Livestock Metabolome Database: Showing metabocard for Vanillylmandelic acid (LMDB00129)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:43:00 UTC

Update Date

2016-07-20 21:03:27 UTC

Lmdb

LMDB00129

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vanillylmandelic acid

Description

Vanillylmandelic acid, also known as vanillylmandelate or VMA, 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 is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanillylmandelic acid exists in all living organisms, ranging from bacteria to humans. Within humans, vanillylmandelic acid participates in a number of enzymatic reactions. In particular, vanillylmandelic acid can be biosynthesized from 3-methoxy-4-hydroxyphenylglycolaldehyde through its interaction with the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, vanillylmandelic acid and pyrocatechol can be biosynthesized from 3,4-dihydroxymandelic acid and guaiacol through the action of the enzyme catechol O-methyltransferase. Specifically the reaction entails the condensation of guaiacol and glyoxylic acid in an ice cold, aqueous solution with sodium hydroxide. In humans, vanillylmandelic acid is involved in the metabolic disorder called tyrosinemia type I. Vanillylmandelic acid is a sweet and vanilla tasting compound. Outside of the human body,. Vanillylmandelic acid, with regard to humans, has been found to be associated with several diseases such as brunner syndrome, colorectal cancer, and eosinophilic esophagitis; vanillylmandelic acid has also been linked to several inborn metabolic disorders including aromatic l-amino acid decarboxylase deficiency and phenylketonuria. In timed urine tests the quantity excreted (usually per 24 hours) is assessed along with creatinine clearance, and the quantity of cortisols, catecholamines, and metanephrines excreted is also measured. Urinary VMA is elevated in patients with tumors that secrete catecholamines. These tests may also be used to diagnose neuroblastomas, and to monitor treatment of these conditions. These hormones are released into the blood during times of physical or emotional stress, which are factors that may skew the results of the test. Vanillylmandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings and is an end-stage metabolite of the catecholamines (dopamine, epinephrine, and norepinephrine). Norepinephrine is one of the hormones produced by the adrenal glands, which are found on top of the kidneys. These urinalysis tests are used to diagnose an adrenal gland tumor called pheochromocytoma, a tumor of catecholamine-secreting chromaffin cells. VMA synthesis is the first step of a two-step process practiced by Rhodia since the 1970s to synthesize artificial vanilla. Norepinephrine is metabolised into normetanephrine and VMA. It is produced via intermediary metabolites.

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

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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	0.94	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

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-3900000000-97b85fd5a9736a5d5eb0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-009t-7396100000-b5450c24921a68f5f6b3	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)	splash10-000b-0900000000-1e2dedd8e81249787b29	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000i-0900000000-3d2cd918dc6b76dfba3f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000i-2900000000-b543807e43e5091abb53	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1900000000-1c88ce4d32680e3379de	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-30e1c8cb4fa5443c687e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-c4c762f850d22fee6281	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-0900000000-1308d37a2313f5479365	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fmj-0900000000-bcdff30bcec2389ffef6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-3900000000-cd2db271b5a0926adfeb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dj-9700000000-2c212037a037fcd229d0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kg9-1900000000-81b2ab77bf3382c9f5de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-4900000000-e3b77a4d29235649ecce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f8a-0900000000-04d80bfab4984d07e479	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-23d4830296b7ea07f0d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fki-5900000000-9b9364530caece4b6c12	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f7t-0900000000-ac32d971a0581e8b6cb6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-bce2f2854f319781df10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0umi-9700000000-311af8dc825e2dd02614	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum