Human Metabolome Database Version 3.5

Showing metabocard for Homovanillic acid (HMDB00118)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:54 -0700
HMDB ID HMDB00118
Secondary Accession Numbers
  • HMDB04285
Metabolite Identification
Common Name Homovanillic acid
Description Homovanillic acid is a dopamine metabolite occurring in human biofluids. A high proportion of patients with neuroblastoma excrete increased amounts of it in their urine. Homovanillic acid is a major catecholamine metabolite. It is used as a reagent to detect oxidative enzymes.(Wikipedia).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (4-Hydroxy-3-methoxyphenyl)acetate
  2. (4-Hydroxy-3-methoxyphenyl)acetic acid
  3. 3-Methoxy-4-hydroxy-phenylacetic acid
  4. 3-Methoxy-4-hydroxyphenylacetate
  5. 3-Methoxy-4-hydroxyphenylacetic acid
  6. 4-hydroxy 3-methoxyphenylacetic acid
  7. 4-Hydroxy-3-methoxybenzeneacetate
  8. 4-Hydroxy-3-methoxybenzeneacetic acid
  9. 4-Hydroxy-3-methoxyphenylacetic acid
  10. Homovanilate
  11. Homovanilic acid
  12. Homovanillate
  13. Homovanillinic acid
  14. Vanilacetate
  15. Vanilacetic acid
Chemical Formula C9H10O4
Average Molecular Weight 182.1733
Monoisotopic Molecular Weight 182.057908808
IUPAC Name 2-(4-hydroxy-3-methoxyphenyl)acetic acid
Traditional IUPAC Name homovanillic acid
CAS Registry Number 306-08-1
SMILES COC1=CC(CC(O)=O)=CC=C1O
InChI Identifier InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
InChI Key QRMZSPFSDQBLIX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Tyrosols and Derivatives
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • aromatic ether(ChEBI)
  • monocarboxylic acid(ChEBI)
Substituents
  • Alkyl Aryl Ether
  • Anisole
  • Carboxylic Acid
  • Methoxyphenol
  • Phenylacetate
Direct Parent Tyrosols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 138 - 140 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 17 mg/mL Not Available
LogP 0.33 LAHANN,TR ET AL. (1989)
Predicted Properties
Property Value Source
Water Solubility 2.72 g/L ALOGPS
LogP 1.02 ALOGPS
LogP 1.15 ChemAxon
LogS -1.83 ALOGPS
pKa (strongest acidic) 3.74 ChemAxon
pKa (strongest basic) -4.9 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.76 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 45.81 ChemAxon
Polarizability 17.74 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-MS
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Fibroblasts
  • Kidney
  • Brain
  • Striatum
  • Caudate Nucleus
  • Central Nervous System
  • Spinal Cord
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.082 +/- 0.050 uM Adult (>18 years old) Both Normal
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Blood Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Blood Detected and Quantified
0.048 +/- 0.009 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.03 +/- 0.006 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.047 +/- 0.01 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.078 +/- 0.029 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.029 +/- 0.045 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.027 +/- 0.004 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.029 +/- 0.005 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
0.166 +/- 0.147 uM Adult (>18 years old) Male Comment Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.574 (0.302-0.845) uM Infant (0-1 year old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.1521 +/- 0.0177 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.658-1.434 uM Children (1-13 year old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.324-1.098 uM Children (1-13 year old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.105-0.262 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.33-0.668 uM Children (1-13 year old) Male Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.346-0.716 uM Children (1-13 year old) Male Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.12 +/- 0.07 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
0.19+/- 0.093 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.28 (0.15-0.41) uM Adolescent (13-18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0004 +/- 0.00006 uM Adult (>18 years old) Male Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.89 +/- 0.47 uM Infant (0-1 year old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.78 +/- 0.42 uM Children (1-13 year old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.76 +/- 0.38 uM Children (1-13 year old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.71 +/- 0.34 uM Children (1-13 year old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.66 +/- 0.33 uM Infant (0-1 year old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.66 +/- 0.48 uM Children (1-13 year old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.54 +/- 0.211 uM Adolescent (13-18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.37 +/- 0.08 uM Adolescent (13-18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
1.14 +/- 0.54 uM Newborn (0-30 days old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.14 +/- 0.046 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.40 +/- 0.075 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.039 +/- 0.021 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.174 +/- 0.075 uM Adult (>18 years old) Male Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.202 +/- 0.094 uM Adult (>18 years old) Female Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.94 +/- 0.11 uM Children (1-13 year old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.384-0.765 uM Children (1-13 year old) Not Specified normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.401 +/- 0.188 uM Not Specified Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.20 (0.047-0.35) uM Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
2.26 +/- 1.58 umol/mmol creatinine Adult (>18 years old) Both Not Available
Urine Detected and Quantified
4.93 +/-3.37 umol/mmol creatinine Newborn (0-30 days old) Both Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
10.5 (2.0-19.0) umol/mmol creatinine Infant (0-1 year old) Not Specified Normal
Urine Detected and Quantified
17.1 (7.1-28.6) umol/mmol creatinine Newborn (0-30 days old) Both Normal
Urine Detected and Quantified
20.6 (15.6-31.0) umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected and Quantified
7.5 (3.6-14.6) umol/mmol creatinine Children (1-13 year old) Both Normal
Urine Detected and Quantified
5.6 (2.1-47.3) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
<=3.618 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
6.2 (1.8-12.7) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 574
  • Not Applicable
Urine Detected and Quantified
2.3 (0.9-5.5) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
2.2 (0.4-4.0) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
10.9 umol/mmol creatinine Infant (0-1 year old) Both Normal
Urine Detected and Quantified
0.0047 +/- 0.0027 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.133 +/- 0.015 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
4.3 (0.9-8.9) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.062 +/- 0.022 uM Adult (>18 years old) Male Schizophrenia
Blood Detected and Quantified 0.071 +/- 0.022 uM Adult (>18 years old) Female Schizophrenia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.39773 (0.155-0.654) uM Newborn (0-30 days old) Not Specified PNPO deficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 0.083 +/- 0.000 uM Infant (0-1 year old) Male Aromatic L-amino acid decarboxylase deficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 0.1347 +/- 0.0121 uM Adult (>18 years old) Not Specified Parkinsoni an syndrome
Cerebrospinal Fluid (CSF) Detected and Quantified 0.654 uM Newborn (0-30 days old) Not Specified PNPO deficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 0.155 uM Newborn (0-30 days old) Not Specified PNPO deficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 0.292 uM Newborn (0-30 days old) Not Specified PNPO deficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 0.49 uM Newborn (0-30 days old) Not Specified PNPO deficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 0.49 +/- 0.08 uM Children (1-13 year old) Both Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 0.39 +/- 0.091 uM Adult (>18 years old) Not Specified Narcolepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 0.21 +/- 0.08 uM Adult (>18 years old) Not Specified Growth hormone deficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 0.21 +/- 0.035 uM Adult (>18 years old) Female Schizophrenic disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.19 +/- 0.030 uM Adult (>18 years old) Female Schizophrenic disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.2572 +/- 0.1055 uM Adult (>18 years old) Not Specified Leuprolide acetate-induce hypogonadism
Cerebrospinal Fluid (CSF) Detected and Quantified 0.229 +/- 0.0782 uM Adult (>18 years old) Not Specified Leuprolide acetate-induced hypogonadism with testosterone replacment
Cerebrospinal Fluid (CSF) Detected and Quantified 0.21 +/- 0.12 uM Adult (>18 years old) Not Specified Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 0.05 +/- 0.03 uM Adult (>18 years old) Not Specified Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 0.05 +/- 0.04 uM Adult (>18 years old) Both Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 0.19 +/- 0.09 uM Adult (>18 years old) Not Specified Epilepsy
Cerebrospinal Fluid (CSF) Detected and Quantified 0.20 +/- 0.09 uM Adult (>18 years old) Both Comment Major depression
Cerebrospinal Fluid (CSF) Detected and Quantified 0.17 +/- 0.084 uM Adult (>18 years old) Not Specified Panic Disorder
Cerebrospinal Fluid (CSF) Detected and Quantified 0.16 +/- 0.095 uM Elderly (>65 years old) Not Specified Parkinson's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.17 +/- 0.01 uM Adult (>18 years old) Not Specified Olivopontocerebellar atrophy (OPCA)
Cerebrospinal Fluid (CSF) Detected and Quantified 0.17 +/- 0.01 uM Not Specified Not Specified Friedreich's ataxia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.15 +/- 0.03 uM Adult (>18 years old) Not Specified Spastic Ataxia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.50 +/- 0.32 uM Children (1-13 year old) Not Specified Autism
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0002 +/- 0.00005 uM Adult (>18 years old) Both Hypothyroidism
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00137 (0.000604-0.00225) uM Adult (>18 years old) Both Schizophrenia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.038 +/- 0.016 uM Adult (>18 years old) Both Schizophrenia
Cerebrospinal Fluid (CSF) Detected and Quantified 0.00017 (0.00013-0.00022) uM Adult (>18 years old) Both Hypothyroidism
Cerebrospinal Fluid (CSF) Detected and Quantified 0.1282 +/- 0.0583 uM Not Specified Both celiac disease
Cerebrospinal Fluid (CSF) Detected and Quantified 0.0585 (0.055-0.062) uM Children (1-13 year old) Not Specified sepiapterin reductase deficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 0.187 +/- 0.065 uM Adult (>18 years old) Not Specified Parkinson disease
Urine Detected and Quantified 2.9 +/- 0.0 umol/mmol creatinine Infant (0-1 year old) Male Aromatic L-amino acid decarboxylase deficiency
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Comment Hypertension (mild)
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Comment Hypertension (mild)
Associated Disorders and Diseases
Disease References
Hypothyroidism
  • 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 Link_out
      Narcolepsy
      • Strittmatter M, Isenberg E, Grauer MT, Hamann G, Schimrigk K: CSF substance P somatostatin and monoaminergic transmitter metabolites in patients with narcolepsy. Neurosci Lett. 1996 Nov 1;218(2):99-102. Pubmed: 8945737 Link_out
          Growth hormone deficiency
          • Burman P, Hetta J, Wide L, Mansson JE, Ekman R, Karlsson FA: Growth hormone treatment affects brain neurotransmitters and thyroxine [see comment] Clin Endocrinol (Oxf). 1996 Mar;44(3):319-24. Pubmed: 8729530 Link_out
              Schizophrenia
              • 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 Link_out
              • Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. Pubmed: 7595563 Link_out
              • 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 Link_out
                  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 Link_out
                  • Shaywitz BA, Cohen DJ, Bowers MB: Reduced cerebrospinal fluid 5-hydroxyindoleacetic acid and homovanillic acid in children with epilepsy. Neurology. 1975 Jan;25(1):72-9. Pubmed: 803305 Link_out
                      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 Link_out
                          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 Link_out
                              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 Link_out
                                  Autism
                                  • Narayan M, Srinath S, Anderson GM, Meundi DB: Cerebrospinal fluid levels of homovanillic acid and 5-hydroxyindoleacetic acid in autism. Biol Psychiatry. 1993 Apr 15-May 1;33(8-9):630-5. Pubmed: 7687150 Link_out
                                      Parkinson's disease
                                      • LeWitt PA, Galloway MP, Matson W, Milbury P, McDermott M, Srivastava DK, Oakes D: Markers of dopamine metabolism in Parkinson's disease. The Parkinson Study Group. Neurology. 1992 Nov;42(11):2111-7. Pubmed: 1436520 Link_out
                                          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 Link_out
                                              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 Link_out
                                                  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 Link_out
                                                      Associated OMIM IDs
                                                      DrugBank ID Not Available
                                                      DrugBank Metabolite ID Not Available
                                                      Phenol Explorer Compound ID 574 Link_out
                                                      Phenol Explorer Metabolite ID 574 Link_out
                                                      FoodDB ID FDB001783
                                                      KNApSAcK ID C00029504 Link_out
                                                      Chemspider ID 1675 Link_out
                                                      KEGG Compound ID C05582 Link_out
                                                      BioCyc ID Not Available
                                                      BiGG ID 46066 Link_out
                                                      Wikipedia Link Homovanillic acid Link_out
                                                      NuGOwiki Link HMDB00118 Link_out
                                                      Metagene Link HMDB00118 Link_out
                                                      METLIN ID 971 Link_out
                                                      PubChem Compound 1738 Link_out
                                                      PDB ID Not Available
                                                      ChEBI ID 545959 Link_out
                                                      References
                                                      Synthesis Reference Not Available
                                                      Material Safety Data Sheet (MSDS) Download (PDF)
                                                      General References
                                                      1. Needlman R, Zuckerman B, Anderson GM, Mirochnick M, Cohen DJ: Cerebrospinal fluid monoamine precursors and metabolites in human neonates following in utero cocaine exposure: a preliminary study. Pediatrics. 1993 Jul;92(1):55-60. Pubmed: 8516085 Link_out
                                                      2. Houston JP, Maas JW, Bowden CL, Contreras SA, McIntyre KL, Javors MA: Cerebrospinal fluid HVA, central brain atrophy, and clinical state in schizophrenia. Psychiatry Res. 1986 Nov;19(3):207-14. Pubmed: 3797547 Link_out
                                                      3. Scatton B, Dennis T, L'Heureux R, Monfort JC, Duyckaerts C, Javoy-Agid F: Degeneration of noradrenergic and serotonergic but not dopaminergic neurones in the lumbar spinal cord of parkinsonian patients. Brain Res. 1986 Aug 13;380(1):181-5. Pubmed: 2428421 Link_out
                                                      4. 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 Link_out
                                                      5. Court JA, Lloyd S, Thomas N, Piggott MA, Marshall EF, Morris CM, Lamb H, Perry RH, Johnson M, Perry EK: Dopamine and nicotinic receptor binding and the levels of dopamine and homovanillic acid in human brain related to tobacco use. Neuroscience. 1998 Nov;87(1):63-78. Pubmed: 9722142 Link_out
                                                      6. Reynolds GP, Garrett NJ: Striatal dopamine and homovanillic acid in Huntington's disease. J Neural Transm. 1986;65(2):151-5. Pubmed: 2939198 Link_out
                                                      7. Kay AD, Schapiro MB, Riker AK, Haxby JV, Rapoport SI, Cutler NR: Cerebrospinal fluid monoaminergic metabolites are elevated in adults with Down's syndrome. Ann Neurol. 1987 Apr;21(4):408-11. Pubmed: 2437853 Link_out
                                                      8. Lovenberg W, Levine RA, Robinson DS, Ebert M, Williams AC, Calne DB: Hydroxylase cofactor activity in cerebrospinal fluid of normal subjects and patients with Parkinson's disease. Science. 1979 May 11;204(4393):624-6. Pubmed: 432666 Link_out
                                                      9. Ruberg M, Javoy-Agid F, Hirsch E, Scatton B, LHeureux R, Hauw JJ, Duyckaerts C, Gray F, Morel-Maroger A, Rascol A, et al.: Dopaminergic and cholinergic lesions in progressive supranuclear palsy. Ann Neurol. 1985 Nov;18(5):523-9. Pubmed: 3000280 Link_out
                                                      10. Kaminski R, Powchick P, Warne PA, Goldstein M, McQueeney RT, Davidson M: Measurement of plasma homovanillic acid concentrations in schizophrenic patients. Prog Neuropsychopharmacol Biol Psychiatry. 1990;14(3):271-87. Pubmed: 2193315 Link_out
                                                      11. Birkmayer W, Birkmayer GJ: Nicotinamidadenindinucleotide (NADH): the new approach in the therapy of Parkinson's disease. Ann Clin Lab Sci. 1989 Jan-Feb;19(1):38-43. Pubmed: 2644889 Link_out
                                                      12. Lambert GW, Eisenhofer G, Jennings GL, Esler MD: Regional homovanillic acid production in humans. Life Sci. 1993;53(1):63-75. Pubmed: 8515683 Link_out
                                                      13. Pifl C, Schingnitz G, Hornykiewicz O: The neurotoxin MPTP does not reproduce in the rhesus monkey the interregional pattern of striatal dopamine loss typical of human idiopathic Parkinson's disease. Neurosci Lett. 1988 Oct 5;92(2):228-33. Pubmed: 3263594 Link_out
                                                      14. Grant DB, Dunger DB, Smith I, Hyland K: Familial glucocorticoid deficiency with achalasia of the cardia associated with mixed neuropathy, long-tract degeneration and mild dementia. Eur J Pediatr. 1992 Feb;151(2):85-9. Pubmed: 1537368 Link_out
                                                      15. 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 Link_out
                                                      16. Lepore V, Di Reda N, Defazio G, Pedone D, Giovine A, Lanzi C, Tartaglione B, Livrea P: Dopaminomimetic action of diphenylhydantoin in rat striatum: effect on homovanillic acid and cyclic AMP levels. Psychopharmacology (Berl). 1985;86(1-2):27-30. Pubmed: 2991966 Link_out
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                                                      Enzymes
                                                      Name: Catechol O-methyltransferase
                                                      Reactions:
                                                      S-Adenosylmethionine + 3,4-Dihydroxybenzeneacetic acid unknown S-Adenosylhomocysteine + Homovanillic acid details
                                                      Gene Name: COMT
                                                      Uniprot ID: P21964 Link_out
                                                      Protein Sequence: FASTA
                                                      Gene Sequence: FASTA
                                                      Name: Aldehyde dehydrogenase, dimeric NADP-preferring
                                                      Reactions:
                                                      Homovanillin + NAD + Water unknown Homovanillic acid + NADH + Hydrogen Ion details
                                                      Homovanillin + NADP + Water unknown Homovanillic acid + NADPH + Hydrogen Ion details
                                                      Gene Name: ALDH3A1
                                                      Uniprot ID: P30838 Link_out
                                                      Protein Sequence: FASTA
                                                      Gene Sequence: FASTA
                                                      Name: Aldehyde dehydrogenase family 1 member A3
                                                      Reactions:
                                                      Homovanillin + NAD + Water unknown Homovanillic acid + NADH + Hydrogen Ion details
                                                      Homovanillin + NADP + Water unknown Homovanillic acid + NADPH + Hydrogen Ion details
                                                      Gene Name: ALDH1A3
                                                      Uniprot ID: P47895 Link_out
                                                      Protein Sequence: FASTA
                                                      Gene Sequence: FASTA
                                                      Name: Aldehyde dehydrogenase family 3 member B2
                                                      Reactions:
                                                      Homovanillin + NAD + Water unknown Homovanillic acid + NADH + Hydrogen Ion details
                                                      Homovanillin + NADP + Water unknown Homovanillic acid + NADPH + Hydrogen Ion details
                                                      Gene Name: ALDH3B2
                                                      Uniprot ID: P48448 Link_out
                                                      Protein Sequence: FASTA
                                                      Gene Sequence: FASTA
                                                      Name: Aldehyde dehydrogenase family 3 member B1
                                                      Reactions:
                                                      Homovanillin + NAD + Water unknown Homovanillic acid + NADH + Hydrogen Ion details
                                                      Homovanillin + NADP + Water unknown Homovanillic acid + NADPH + Hydrogen Ion details
                                                      Gene Name: ALDH3B1
                                                      Uniprot ID: P43353 Link_out
                                                      Protein Sequence: FASTA
                                                      Gene Sequence: FASTA