Bovine Metabolome Database: Showing metabocard for Vanillylmandelic acid (BMDB0000291)

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

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:55 UTC

Update Date

2020-05-21 16:28:47 UTC

BMDB ID

BMDB0000291

Secondary Accession Numbers

BMDB00291

Metabolite Identification

Common Name

Vanillylmandelic acid

Description

Vanillylmandelic acid, also known as vanillylmandelic acid or vanillylmandelic acid CPD, 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. Vanillylmandelic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Vanillylmandelic acid exists in all living organisms, ranging from bacteria to humans. Vanillylmandelic acid participates in a number of enzymatic reactions, within cattle. In particular, Vanillylmandelic acid can be biosynthesized from 3-methoxy-4-hydroxyphenylglycolaldehyde through the action of the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, Vanillylmandelic acid and pyrocatechol can be biosynthesized from 3,4-dihydroxymandelic acid and guaiacol; which is catalyzed by the enzyme catechol O-methyltransferase. In cattle, vanillylmandelic acid is involved in the metabolic pathway called the tyrosine metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Vanillylmandelate	Generator
(4-Hydroxy-3-methoxyphenyl)glycolate	HMDB
(4-Hydroxy-3-methoxyphenyl)glycolic acid	HMDB
3-Methoxy-4-hydroxy-mandelic acid	HMDB
3-Methoxy-4-hydroxymandelate	HMDB
3-Methoxy-4-hydroxymandelic acid	HMDB
3-Methoxy-4-hydroxyphenylhydroxyacetate	HMDB
3-Methoxy-4-hydroxyphenylhydroxyacetic acid	HMDB
4'-Hydroxy-3'-methoxymandelate	HMDB
4'-Hydroxy-3'-methoxymandelic acid	HMDB
4-Hydroxy 3-methoxymandelic acid	HMDB
4-Hydroxy-3-methoxy-DL-mandelate	HMDB
4-Hydroxy-3-methoxy-DL-mandelic acid	HMDB
4-Hydroxy-3-methoxy-mandelate	HMDB
4-Hydroxy-3-methoxy-mandelic acid	HMDB
4-Hydroxy-3-methoxymandelate	HMDB
4-Hydroxy-3-methoxymandelic acid	HMDB
DL-3-Methoxy-4-hydroxymandelate	HMDB
DL-3-Methoxy-4-hydroxymandelic acid	HMDB
DL-4-Hydroxy-3-methoxymandelate	HMDB
DL-4-Hydroxy-3-methoxymandelic acid	HMDB
DL-Vanillomandelate	HMDB
DL-Vanillomandelic acid	HMDB
DL-Vanillylmandelate	HMDB
DL-Vanillylmandelic acid	HMDB
HMMA	HMDB
Hydroxymethoxymandelic acid	HMDB
Lopac-H-0131	HMDB
Vainillylmandelic acid	HMDB
Vanillinmandelate	HMDB
Vanillinmandelic acid	HMDB
Vanillomandelate	HMDB
Vanillomandelic acid	HMDB
Vanillyl-mandelic acid	HMDB
Vanillylmandellic acid	HMDB
Vanillymandelic acid	HMDB
Vanilmandelate	HMDB
Vanilmandelic acid	HMDB
Vanilylmandelic acid	HMDB
Vanyl-mandelic acid	HMDB
Vanylmandelic acid	HMDB
VMA	HMDB
2-Phenyllactic acid	HMDB
VMA CPD	HMDB
Atrolactic acid	HMDB
Atrolactic acid monosodium salt, (S)-isomer	HMDB
Atrolactic acid, (+-)-isomer	HMDB
Hydroxymethylmandelic acid	HMDB
(+)-4-Hydroxy-3-methoxymandelic acid	HMDB
(+)-Vanilmandelic acid	HMDB
(2S)-2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid	HMDB
(S)-4-Hydroxy-3-methoxymandelic acid	HMDB
(alphaS)-alpha,4-Dihydroxy-3-methoxybenzeneacetic acid	HMDB
(αS)-α,4-Dihydroxy-3-methoxybenzeneacetic acid	HMDB
2-(4'-Hydroxy-3'-methoxyphenyl)-2-hydroxyethanoic acid	HMDB
2-(4’-Hydroxy-3’-methoxyphenyl)-2-hydroxyethanoic acid	HMDB
2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid	HMDB
4’-Hydroxy-3’-methoxymandelic acid	HMDB
L-(+)-3-Methoxy-4-hydroxymandelic acid	HMDB
Vanillylmandelic acid	HMDB
alpha,4-Dihydroxy-3-methoxybenzeneacetic acid	HMDB
α,4-Dihydroxy-3-methoxybenzeneacetic acid	HMDB

Chemical Formula

C₉H₁₀O₅

Average Molecular Weight

198.1727

Monoisotopic Molecular Weight

198.05282343

IUPAC Name

(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid

Traditional Name

(S)-hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid

CAS Registry Number

55-10-7

SMILES

COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O

InChI Identifier

InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m0/s1

InChI Key

CGQCWMIAEPEHNQ-QMMMGPOBSA-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
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Alpha-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	132 - 134 °C	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	0.94	ALOGPS
logP	0.43	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.11	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.15 m³·mol⁻¹	ChemAxon
Polarizability	18.45 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

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adrenal Gland
Epidermis
Thyroid Gland

Pathways

Name	SMPDB/Pathwhiz	KEGG
Tyrosine Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Thyroid Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000291

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021931

KNApSAcK ID

Not Available

Chemspider ID

643307

KEGG Compound ID

C05584

BioCyc ID

Not Available

BiGG ID

46071

Wikipedia Link

Vanillylmandelic acid

METLIN ID

697

PubChem Compound

736172

PDB ID

Not Available

ChEBI ID

1127735

References

Synthesis Reference

Recondo, E. F.; Rinderknecht, H. Preparation of epinephrine and norepinephrine metabolites, 3-methoxy-4-hydroxymandelic acid and 3,4-dihydroxymandelic acid. Journal of Organic Chemistry (1960), 25 2248-50.

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-Dihydroxymandelic acid + Guaiacol → Vanillylmandelic acid + Pyrocatechol	details

Enzyme Details

2. Aldehyde dehydrogenase family 3 member B1

General function:: Energy production and conversion
Specific function:: Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. Can use both NADP(+) and NAD(+) as electron acceptor. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:: ALDH3B1
Uniprot ID:: Q1JPA0
Molecular weight:: 51800.0

Reactions

3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH	details

Showing metabocard for Vanillylmandelic acid (BMDB0000291)

Structure for BMDB0000291 (Vanillylmandelic acid)

Enzymes

Reactions

Reactions