Bovine Metabolome Database: Showing metabocard for Vanylglycol (BMDB0001490)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:46:41 UTC

Update Date

2020-05-21 16:27:04 UTC

BMDB ID

BMDB0001490

Secondary Accession Numbers

BMDB01490

Metabolite Identification

Common Name

Vanylglycol

Description

Vanylglycol, also known as MHPG or vanylglycol, 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. Vanylglycol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Vanylglycol and pyrocatechol can be biosynthesized from 3,4-dihydroxyphenylglycol and guaiacol through its interaction with the enzyme catechol O-methyltransferase. In cattle, vanylglycol is involved in the metabolic pathway called the tyrosine metabolism pathway.

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 Weight

184.1892

Monoisotopic Molecular Weight

184.073558872

IUPAC Name

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

Traditional Name

methoxyhydroxyphenylglycol

CAS Registry Number

534-82-7

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 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

Experimental 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

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-2900000000-85ebe9a57a84ddca41b6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0079-7149000000-54b71f18882477571deb	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0uxr-0900000000-fb2c82b5598c8c9bab3a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00di-0900000000-a449b185542d66dc0be8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-006x-9600000000-316d1194b9b0ed76d178	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-f104dd3883189a74b622	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-0900000000-040295df7423a417edab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f72-3900000000-87310e73492350a05b5c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-01cbe4fce361c48afabf	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05ur-1900000000-b4ac6a118c11eb31a6ff	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-4a1c057f8cdd445e7125	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004r-0900000000-df828b6c78ec969e404f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-4900000000-97f0c28e2ac7713a8fc5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-9100000000-ed2fd3623e179bd8e27f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-0900000000-9b55b059e2dc27b7380f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-2900000000-44ed0b094433b8f04721	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053u-6900000000-4de993e85915570061f3	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Brain
Platelet

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tyrosine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0259702

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022651

KNApSAcK ID

Not Available

Chemspider ID

10348

KEGG Compound ID

C05594

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Kessler J A; Gordon E K; Reid J L; Kopin I J Homovanillic acid and 3-methoxy-4-hydroxyphenylethyleneglycol production by the monkey spinal cord. Journal of neurochemistry (1976), 26(6), 1057-61.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

General function:: Involved in catechol O-methyltransferase activity
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 (By similarity).
Gene Name:: COMT
Uniprot ID:: A7MBI7
Molecular weight:: 30485.0

Reactions

3,4-Dihydroxyphenylglycol + Guaiacol → Vanylglycol + Pyrocatechol	details

Showing metabocard for Vanylglycol (BMDB0001490)

Structure for BMDB0001490 (Vanylglycol)

Enzymes

Reactions