MiMeDB: Showing metabocard for Homovanillyl alcohol (MMDBc0033654)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:57:36 UTC

Update Date

2022-08-31 22:37:29 UTC

Metabolite ID

MMDBc0033654

Metabolite Identification

Common Name

Homovanillyl alcohol

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                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    7                                                       
CONECT    3    2    8                                                       
CONECT    4    5    7                                                       
CONECT    5    4   10                                                       
CONECT    6    7    9                                                       
CONECT    7    2    4    6                                                  
CONECT    8    3    9   11                                                  
CONECT    9    6    8   12                                                  
CONECT   10    5                                                            
CONECT   11    8                                                            
CONECT   12    1    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
2-(4-Guaiacyl)-ethanol	HMDB
2-(4-Hydroxy-3-methoxyphenyl)-ethanol	HMDB
3-Methoxy-4-hydroxyphenylethanol	HMDB, MeSH
4-(2-Hydroxyethyl)-2-methoxyphenol	HMDB
4-(2-Hydroxyethyl)guaiacol	HMDB
4-Hydroxy-3-methoxy-benzeneethanol	HMDB
4-Hydroxy-3-methoxybenzeneethanol	HMDB
4-Hydroxy-3-methoxyphenethanol	HMDB
4-Hydroxy-3-methoxyphenethyl alcohol	HMDB
4-Hydroxy-3-methoxyphenylethyl alcohol	HMDB
Guaiacyl ethanol	HMDB
Homovanilline alcohol	HMDB
Homovanillyl alcohol	HMDB
Alcohol, hydroxymethoxyphenethyl	MeSH
3 Methoxy 4 hydroxyphenylethanol	MeSH
Hydroxymethoxyphenethyl alcohol	MeSH
MHPE	MeSH
MOPET	MeSH
Methoxyhydroxyphenylethanol	MeSH

Molecular Formula

C₉H₁₂O₃

Average Mass

168.1898

Monoisotopic Mass

168.07864425

IUPAC Name

4-(2-hydroxyethyl)-2-methoxyphenol

Traditional Name

homovanillyl alcohol

CAS Registry Number

498-00-0

SMILES

COC1=C(O)C=CC(CCO)=C1

InChI Identifier

InChI=1S/C9H12O3/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,10-11H,4-5H2,1H3

InChI Key

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	11.6 g/L	ALOGPS
logP	0.95	ALOGPS
logP	1.03	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	10.19	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.07 m³·mol⁻¹	ChemAxon
Polarizability	17.67 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

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Brain
Cerebrospinal Fluid (CSF)
Platelet
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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 Cerebrospinal Fluid (CSF)	HMDB	16288991
Cortical myoclonus	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	15557528
Epilepsy	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	1705463
Friedreich's ataxia	Slight Increase	Association	Human Cerebrospinal Fluid (CSF)	HMDB	11383938
Hereditary spastic paraplegia	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	11383938
Major depressive disorder	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	9004051
Multi-infarct dementia	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	9116178
Olivopontocerebral atrophy	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	11383938
Panic disorder	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	1712114
Parkinson's disease		Association	Human Cerebrospinal Fluid (CSF)	HMDB	7887134
Schizophrenia	Slight Increase	Association	Human Blood	HMDB	20206656
Schizophrenia	Slight Increase	Association	Human Blood	HMDB	2480613
Schizophrenia	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	115032
Schizophrenia	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	1694425
Schizophrenia	Increased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	2415198
Sepiapterin reductase deficiency	Decreased	Association	Human Cerebrospinal Fluid (CSF)	HMDB	18502672

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	2	Human feces	Unknown

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	0.003		0.000	0.005	Infant (0-1 year old)	Male	Aromatic L-amino acid decarboxylase deficiency	HMDB	16288991
Human	Detected and Quantified	0.003	0.003			Adult (>18 years old)	Both	Aromatic L-amino acid decarboxylase deficiency	HMDB	16288991
Human	Detected and Quantified			0.1	0.2	Adult (>18 years old)	Male	Brunner Syndrome	HMDB	8503438
Human	Detected and Quantified	0.012				Adult (>18 years old)	Not Specified	Progressive cognitive impairment	HMDB	1695809
Human	Detected and Quantified	0.0039				Adult (>18 years old)	Both	Early-onset encephalopathy and cortical myoclonus (MECP2 gene mutation)	HMDB	15557528
Human	Detected and Quantified	0.041	0.023			Adult (>18 years old)	Not Specified	Epilepsy	HMDB	1705463
Human	Detected and Quantified	0.045	0.026			Adult (>18 years old)	Not Specified	Epilepsy	HMDB	1705463
Human	Detected and Quantified	0.046	0.021			Adult (>18 years old)	Not Specified	Epilepsy	HMDB	1705463
Human	Detected and Quantified	0.046	0.029			Adult (>18 years old)	Not Specified	Epilepsy	HMDB	1705463
Human	Detected and Quantified	0.048	0.033			Adult (>18 years old)	Not Specified	Epilepsy	HMDB	1705463
Human	Detected and Quantified	0.05	0.018			Adult (>18 years old)	Not Specified	Epilepsy	HMDB	1705463
Human	Detected and Quantified	0.051	0.0054			Adult (>18 years old)	Not Specified	Epilepsy	HMDB	1705463
Human	Detected and Quantified	0.064	0.045			Adult (>18 years old)	Not Specified	Epilepsy	HMDB	1705463
Human	Detected and Quantified	0.042	0.0022			Not Specified	Not Specified	Friedreich's ataxia	HMDB	11383938
Human	Detected and Quantified	0.036	0.005			Adult (>18 years old)	Not Specified	Autosomal recessive spastic ataxia of Charlevoix-Saguena	HMDB	11383938
Human	Detected and Quantified	0.09	0.09			Adult (>18 years old)	Both	Major depression	HMDB	9004051
Human	Detected and Quantified	0.039		0.027	0.051	Adult (>18 years old)	Both	Vascular dementia	HMDB	9116178
Human	Detected and Quantified	0.044		0.032	0.056	Adult (>18 years old)	Both	Vascular Dementia	HMDB	9116178
Human	Detected and Quantified	0.044		0.035	0.053	Adult (>18 years old)	Both	Vascular Dementia	HMDB	9116178
Human	Detected and Quantified	0.048		0.035	0.061	Adult (>18 years old)	Both	Severe vascular dementia	HMDB	9116178
Human	Detected and Quantified	0.042	0.002			Adult (>18 years old)	Not Specified	Olivopontocerebellar atrophy (OPCA)	HMDB	11383938
Human	Detected and Quantified	0.037	0.006			Adult (>18 years old)	Not Specified	Panic Disorder	HMDB	1712114
Human	Detected and Quantified	0.0332	0.00622			Adult (>18 years old)	Not Specified	Parkinson's Disease	HMDB	7887134
Human	Detected and Quantified	0.021	0.007			Adult (>18 years old)	Both	Schizophrenia	HMDB	20206656
Human	Detected and Quantified	0.0232	0.0063			Adult (>18 years old)	Both	Schizophrenia	HMDB	2480613
Human	Detected and Quantified	0.0237	0.011			Adult (>18 years old)	Male	Schizophrenia	HMDB	2480613
Human	Detected and Quantified	0.04	0.002			Adult (>18 years old)	Female	Schizophrenia	HMDB	115032
Human	Detected and Quantified	0.05	0.002			Adult (>18 years old)	Female	Schizophrenia	HMDB	115032
Human	Detected and Quantified	42.5	7.6			Adult (>18 years old)	Both	Schizophrenia	HMDB	1694425
Human	Detected and Quantified	50.3	7.4			Adult (>18 years old)	Female	Schizophrenia	HMDB	2415198
Human	Detected and Quantified	0.013		0.012	0.014	Children (1-13 years old)	Male	sepiapterin reductase deficiency	HMDB	18502672
Human	Detected and Quantified	0.010	0.003			Adult (>18 years old)	Not Specified	Normal	HMDB	6085084
Human	Detected and Quantified	0.017	0.004			Adult (>18 years old)	Both	Normal	HMDB	20206656
Human	Detected and Quantified	0.0173	0.0034			Adult (>18 years old)	Both	Normal	HMDB	2480613
Human	Detected and Quantified			0.032	0.068	Children (1-13 years old)	Male	Normal	HMDB	18502672
Human	Detected and Quantified	0.0338	0.0091			Not Specified	Not Specified	Normal	HMDB	7887134
Human	Detected and Quantified	0.036	0.008			Adult (>18 years old)	Not Specified	Normal	HMDB	1712114
Human	Detected and Quantified			0.037	0.075	Children (1-13 years old)	Male	Normal	HMDB	18502672
Human	Detected and Quantified	0.039		0.047	0.081	Adult (>18 years old)	Both	Normal	HMDB	15557528
Human	Detected and Quantified	0.042	0.005			Adult (>18 years old)	Female	Normal	HMDB	6198473
Human	Detected and Quantified	0.044	0.020			Adolescent (13-18 years old)	Both	Normal	HMDB	9732974
Human	Detected and Quantified	0.045	0.0039			Adult (>18 years old)	Male	Normal	HMDB	6403958
Human	Detected and Quantified	0.049	0.0075			Adult (>18 years old)	Female	Normal	HMDB	6403958
Human	Detected and Quantified	0.05		0.0058	0.094	Adult (>18 years old)	Both	Normal	HMDB	16259647
Human	Detected and Quantified	0.05	0.032			Adult (>18 years old)	Not Specified	Normal	HMDB	1705463
Human	Detected and Quantified	0.050		0.039	0.061	Adult (>18 years old)	Both	Normal	HMDB	9116178
Human	Detected and Quantified	0.054	0.014			Children (1-13 years old)	Both	Normal	HMDB	9732974
Human	Detected and Quantified	0.057	0.04			Adult (>18 years old)	Not Specified	Normal	HMDB	1705463
Human	Detected and Quantified	0.06	0.06			Infant (0-1 year old)	Both	Normal	HMDB	2026685
Human	Detected and Quantified	0.07	0.040			Infant (0-1 year old)	Both	Normal	HMDB	9732974
Human	Detected and Quantified	0.075	0.037			Children (1-13 years old)	Both	Normal	HMDB	9732974
Human	Detected and Quantified	0.082		0.051	0.11	Adult (>18 years old)	Both	Normal	HMDB	16288991
Human	Detected and Quantified	0.082		0.051	0.112	Infant (0-1 year old)	Not Specified	Normal	HMDB	16288991
Human	Detected and Quantified			0.1	2.1	Adult (>18 years old)	Male	Normal	HMDB	8503438
Human	Detected and Quantified	0.116	0.16			Infant (0-1 year old)	Both	Normal	HMDB	9732974
Human	Detected and Quantified	0.17	0.095			Adolescent (13-18 years old)	Both	Normal	HMDB	9732974
Human	Detected and Quantified	38.1	7.2			Adult (>18 years old)	Both	Normal	HMDB	1694425
Human	Detected and Quantified	42.1	4.9			Adult (>18 years old)	Female	Normal	HMDB	2415198
Human	Detected and Quantified	0.025	0.005			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	Detected and Quantified	0.066	0.038			Adult (>18 years old)	Both	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	Detected and Quantified	0.66	0.04			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	Detected and Quantified	0.86	0.26			Adult (>18 years old)	Both	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 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
Human Brain	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified					Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0038925

DrugBank ID

Not Available

Phenol Explorer Compound ID

643

FooDB ID

FDB018391

KNApSAcK ID

Not Available

Chemspider ID

16039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16928

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

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. doi: 10.1007/BF00496052. [PubMed:115032 ]
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. doi: 10.1016/0165-1781(91)90023-i. [PubMed:1712114 ]
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. doi: 10.1007/BF01476218. [PubMed:2416192 ]
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. doi: 10.1016/0091-3057(86)90478-8. [PubMed:2426718 ]
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. doi: 10.1016/0165-1781(88)90016-9. [PubMed:2455302 ]
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 ]
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. doi: 10.1111/j.1471-4159.1984.tb02756.x. [PubMed:6198473 ]
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. doi: 10.1016/0378-4347(94)00464-g. [PubMed:7735466 ]
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. doi: 10.1016/0022-3956(96)00007-6. [PubMed:8884658 ]
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. doi: 10.1017/s1041610296002785. [PubMed:9116178 ]
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 ]
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 ]
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. doi: 10.1530/eje.0.1390493. [PubMed:9849813 ]
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. doi: 10.1016/s1566-0702(01)00385-x. [PubMed:11958479 ]
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. doi: 10.1212/01.wnl.0000144350.97844.94. [PubMed:15557528 ]
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. doi: 10.1017/S1461145705006231. Epub 2005 Nov 1. [PubMed:16259647 ]
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. doi: 10.1016/j.ymgme.2005.09.007. Epub 2005 Nov 9. [PubMed:16288991 ]

Showing metabocard for Homovanillyl alcohol (MMDBc0033654)

MOL for #<Metabolite:0x0000560bdd526f18>

3D MOL for #<Metabolite:0x0000560bdd526f18>

3D SDF for #<Metabolite:0x0000560bdd526f18>

3D-SDF for #<Metabolite:0x0000560bdd526f18>

PDB for #<Metabolite:0x0000560bdd526f18>

3D PDB for #<Metabolite:0x0000560bdd526f18>

SMILES for #<Metabolite:0x0000560bdd526f18>

INCHI for #<Metabolite:0x0000560bdd526f18>

Structure for #<Metabolite:0x0000560bdd526f18>

3D Structure for #<Metabolite:0x0000560bdd526f18>