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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:41 UTC

HMDB ID

HMDB0000291

Secondary Accession Numbers

HMDB00291
HMDB0133489

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 a sweet and vanilla tasting compound. 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). Vanillylmandelic acid exists in all living organisms, ranging from bacteria to plants 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. 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. Urinary VMA is elevated in patients with tumors that secrete catecholamines. Urinary VMA tests may also be used to diagnose neuroblastomas, and to monitor treatment of these conditions. VMA urinalysis tests can be used to diagnose an adrenal gland tumor called pheochromocytoma, a tumor of catecholamine-secreting chromaffin cells. Vanillylmandelic acid (VMA) is produced in the liver and is a major product of norepinephrine and epinephrine metabolism excreted in the urine.

Structure

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

  Mrv1652309272019172D          

 14 14  0  0  0  0            999 V2000
10001.055910000.4128    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.7701 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.055910001.2385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.484410000.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.7701 9999.1752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.192710000.4128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4755 9999.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1927 9998.7614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.338610000.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.624110000.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9096 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9095 9999.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6240 9998.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3386 9999.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  6  0  0  0
  2  4  1  0  0  0  0
  2  5  2  0  0  0  0
  6  7  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14  9  1  0  0  0  0
  1  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000291

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C9H10O5

> <MOLECULAR_WEIGHT>
198.1727

> <EXACT_MASS>
198.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.45199272440707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
0.43459905733333315

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.913823964089037

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.113631257291667

> <JCHEM_PKA_STRONGEST_BASIC>
-4.128024057113833

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
47.14790000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.6388667.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.9718666.666   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8668.6388668.979   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8671.3048667.437   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8669.9718665.127   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8663.2938667.437   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8661.9548666.665   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8663.2938664.355   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8667.2998666.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.9658667.436   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6318666.666   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.6318665.126   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.9658664.356   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.2998665.127   0.000  0.00  0.00           C+0
CONECT    1    2    3    9                                                  
CONECT    2    1    4    5                                                  
CONECT    3    1                                                            
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    7   11                                                       
CONECT    7    6                                                            
CONECT    8   12                                                            
CONECT    9   10   14    1                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12    6                                                  
CONECT   12   11   13    8                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

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

13244-77-4

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

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Aromatic L-amino acid decarboxylase deficiency (HMDB: HMDB0000291)

Organoleptic effect

Taste

Sweet

Odor

Vanilla

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)
Saliva (PMID: 24421258)

Epidermis (HMDB: HMDB0000291)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 25037050)

Cellular substructure

Cytoplasm (HMDB: HMDB0000291)

Source

Endogenous

Endogenous (HMDB: HMDB0000291)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (PathBank: SMP0087328)
Tyrosine Metabolism (HMDB: HMDB0000291)

Disease pathway

Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)

Drug action pathway

Disulfiram Action Pathway (HMDB: HMDB0000291)
Disulfiram Action Pathway (PathBank: SMP0000429)

Role

Industrial application

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00000136)
Aromatic L-amino acid decarboxylase deficiency (MarkerDB: MDB00000136)
Brunner Syndrome (MarkerDB: MDB00000136)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	140.904	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000288

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.16 g/L	ALOGPS
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	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	146.289	31661259
DarkChem	[M-H]-	146.476	31661259
AllCCS	[M+H]+	143.798	32859911
AllCCS	[M-H]-	139.896	32859911
DeepCCS	[M+H]+	144.715	30932474
DeepCCS	[M-H]-	142.34	30932474
DeepCCS	[M-2H]-	175.899	30932474
DeepCCS	[M+Na]+	150.791	30932474
AllCCS	[M+H]+	143.8	32859911
AllCCS	[M+H-H2O]+	139.7	32859911
AllCCS	[M+NH4]+	147.6	32859911
AllCCS	[M+Na]+	148.7	32859911
AllCCS	[M-H]-	139.9	32859911
AllCCS	[M+Na-2H]-	140.6	32859911
AllCCS	[M+HCOO]-	141.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vanillylmandelic acid	COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O	3318.2	Standard polar	33892256
Vanillylmandelic acid	COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O	1822.7	Standard non polar	33892256
Vanillylmandelic acid	COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O	1769.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vanillylmandelic acid,1TMS,isomer #1	COC1=CC([C@H](O)C(=O)O)=CC=C1O[Si](C)(C)C	1885.0	Semi standard non polar	33892256
Vanillylmandelic acid,1TMS,isomer #2	COC1=CC([C@H](O[Si](C)(C)C)C(=O)O)=CC=C1O	1852.5	Semi standard non polar	33892256
Vanillylmandelic acid,1TMS,isomer #3	COC1=CC([C@H](O)C(=O)O[Si](C)(C)C)=CC=C1O	1814.7	Semi standard non polar	33892256
Vanillylmandelic acid,2TMS,isomer #1	COC1=CC([C@H](O[Si](C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C	1884.8	Semi standard non polar	33892256
Vanillylmandelic acid,2TMS,isomer #2	COC1=CC([C@H](O)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1880.9	Semi standard non polar	33892256
Vanillylmandelic acid,2TMS,isomer #3	COC1=CC([C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O	1897.2	Semi standard non polar	33892256
Vanillylmandelic acid,3TMS,isomer #1	COC1=CC([C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1912.8	Semi standard non polar	33892256
Vanillylmandelic acid,1TBDMS,isomer #1	COC1=CC([C@H](O)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2170.0	Semi standard non polar	33892256
Vanillylmandelic acid,1TBDMS,isomer #2	COC1=CC([C@H](O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O	2138.0	Semi standard non polar	33892256
Vanillylmandelic acid,1TBDMS,isomer #3	COC1=CC([C@H](O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2073.1	Semi standard non polar	33892256
Vanillylmandelic acid,2TBDMS,isomer #1	COC1=CC([C@H](O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	2416.3	Semi standard non polar	33892256
Vanillylmandelic acid,2TBDMS,isomer #2	COC1=CC([C@H](O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2359.0	Semi standard non polar	33892256
Vanillylmandelic acid,2TBDMS,isomer #3	COC1=CC([C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	2371.1	Semi standard non polar	33892256
Vanillylmandelic acid,3TBDMS,isomer #1	COC1=CC([C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2582.2	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 - Vanillylmandelic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-3900000000-97b85fd5a9736a5d5eb0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (3 TMS) - 70eV, Positive	splash10-009t-7396100000-b5450c24921a68f5f6b3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanillylmandelic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vanillylmandelic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-000b-0900000000-1e2dedd8e81249787b29	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vanillylmandelic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-000i-0900000000-3d2cd918dc6b76dfba3f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vanillylmandelic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-000i-2900000000-b543807e43e5091abb53	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vanillylmandelic acid 40V, Negative-QTOF	splash10-000i-1900000000-1c88ce4d32680e3379de	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vanillylmandelic acid 10V, Negative-QTOF	splash10-000i-0900000000-30e1c8cb4fa5443c687e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vanillylmandelic acid 20V, Negative-QTOF	splash10-000i-0900000000-c4c762f850d22fee6281	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 10V, Negative-QTOF	splash10-0f6t-0900000000-1308d37a2313f5479365	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 20V, Negative-QTOF	splash10-0fmj-0900000000-bcdff30bcec2389ffef6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 40V, Negative-QTOF	splash10-0ab9-3900000000-cd2db271b5a0926adfeb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 10V, Negative-QTOF	splash10-00dj-9700000000-2c212037a037fcd229d0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 20V, Negative-QTOF	splash10-0kg9-1900000000-81b2ab77bf3382c9f5de	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 40V, Negative-QTOF	splash10-0002-4900000000-e3b77a4d29235649ecce	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 10V, Positive-QTOF	splash10-0f8a-0900000000-04d80bfab4984d07e479	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 20V, Positive-QTOF	splash10-0udi-0900000000-23d4830296b7ea07f0d5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 40V, Positive-QTOF	splash10-0fki-5900000000-9b9364530caece4b6c12	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 10V, Positive-QTOF	splash10-0f7t-0900000000-ac32d971a0581e8b6cb6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 20V, Positive-QTOF	splash10-000i-0900000000-bce2f2854f319781df10	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanillylmandelic acid 40V, Positive-QTOF	splash10-0umi-9700000000-311af8dc825e2dd02614	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Adrenal Gland
Epidermis
Thyroid Gland

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Alkaptonuria		Not Available
Hawkinsinuria		Not Available
Tyrosinemia Type I		Not Available
Tyrosinemia, transient, of the newborn		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.035 +/- 0.008 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Urine	Detected and Quantified	4.906 +/- 1.769 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	5.0776 +/- 1.712 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	5.135 +/- 1.826 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	9439441	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	6.2 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	21670092	details
Urine	Detected and Quantified	1.585 +/- 1.095 umol/mmol creatinine	Adult (>18 years old)	Both	Not Available	9439441	details
Urine	Detected and Quantified	3.67 +/- 2.12 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected and Quantified	7.758 +/- 2.944 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	13.24 +/- 5.3 umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	24296288	details
Urine	Detected and Quantified	5.38 +/- 1.83 umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	24296288	details
Urine	Detected and Quantified	4.18 +/- 1.55 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	24556394	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	6.19 +/- 2.014 umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	24769278	details
Urine	Detected and Quantified	6.22 +/- 2.32 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	24769278	details
Urine	Detected and Quantified	10.0 (0.3-20.0) umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	16288991	details
Urine	Detected and Quantified	3.22-9.08 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	24769278	details
Urine	Detected and Quantified	5.68 +/- 2.19 umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	24769278	details
Urine	Detected and Quantified	5.93 +/- 3.016 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	1.6-2.2 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	2.3 (1.0-3.4) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	1.2 +/- 0.5 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15992788	details
Urine	Detected and Quantified	0.300-19.700 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	9686366	details
Urine	Detected and Quantified	1.1-1.7 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	0.5-7.6 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	8503438	details
Urine	Detected and Quantified	12.5 (3.7-21.8) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	12.4 (11.6-25.9) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	6.5 (1.3-11.5) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	6.5 (2.9-13.0) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	5.2 (2.5-16.1) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	<=3.289 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	978-0-911910-19-3	details
Urine	Detected and Quantified	1.6 (0.6-2.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	9.128 +/- 4.450 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	7.586 +/- 3.852 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	7.332 +/- 3.711 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	0.15 (0.00-0.30) umol/mmol creatinine	Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	16288991	details
Urine	Detected and Quantified	6.869 +/- 2.756 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details
Urine	Detected and Quantified	0.2-0.4 umol/mmol creatinine	Adult (>18 years old)	Male	Brunner Syndrome	8503438	details
Urine	Detected and Quantified	0.5 umol/mmol creatinine	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details
Urine	Detected and Quantified	0.9 umol/mmol creatinine	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	9686366	details
Urine	Detected and Quantified	15.404 +/- 14.833 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	4.564 +/- 1.369 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Aromatic L-amino acid decarboxylase deficiency
Abdenur JE, Abeling N, Specola N, Jorge L, Schenone AB, van Cruchten AC, Chamoles NA: Aromatic l-aminoacid decarboxylase deficiency: unusual neonatal presentation and additional findings in organic acid analysis. Mol Genet Metab. 2006 Jan;87(1):48-53. Epub 2005 Nov 9. [PubMed:16288991 ] Abeling NG, van Gennip AH, Barth PG, van Cruchten A, Westra M, Wijburg FA: Aromatic L-amino acid decarboxylase deficiency: a new case with a mild clinical presentation and unexpected laboratory findings. J Inherit Metab Dis. 1998 Jun;21(3):240-2. [PubMed:9686366 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Phenylketonuria
Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
Brunner Syndrome
Brunner HG, Nelen MR, van Zandvoort P, Abeling NG, van Gennip AH, Wolters EC, Kuiper MA, Ropers HH, van Oost BA: X-linked borderline mental retardation with prominent behavioral disturbance: phenotype, genetic localization, and evidence for disturbed monoamine metabolism. Am J Hum Genet. 1993 Jun;52(6):1032-9. [PubMed:8503438 ]

Associated OMIM IDs

114500 (Colorectal cancer)
608643 (Aromatic L-amino acid decarboxylase deficiency)
610247 (Eosinophilic esophagitis)
261600 (Phenylketonuria)
300615 (Brunner Syndrome)

External Links

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

Food Biomarker Ontology

Not Available

VMH ID

3MOX4HOXM

MarkerDB ID

MDB00000136

Good Scents ID

Not Available

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

Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]
Silbergeld EK, Chisolm JJ Jr: Lead poisoning: altered urinary catecholamine metabolites as indicators of intoxication in mice and children. Science. 1976 Apr 9;192(4235):153-5. [PubMed:1257763 ]
Frank K, Raue F, Gottswinter J, Heinrich U, Meybier H, Ziegler R: Importance of early diagnosis and follow-up in multiple endocrine neoplasia (MEN II B). Eur J Pediatr. 1984 Dec;143(2):112-6. [PubMed:6394335 ]
Takahashi S, Godse DD, Warsh JJ, Stancer HC: A gas chromatographic-mass spectrometric (GC-MS) assay for 3-methoxy-4-hydroxyphenethyleneglycol and vanilmandelic acid in human serum. Clin Chim Acta. 1977 Dec 1;81(2):182-92. [PubMed:589798 ]
Suga K, Shimizu K, Nishigauchi K, Kume N, Kawamura T, Matsunaga N: [A case of bilateral adrenal neuroblastomas detected by bone scintigraphy]. Kaku Igaku. 1996 Dec;33(12):1337-42. [PubMed:9023440 ]
Hartleb J, Eue S, Kemper A: Simultaneous analysis of homovanillic acid, 5-hydroxyindoleacetic acid, 3-methoxy-4-hydroxyphenylethylene glycol and vanilmandelic acid in plasma from alcoholics by high-performance liquid chromatography with electrochemical detection. Critical comparison of solid-phase and liquid-liquid extraction methods. J Chromatogr. 1993 Dec 22;622(2):161-71. [PubMed:7512090 ]
Dias PL, Amarasiri AA: 4-hydroxy-3-methoxymandelic acid (HMMA) excretion in retinoblastoma. Br J Ophthalmol. 1978 Aug;62(8):525-7. [PubMed:687548 ]
Saran RK, Sahuja RC, Gupta NN, Hasan M, Bhargava KP, Shanker K, Kishor K: 3-Methoxy-4-hydroxyphenylglycol in cerebrospinal fluid and vanillylmandelic acid in urine of humans with hypertension. Science. 1978 Apr 21;200(4339):317-8. [PubMed:635588 ]
Strittmatter M, Grauer M, Isenberg E, Hamann G, Fischer C, Hoffmann KH, Blaes F, Schimrigk K: Cerebrospinal fluid neuropeptides and monoaminergic transmitters in patients with trigeminal neuralgia. Headache. 1997 Apr;37(4):211-6. [PubMed:9150615 ]
Zambotti F, Blau K, King GS, Campbell S, Sandler M: Monoamine metabolites and related compounds in human amniotic fluid: assay by gas chromatography and gas chromatography-mass spectrometry. Clin Chim Acta. 1975 Jun 20;61(3):247-56. [PubMed:1149252 ]
Drebing CJ, Freedman R, Waldo M, Gerhardt GA: Unconjugated methoxylated catecholamine metabolites in human saliva. Quantitation methodology and comparison with plasma levels. Biomed Chromatogr. 1989 Sep;3(5):217-20. [PubMed:2804429 ]
Bostrom B, Mirkin BL: Elevation of cerebrospinal fluid catecholamine metabolites in patients with intracranial tumors of neuroectodermal origin. J Clin Oncol. 1987 Jul;5(7):1090-7. [PubMed:3598613 ]
Afonso D, Castellanos MA, Rodriguez M: Determination of monoamines and indoles in amniotic fluid by high-performance liquid chromatography-electrochemical detection. J Chromatogr. 1990 Jun 8;528(1):101-9. [PubMed:1696583 ]
Djoumbou-Feunang Y, Fiamoncini J, Gil-de-la-Fuente A, Greiner R, Manach C, Wishart DS: BioTransformer: a comprehensive computational tool for small molecule metabolism prediction and metabolite identification. J Cheminform. 2019 Jan 5;11(1):2. doi: 10.1186/s13321-018-0324-5. [PubMed:30612223 ]

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
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.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

S-Adenosylmethionine + 3,4-Dihydroxymandelic acid → S-Adenosylhomocysteine + Vanillylmandelic acid	details

Enzyme Details

2. Aldehyde dehydrogenase, dimeric NADP-preferring

General function:: Involved in oxidoreductase activity
Specific function:: ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:: ALDH3A1
Uniprot ID:: P30838
Molecular weight:: 50394.57

Reactions

3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Ion	details
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Ion	details

Enzyme Details

3. Aldehyde dehydrogenase family 1 member A3

General function:: Involved in oxidoreductase activity
Specific function:: Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:: ALDH1A3
Uniprot ID:: P47895
Molecular weight:: 56107.995

Reactions

3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Ion	details
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Ion	details

Enzyme Details

4. Aldehyde dehydrogenase family 3 member B2

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: ALDH3B2
Uniprot ID:: P48448
Molecular weight:: 42623.62

Reactions

3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Ion	details
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Ion	details

Enzyme Details

5. Aldehyde dehydrogenase family 3 member B1

General function:: Involved in oxidoreductase activity
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. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:: ALDH3B1
Uniprot ID:: P43353
Molecular weight:: 51839.245

Reactions

3-Methoxy-4-hydroxyphenylglycolaldehyde + NAD + Water → Vanillylmandelic acid + NADH + Hydrogen Ion	details
3-Methoxy-4-hydroxyphenylglycolaldehyde + NADP + Water → Vanillylmandelic acid + NADPH + Hydrogen Ion	details

Showing metabocard for Vanillylmandelic acid (HMDB0000291)

MOL for HMDB0000291 (Vanillylmandelic acid)

3D MOL for HMDB0000291 (Vanillylmandelic acid)

3D SDF for HMDB0000291 (Vanillylmandelic acid)

3D-SDF for HMDB0000291 (Vanillylmandelic acid)

PDB for HMDB0000291 (Vanillylmandelic acid)

3D PDB for HMDB0000291 (Vanillylmandelic acid)

SMILES for HMDB0000291 (Vanillylmandelic acid)

INCHI for HMDB0000291 (Vanillylmandelic acid)

Structure for HMDB0000291 (Vanillylmandelic acid)

3D Structure for HMDB0000291 (Vanillylmandelic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

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