-4a1c057f8cdd445e7125	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004r-0900000000-df828b6c78ec969e404f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-4900000000-97f0c28e2ac7713a8fc5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9100000000-ed2fd3623e179bd8e27f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-0900000000-9b55b059e2dc27b7380f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-2900000000-44ed0b094433b8f04721	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053u-6900000000-4de993e85915570061f3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0259702

FooDB ID

FDB022651

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

10348

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C05594

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Vanylglycol (CHEM021755)

Structure for CHEM021755: Vanylglycol