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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 17:15:45 UTC

HMDB ID

HMDB0001490

Secondary Accession Numbers

HMDB0002909
HMDB0006775
HMDB01490
HMDB02909
HMDB06775

Metabolite Identification

Common Name

Vanylglycol

Description

Vanylglycol, also known as 3-Methoxy-4-hydroxyphenylethyleneglycol (MHPG), 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. It is synthesized from endogenous epinephrine and norepinephrine in vivo. It is found in brain, blood, CSF, and urine, where its concentrations are used to measure catecholamine turnover. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. Vanylglycol and pyrocatechol can be biosynthesized from 3,4-dihydroxyphenylglycol and guaiacol; which is catalyzed by the enzyme catechol O-methyltransferase. Vanylglycol is a O-methylated metabolite of normetanephrine. In humans, vanylglycol is involved in the metabolic disorder called tyrosinemia in newborns. Alcohol consumption increases the level of vanylglycol in urine and CSF. Vanylglycol is found normally in urine, in plasma and cerebrospinal fluid. Outside of the human body, vanylglycol has been detected, but not quantified in several different foods, such as blackcurrants, chinese bayberries, elderberries, oriental wheats, and poppies.

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      20.601 -21.094   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.601 -22.634   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.935 -23.404   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.269 -22.634   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.269 -21.094   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.935 -20.324   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      19.268 -23.404   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      21.935 -24.944   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      20.601 -25.714   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.602 -20.324   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      24.602 -18.784   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      25.936 -21.094   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      27.270 -20.324   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    2                                                            
CONECT    8    3    9                                                       
CONECT    9    8                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(4-Hydroxy-3-methoxyphenyl)-1,2-ethanediol	HMDB
3-Methoxy-4-hydroxyphenethylene glycol	HMDB
3-Methoxy-4-hydroxyphenyl glycol	HMDB
4-Hydroxy-3-methoxy-b-phenylglycol	HMDB
4-Hydroxy-3-methoxy-beta-phenylglycol	HMDB
4-Hydroxy-3-methoxyphenyl glycol	HMDB
HMPG	HMDB
Hydroxymethoxyphenylglycol	HMDB, MeSH
Methoxyhydroxyphenylglycol	HMDB, MeSH
MHPG	HMDB, MeSH
MOPEG	HMDB, MeSH
4 Hydroxy 3 methoxyphenylethyleneglycol	MeSH, HMDB
4 Hydroxy 3 methoxyphenylglycol	MeSH, HMDB
4-Hydroxy-3-methoxyphenylethyleneglycol	MeSH, HMDB
Methoxyhydroxyphenylglycol, (-)-isomer	MeSH, HMDB
4 Hydroxy 3 methoxyphenylethylene glycol	MeSH, HMDB
4-Hydroxy-3-methoxyphenylglycol	MeSH, HMDB
Methoxyhydroxyphenylglycol, (+)-isomer	MeSH, HMDB
4-Hydroxy-3-methoxyphenylethylene glycol	MeSH, HMDB
Methoxyhydroxyphenylglycol, (+-)-isomer	MeSH, HMDB

Chemical Formula

C₉H₁₂O₄

Average Molecular Weight

184.1892

Monoisotopic Molecular Weight

184.073558872

IUPAC Name

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

Traditional Name

methoxyhydroxyphenylglycol

CAS Registry Number

534-82-7

SMILES

COC1=CC(=CC=C1O)C(O)CO

InChI Identifier

InChI=1S/C9H12O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,10-12H,5H2,1H3

InChI Key

FBWPWWWZWKPJFL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Secondary alcohol
1,2-diol
Ether
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:1576 )
methoxybenzene (CHEBI:1576 )
a guaiacol (CPD-11497 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.99 g/L	ALOGPS
logP	-0.13	ALOGPS
logP	0.11	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.28 m³·mol⁻¹	ChemAxon
Polarizability	18.64 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	141.677	31661259
DarkChem	[M-H]-	136.963	31661259
AllCCS	[M+H]+	141.25	32859911
AllCCS	[M-H]-	138.841	32859911
DeepCCS	[M+H]+	136.525	30932474
DeepCCS	[M-H]-	133.427	30932474
DeepCCS	[M-2H]-	170.224	30932474
DeepCCS	[M+Na]+	145.763	30932474
AllCCS	[M+H]+	141.2	32859911
AllCCS	[M+H-H2O]+	137.0	32859911
AllCCS	[M+NH4]+	145.2	32859911
AllCCS	[M+Na]+	146.3	32859911
AllCCS	[M-H]-	138.8	32859911
AllCCS	[M+Na-2H]-	139.8	32859911
AllCCS	[M+HCOO]-	140.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Vanylglycol	COC1=CC(=CC=C1O)C(O)CO	3143.3	Standard polar	33892256
Vanylglycol	COC1=CC(=CC=C1O)C(O)CO	1769.1	Standard non polar	33892256
Vanylglycol	COC1=CC(=CC=C1O)C(O)CO	1669.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vanylglycol,1TMS,isomer #1	COC1=CC(C(O)CO)=CC=C1O[Si](C)(C)C	1795.4	Semi standard non polar	33892256
Vanylglycol,1TMS,isomer #2	COC1=CC(C(CO)O[Si](C)(C)C)=CC=C1O	1744.7	Semi standard non polar	33892256
Vanylglycol,1TMS,isomer #3	COC1=CC(C(O)CO[Si](C)(C)C)=CC=C1O	1805.2	Semi standard non polar	33892256
Vanylglycol,2TMS,isomer #1	COC1=CC(C(CO)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1780.1	Semi standard non polar	33892256
Vanylglycol,2TMS,isomer #2	COC1=CC(C(O)CO[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1811.7	Semi standard non polar	33892256
Vanylglycol,2TMS,isomer #3	COC1=CC(C(CO[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O	1775.9	Semi standard non polar	33892256
Vanylglycol,3TMS,isomer #1	COC1=CC(C(CO[Si](C)(C)C)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1779.9	Semi standard non polar	33892256
Vanylglycol,1TBDMS,isomer #1	COC1=CC(C(O)CO)=CC=C1O[Si](C)(C)C(C)(C)C	2044.6	Semi standard non polar	33892256
Vanylglycol,1TBDMS,isomer #2	COC1=CC(C(CO)O[Si](C)(C)C(C)(C)C)=CC=C1O	2002.5	Semi standard non polar	33892256
Vanylglycol,1TBDMS,isomer #3	COC1=CC(C(O)CO[Si](C)(C)C(C)(C)C)=CC=C1O	2045.4	Semi standard non polar	33892256
Vanylglycol,2TBDMS,isomer #1	COC1=CC(C(CO)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2259.8	Semi standard non polar	33892256
Vanylglycol,2TBDMS,isomer #2	COC1=CC(C(O)CO[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2286.9	Semi standard non polar	33892256
Vanylglycol,2TBDMS,isomer #3	COC1=CC(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O	2254.0	Semi standard non polar	33892256
Vanylglycol,3TBDMS,isomer #1	COC1=CC(C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2470.1	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 - Vanylglycol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-2900000000-85ebe9a57a84ddca41b6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (3 TMS) - 70eV, Positive	splash10-0079-7149000000-54b71f18882477571deb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Vanylglycol 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 - Vanylglycol Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-0uxr-0900000000-fb2c82b5598c8c9bab3a	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vanylglycol Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-00di-0900000000-a449b185542d66dc0be8	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Vanylglycol Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-006x-9600000000-316d1194b9b0ed76d178	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 10V, Positive-QTOF	splash10-000i-0900000000-f104dd3883189a74b622	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 20V, Positive-QTOF	splash10-00kr-0900000000-040295df7423a417edab	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 40V, Positive-QTOF	splash10-0f72-3900000000-87310e73492350a05b5c	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 10V, Negative-QTOF	splash10-001i-0900000000-01cbe4fce361c48afabf	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 20V, Negative-QTOF	splash10-05ur-1900000000-b4ac6a118c11eb31a6ff	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 40V, Negative-QTOF	splash10-0a4i-5900000000-4a1c057f8cdd445e7125	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 10V, Positive-QTOF	splash10-004r-0900000000-df828b6c78ec969e404f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 20V, Positive-QTOF	splash10-056r-4900000000-97f0c28e2ac7713a8fc5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 40V, Positive-QTOF	splash10-0ue9-9100000000-ed2fd3623e179bd8e27f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 10V, Negative-QTOF	splash10-00lr-0900000000-9b55b059e2dc27b7380f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 20V, Negative-QTOF	splash10-0a4l-2900000000-44ed0b094433b8f04721	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vanylglycol 40V, Negative-QTOF	splash10-053u-6900000000-4de993e85915570061f3	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	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+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Brain
Platelet

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 and Quantified	0.017 +/- 0.004 uM	Adult (>18 years old)	Both	Normal	20206656	details
Blood	Detected and Quantified	0.0173 +/- 0.0034 uM	Adult (>18 years old)	Both	Normal	2480613	details
Blood	Detected and Quantified	0.025 +/- 0.005 uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.057 +/- 0.04 uM	Adult (>18 years old)	Not Specified	Normal	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.075 +/- 0.037 uM	Children (1-13 years old)	Both	Normal	9732974	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.036 +/- 0.008 uM	Adult (>18 years old)	Not Specified	Normal	1712114	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.010 +/- 0.003 uM	Adult (>18 years old)	Not Specified	Normal	6085084	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.082 (0.051-0.112) uM	Infant (0-1 year old)	Not Specified	Normal	16288991	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.050 (0.039-0.061) uM	Adult (>18 years old)	Both	Normal	9116178	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	38.1 +/- 7.2 uM	Adult (>18 years old)	Both	Normal	1694425	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.042 +/- 0.005 uM	Adult (>18 years old)	Female	Normal	6198473	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	42.1 +/- 4.9 uM	Adult (>18 years old)	Female	Normal	2415198	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.05 (0.0058-0.094) uM	Adult (>18 years old)	Both	Normal	16259647	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.116 +/- 0.16 uM	Infant (0-1 year old)	Both	Normal	9732974	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.054 +/- 0.014 uM	Children (1-13 years old)	Both	Normal	9732974	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.044 +/- 0.020 uM	Adolescent (13-18 years old)	Both	Normal	9732974	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.032-0.068 uM	Children (1-13 years old)	Male	Normal	18502672	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.037-0.075 uM	Children (1-13 years old)	Male	Normal	18502672	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.07 +/- 0.040 uM	Infant (0-1 year old)	Both	Normal	9732974	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.17 +/- 0.095 uM	Adolescent (13-18 years old)	Both	Normal	9732974	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.039 (0.047-0.081) uM	Adult (>18 years old)	Both	Normal	15557528	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.082 (0.051-0.11) uM	Adult (>18 years old)	Both	Normal	16288991	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.066 +/- 0.038 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0338 +/- 0.0091 uM	Not Specified	Not Specified	Normal	7887134	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.05 +/- 0.032 uM	Adult (>18 years old)	Not Specified	Normal	1705463	details
Urine	Detected and Quantified	0.1-2.1 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	8503438	details
Urine	Detected and Quantified	0.06 +/- 0.06 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected and Quantified	0.045 +/- 0.0039 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	6403958	details
Urine	Detected and Quantified	0.049 +/- 0.0075 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	6403958	details
Urine	Detected and Quantified	0.66 +/- 0.04 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.86 +/- 0.26 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.021 +/- 0.007 uM	Adult (>18 years old)	Both	Schizophrenia	20206656	details
Blood	Detected and Quantified	0.0237 +/- 0.011 uM	Adult (>18 years old)	Male	Schizophrenia	2480613	details
Blood	Detected and Quantified	0.0232 +/- 0.0063 uM	Adult (>18 years old)	Both	Schizophrenia	2480613	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.041 +/- 0.023 uM	Adult (>18 years old)	Not Specified	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.064 +/- 0.045 uM	Adult (>18 years old)	Not Specified	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.037 +/- 0.006 uM	Adult (>18 years old)	Not Specified	Panic Disorder	1712114	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.042 +/- 0.002 uM	Adult (>18 years old)	Not Specified	Olivopontocerebellar atrophy (OPCA)	11383938	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.036 +/- 0.005 uM	Adult (>18 years old)	Not Specified	Autosomal recessive spastic ataxia of Charlevoix-Saguena	11383938	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.013 (0.012-0.014) uM	Children (1-13 years old)	Male	sepiapterin reductase deficiency	18502672	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.003 (0.000-0.005) uM	Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	16288991	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.044 (0.032-0.056) uM	Adult (>18 years old)	Both	Vascular Dementia	9116178	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	42.5 +/- 7.6 uM	Adult (>18 years old)	Both	Schizophrenia	1694425	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.039 (0.027-0.051) uM	Adult (>18 years old)	Both	Vascular dementia	9116178	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.044 (0.035-0.053) uM	Adult (>18 years old)	Both	Vascular Dementia	9116178	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	50.3 +/- 7.4 uM	Adult (>18 years old)	Female	Schizophrenia	2415198	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.048 (0.035-0.061) uM	Adult (>18 years old)	Both	Severe vascular dementia	9116178	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.09 +/- 0.09 uM	Adult (>18 years old)	Both	Major depression	9004051	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.042 +/- 0.0022 uM	Not Specified	Not Specified	Friedreich's ataxia	11383938	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0039 uM	Adult (>18 years old)	Both	Early-onset encephalopathy and cortical myoclonus (MECP2 gene mutation)	15557528	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.003 +/- 0.003 uM	Adult (>18 years old)	Both	Aromatic L-amino acid decarboxylase deficiency	16288991	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.012 uM	Adult (>18 years old)	Not Specified	Progressive cognitive impairment	1695809	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.05 +/- 0.002 uM	Adult (>18 years old)	Female	Schizophrenia	115032	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.04 +/- 0.002 uM	Adult (>18 years old)	Female	Schizophrenia	115032	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.051 +/- 0.0054 uM	Adult (>18 years old)	Not Specified	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.05 +/- 0.018 uM	Adult (>18 years old)	Not Specified	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0332 +/- 0.00622 uM	Adult (>18 years old)	Not Specified	Parkinson's Disease	7887134	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.048 +/- 0.033 uM	Adult (>18 years old)	Not Specified	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.046 +/- 0.021 uM	Adult (>18 years old)	Not Specified	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.046 +/- 0.029 uM	Adult (>18 years old)	Not Specified	Epilepsy	1705463	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.045 +/- 0.026 uM	Adult (>18 years old)	Not Specified	Epilepsy	1705463	details
Urine	Detected and Quantified	0.1-0.2 umol/mmol creatinine	Adult (>18 years old)	Male	Brunner Syndrome	8503438	details

Associated Disorders and Diseases

Disease References

Multi-infarct dementia
Wallin A, Blennow K, Edman A, Mansson JE: Decreased lumbar cerebrospinal fluid levels of monoamine metabolites in vascular dementia. Int Psychogeriatr. 1996 Fall;8(3):425-36. [PubMed:9116178 ]
Cortical myoclonus
Leuzzi V, Di Sabato ML, Zollino M, Montanaro ML, Seri S: Early-onset encephalopathy and cortical myoclonus in a boy with MECP2 gene mutation. Neurology. 2004 Nov 23;63(10):1968-70. [PubMed:15557528 ]
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 ]
Cognitive disorders
Hildebrand J, Bourgeois F, Buyse M, Przedborski S, Goldman S: Reproducibility of monoamine metabolite measurements in human cerebrospinal fluid. Acta Neurol Scand. 1990 May;81(5):427-30. [PubMed:1695809 ]
Schizophrenia
Harnryd C, Bjerkenstedt L, Grimm VE, Sedvall G: Reduction of MOPEG levels in cerebrospinal fluid of psychotic women after electroconvulsive treatment. Psychopharmacology (Berl). 1979 Aug 8;64(2):131-4. [PubMed:115032 ] Alfredsson G, Wiesel FA: Monoamine metabolites and amino acids in serum from schizophrenic patients before and during sulpiride treatment. Psychopharmacology (Berl). 1989;99(3):322-7. [PubMed:2480613 ] Pickar D, Breier A, Hsiao JK, Doran AR, Wolkowitz OM, Pato CN, Konicki PE, Potter WZ: Cerebrospinal fluid and plasma monoamine metabolites and their relation to psychosis. Implications for regional brain dysfunction in schizophrenia. Arch Gen Psychiatry. 1990 Jul;47(7):641-8. [PubMed:1694425 ] Bjerkenstedt L, Edman G, Hagenfeldt L, Sedvall G, Wiesel FA: Plasma amino acids in relation to cerebrospinal fluid monoamine metabolites in schizophrenic patients and healthy controls. Br J Psychiatry. 1985 Sep;147:276-82. [PubMed:2415198 ] Zumarraga M, Davila R, Basterreche N, Arrue A, Goienetxea B, Zamalloa MI, Erkoreka L, Bustamante S, Inchausti L, Gonzalez-Torres MA, Guimon J: Catechol O-methyltransferase and monoamine oxidase A genotypes, and plasma catecholamine metabolites in bipolar and schizophrenic patients. Neurochem Int. 2010 May-Jun;56(6-7):774-9. doi: 10.1016/j.neuint.2010.02.015. Epub 2010 Mar 4. [PubMed:20206656 ]
Epilepsy
Botez MI, Young SN: Effects of anticonvulsant treatment and low levels of folate and thiamine on amine metabolites in cerebrospinal fluid. Brain. 1991 Feb;114 ( Pt 1A):333-48. [PubMed:1705463 ]
Panic disorder
Eriksson E, Westberg P, Alling C, Thuresson K, Modigh K: Cerebrospinal fluid levels of monoamine metabolites in panic disorder. Psychiatry Res. 1991 Mar;36(3):243-51. [PubMed:1712114 ]
Olivopontocerebral atrophy
Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Hereditary spastic paraplegia
Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Friedreich's ataxia
Botez MI, Young SN: Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias. Can J Neurol Sci. 2001 May;28(2):134-40. [PubMed:11383938 ]
Major depressive disorder
Sheline Y, Bardgett ME, Csernansky JG: Correlated reductions in cerebrospinal fluid 5-HIAA and MHPG concentrations after treatment with selective serotonin reuptake inhibitors. J Clin Psychopharmacol. 1997 Feb;17(1):11-4. [PubMed:9004051 ]
Sepiapterin reductase deficiency
Verbeek MM, Willemsen MA, Wevers RA, Lagerwerf AJ, Abeling NG, Blau N, Thony B, Vargiami E, Zafeiriou DI: Two Greek siblings with sepiapterin reductase deficiency. Mol Genet Metab. 2008 Aug;94(4):403-9. doi: 10.1016/j.ymgme.2008.04.003. Epub 2008 May 27. [PubMed:18502672 ]
Parkinson's disease
Dizdar N, Kagedal B, Lindvall B: Treatment of Parkinson's disease with NADH. Acta Neurol Scand. 1994 Nov;90(5):345-7. [PubMed:7887134 ]
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

608643 (Aromatic L-amino acid decarboxylase deficiency)
181500 (Schizophrenia)
167870 (Panic disorder)
182601 (Hereditary spastic paraplegia)
229300 (Friedreich's ataxia)
608516 (Major depressive disorder)
182125 (Sepiapterin reductase deficiency)
168600 (Parkinson's disease)
300615 (Brunner Syndrome)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022651

KNApSAcK ID

Not Available

Chemspider ID

10348

KEGG Compound ID

C05594

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000330

Good Scents ID

Not Available

References

Synthesis Reference

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

Material Safety Data Sheet (MSDS)

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General References

Sjoberg S, Eriksson M, Nordin C: L-thyroxine treatment and neurotransmitter levels in the cerebrospinal fluid of hypothyroid patients: a pilot study. Eur J Endocrinol. 1998 Nov;139(5):493-7. [PubMed:9849813 ]
Eklundh T, Eriksson M, Sjoberg S, Nordin C: Monoamine precursors, transmitters and metabolites in cerebrospinal fluid: a prospective study in healthy male subjects. J Psychiatr Res. 1996 May-Jun;30(3):201-8. [PubMed:8884658 ]
Javors MA, Bowden CL, Maas JW: 3-methoxy-4-hydroxyphenylglycol, 5-hydroxyindoleacetic acid, and homovanillic acid in human cerebrospinal fluid. Storage and measurement by reversed-phase high-performance liquid chromatography and coulometric detection using 3-methoxy-4-hydroxyphenyllactic acid as an internal standard. J Chromatogr. 1984 Dec 12;336(2):259-69. [PubMed:6085084 ]
Eriksson E, Westberg P, Alling C, Thuresson K, Modigh K: Cerebrospinal fluid levels of monoamine metabolites in panic disorder. Psychiatry Res. 1991 Mar;36(3):243-51. [PubMed:1712114 ]
Sullivan GM, Oquendo MA, Huang YY, Mann JJ: Elevated cerebrospinal fluid 5-hydroxyindoleacetic acid levels in women with comorbid depression and panic disorder. Int J Neuropsychopharmacol. 2006 Oct;9(5):547-56. Epub 2005 Nov 1. [PubMed:16259647 ]
von Holst H, Lindquist C, Sedvall G: Increased concentrations of the monoamine metabolites homovanillic acid and 5-hydroxyindoleacetic acid in lumbar and central CSF and of 3-methoxy-4-hydroxyphenylglycol in lumbar CSF after subarachnoid haemorrhage. Acta Neurochir (Wien). 1985;77(3-4):146-51. [PubMed:2416192 ]
Harnryd C, Bjerkenstedt L, Grimm VE, Sedvall G: Reduction of MOPEG levels in cerebrospinal fluid of psychotic women after electroconvulsive treatment. Psychopharmacology (Berl). 1979 Aug 8;64(2):131-4. [PubMed:115032 ]
Brautigam C, Wevers RA, Jansen RJ, Smeitink JA, de Rijk-van Andel JF, Gabreels FJ, Hoffmann GF: Biochemical hallmarks of tyrosine hydroxylase deficiency. Clin Chem. 1998 Sep;44(9):1897-904. [PubMed:9732974 ]
Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [PubMed:6198473 ]
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 ]
Frankenhaeuser M, Lundberg U, Rauste von Wright M, von Wright J, Sedvall G: Urinary monoamine metabolites as indices of mental stress in healthy males and females. Pharmacol Biochem Behav. 1986 Jun;24(6):1521-5. [PubMed:2426718 ]
Leuzzi V, Di Sabato ML, Zollino M, Montanaro ML, Seri S: Early-onset encephalopathy and cortical myoclonus in a boy with MECP2 gene mutation. Neurology. 2004 Nov 23;63(10):1968-70. [PubMed:15557528 ]
Wallin A, Blennow K, Edman A, Mansson JE: Decreased lumbar cerebrospinal fluid levels of monoamine metabolites in vascular dementia. Int Psychogeriatr. 1996 Fall;8(3):425-36. [PubMed:9116178 ]
Kawamura M, Eisenhofer G, Kopin IJ, Kador PF, Lee YS, Fujisawa S, Sato S: Aldose reductase: an aldehyde scavenging enzyme in the intraneuronal metabolism of norepinephrine in human sympathetic ganglia. Auton Neurosci. 2002 Mar 18;96(2):131-9. [PubMed:11958479 ]
Evangelou AM, Malamas MP, Vezyraki P, Karkabounas SC: Is epinephrine-induced platelet aggregation autoregulated by its metabolic degradation products in vivo? In Vivo. 1998 May-Jun;12(3):321-5. [PubMed:9706478 ]
Rollag J, Liu T, Hage DS: Determination of 3-methoxy-4-hydroxyphenylethylene glycol in urine using reversed-phase liquid chromatography with column switching and electrochemical detection. J Chromatogr B Biomed Appl. 1995 Jan 20;663(2):193-200. [PubMed:7735466 ]
Brewerton TD, Berrettini WH, Nurnberger JI Jr, Linnoila M: Analysis of seasonal fluctuations of CSF monoamine metabolites and neuropeptides in normal controls: findings with 5HIAA and HVA. Psychiatry Res. 1988 Mar;23(3):257-65. [PubMed:2455302 ]

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-Dihydroxyphenylglycol → S-Adenosylhomocysteine + Vanylglycol	details

Showing metabocard for Vanylglycol (HMDB0001490)

MOL for HMDB0001490 (Vanylglycol)

3D MOL for HMDB0001490 (Vanylglycol)

3D SDF for HMDB0001490 (Vanylglycol)

3D-SDF for HMDB0001490 (Vanylglycol)

PDB for HMDB0001490 (Vanylglycol)

3D PDB for HMDB0001490 (Vanylglycol)

SMILES for HMDB0001490 (Vanylglycol)

INCHI for HMDB0001490 (Vanylglycol)

Structure for HMDB0001490 (Vanylglycol)

3D Structure for HMDB0001490 (Vanylglycol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions