MiMeDB: Showing metabocard for Vanillylmandelic acid (MMDBc0000511)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:39:26 UTC

Update Date

2024-04-30 19:32:43 UTC

Metabolite ID

MMDBc0000511

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>
MMDBc0000511

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₉H₁₀O₅

Average Mass

198.1727

Monoisotopic Mass

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

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-3900000000-97b85fd5a9736a5d5eb0	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-009t-7396100000-b5450c24921a68f5f6b3	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000b-0900000000-1e2dedd8e81249787b29	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000i-0900000000-3d2cd918dc6b76dfba3f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000i-2900000000-b543807e43e5091abb53	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1900000000-1c88ce4d32680e3379de	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-30e1c8cb4fa5443c687e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-c4c762f850d22fee6281	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-0900000000-1308d37a2313f5479365	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fmj-0900000000-bcdff30bcec2389ffef6	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-3900000000-cd2db271b5a0926adfeb	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00dj-9700000000-2c212037a037fcd229d0	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kg9-1900000000-81b2ab77bf3382c9f5de	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-4900000000-e3b77a4d29235649ecce	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f8a-0900000000-04d80bfab4984d07e479	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-23d4830296b7ea07f0d5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fki-5900000000-9b9364530caece4b6c12	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f7t-0900000000-ac32d971a0581e8b6cb6	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-bce2f2854f319781df10	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0umi-9700000000-311af8dc825e2dd02614	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adrenal Gland
Blood
Epidermis
Feces
Saliva
Thyroid Gland
Urine

Tissue Locations

Adrenal Gland
Epidermis
Thyroid Gland

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191942	Catechol O-methyltransferase	Unknown	P21964	Homo sapiens
MMDBp0191962	Aldehyde dehydrogenase, dimeric NADP-preferring	Unknown	P30838	Homo sapiens
MMDBp0191964	Aldehyde dehydrogenase family 1 member A3	Unknown	P47895	Homo sapiens
MMDBp0192188	Aldehyde dehydrogenase family 3 member B2	Unknown	P48448	Homo sapiens
MMDBp0192189	Aldehyde dehydrogenase family 3 member B1	Unknown	P43353	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000076	3-Methoxy-4-hydroxyphenylglycolaldehyde	Vanillylmandelic acid	Aldehyde dehydrogenase 1 family, member a3	3-Methoxy-4-Hydroxyphenylglycolaldehyde:NAD+ Oxidoreductase	VMH	30371894
MMDBr0000077	3-Methoxy-4-hydroxyphenylglycolaldehyde	Vanillylmandelic acid	Aldehyde dehydrogenase 1 family, member a3	3-Methoxy-4-Hydroxyphenylglycolaldehyde:NADP+ Oxidoreductase	VMH	30371894
MMDBr0002701	3-Methoxy-4-hydroxyphenylglycolaldehyde	Vanillylmandelic acid	Aldehyde dehydrogenase 1 family, member a3	3-Methoxy-4-Hydroxyphenylglycolaldehyde:NAD+ Oxidoreductase Tyrosine Metabolism	VMH	17379813 18621017
MMDBr0002702	3-Methoxy-4-hydroxyphenylglycolaldehyde	Vanillylmandelic acid	Aldehyde dehydrogenase 1 family, member a3	3-Methoxy-4-Hydroxyphenylglycolaldehyde:NADP+ Oxidoreductase Tyrosine Metabolism	VMH	17379813 18621017
MMDBr0008541	Vanillylmandelic acid	Vanillylmandelic acid	Not Available	Transport of 3-Methoxy-4-Hydroxymandelate, Mitochondrial	VMH	30371894
MMDBr0008542	Vanillylmandelic acid	Vanillylmandelic acid	Not Available	Transport 3-Methoxy-4-Hydroxymandelate, Extracellular	VMH	30371894
MMDBr0010410	3,4-Dihydroxymandelic acid	Vanillylmandelic acid	Catechol-o-methyltransferase	Catechol O-Methyltransferase	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Aromatic l-amino acid decarboxylase deficiency		Association	Human Urine	HMDB	9686366
Aromatic l-amino acid decarboxylase deficiency		Association	Human Urine	HMDB	16288991
Phenylketonuria		Association	Human Urine	HMDB	4837567
Eosinophilic esophagitis		Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Eosinophilic esophagitis	Slight Increase	Association	Human Urine	HMDB	Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	0.5				umol/mmol creatinine	Children (1-13 years old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human Urine	Detected and Quantified	0.9				umol/mmol creatinine	Infant (0-1 year old)	Female	Aromatic L-amino acid decarboxylase deficiency	HMDB	9686366
Human 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	HMDB	16288991
Human Urine	Detected and Quantified			0.2	0.4	umol/mmol creatinine	Adult (>18 years old)	Male	Brunner Syndrome	HMDB	8503438
Human Urine	Detected and Quantified	15.404	14.833			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified	4.564	1.369			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified	9.128	4.450			umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	HMDB	4837567
Human Urine	Detected and Quantified	6.2				umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	21670092
Human Urine	Detected and Quantified			0.300	19.700	umol/mmol creatinine	Children (1-13 years old)	Female	Normal	HMDB	9686366
Human Urine	Detected and Quantified			0.5	7.6	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	8503438
Human Urine	Detected and Quantified			1.1	1.7	umol/mmol creatinine	Adult (>18 years old)	Male	Normal	HMDB	27012787
Human Urine	Detected and Quantified	1.2	0.5			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	15992788
Human Urine	Detected and Quantified	1.585	1.095			umol/mmol creatinine	Adult (>18 years old)	Both		HMDB	9439441
Human Urine	Detected and Quantified	1.6		0.6	2.8	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			1.6	2.2	umol/mmol creatinine	Adult (>18 years old)	Female	Normal	HMDB	27012787
Human Urine	Detected and Quantified	10.0		0.3	20.0	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	16288991
Human Urine	Detected and Quantified	12.4		11.6	25.9	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	12.5		3.7	21.8	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	13.24	5.3			umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	HMDB	24296288
Human Urine	Detected and Quantified	2.3		1.0	3.4	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			3.22	9.08	umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	24769278
Human Urine	Detected and Quantified	3.67	2.12			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human Urine	Detected and Quantified	4.18	1.55			umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	24556394
Human Urine	Detected and Quantified	4.906	1.769			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	5.0776	1.712			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	5.135	1.826			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	4837567
Human Urine	Detected and Quantified	5.2		2.5	16.1	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	5.38	1.83			umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	HMDB	24296288
Human Urine	Detected and Quantified	5.68	2.19			umol/mmol creatinine	Infant (6 months - <1 year old)	Both	Normal	HMDB	24769278
Human Urine	Detected and Quantified	6.19	2.014			umol/mmol creatinine	Infant (1 - 6 months old)	Both	Normal	HMDB	24769278
Human Urine	Detected and Quantified	6.22	2.32			umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	HMDB	24769278
Human Urine	Detected and Quantified	6.5		1.3	11.5	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	6.5		2.9	13.0	umol/mmol creatinine	Children (1-13 years old)	Both	Normal	HMDB	8087979
Human Urine	Detected and Quantified	6.869	2.756			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	7.586	3.852			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	5.93	3.016			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Urine	Detected and Quantified	7.758	2.944			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	HMDB	Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work)
Human Blood	Detected and Quantified	0.035	0.008			uM	Adult (>18 years old)	Male	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	<=3.289				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Merck Manual of Diagnosis and Therapy.
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Thyroid gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	9439441
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

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

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/0009-8981(77)90010-9. [PubMed:589798 ]
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. doi: 10.1126/science.635588. [PubMed:635588 ]
Dias PL, Amarasiri AA: 4-hydroxy-3-methoxymandelic acid (HMMA) excretion in retinoblastoma. Br J Ophthalmol. 1978 Aug;62(8):525-7. doi: 10.1136/bjo.62.8.525. [PubMed:687548 ]
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. doi: 10.1016/0009-8981(75)90414-3. [PubMed:1149252 ]
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. doi: 10.1126/science.1257763. [PubMed:1257763 ]
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. doi: 10.1016/s0378-4347(00)82366-x. [PubMed:1696583 ]
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. doi: 10.1002/bmc.1130030509. [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. doi: 10.1200/JCO.1987.5.7.1090. [PubMed:3598613 ]
Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
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. doi: 10.1007/BF00445797. [PubMed:6394335 ]
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 ]
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 ]
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 ]
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. doi: 10.1046/j.1526-4610.1997.3704211.x. [PubMed:9150615 ]
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. doi: 10.1124/jpet.103.049270. Epub 2003 Mar 20. [PubMed:12649306 ]
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 ]

Showing metabocard for Vanillylmandelic acid (MMDBc0000511)

MOL for #<Metabolite:0x00007fa4dd12d5e8>

3D MOL for #<Metabolite:0x00007fa4dd12d5e8>

3D SDF for #<Metabolite:0x00007fa4dd12d5e8>

3D-SDF for #<Metabolite:0x00007fa4dd12d5e8>

PDB for #<Metabolite:0x00007fa4dd12d5e8>

3D PDB for #<Metabolite:0x00007fa4dd12d5e8>

SMILES for #<Metabolite:0x00007fa4dd12d5e8>

INCHI for #<Metabolite:0x00007fa4dd12d5e8>

Structure for #<Metabolite:0x00007fa4dd12d5e8>

3D Structure for #<Metabolite:0x00007fa4dd12d5e8>