Dihydroxyphenylalanine (CHEM003159)

Record Information
Version1.0
Creation Date2014-08-29 05:52:16 UTC
Update Date2026-03-27 00:47:50 UTC
Accession NumberCHEM003159
Identification
Common NameDihydroxyphenylalanine
ClassSmall Molecule
Description
Dihydroxyphenylalanine is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Dihydroxyphenylalanine(DOPA) is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline) collectively known as catecholamines. DOPA crosses the protective blood-brain barrier, whereas dopamine itself cannot. Thus, L-DOPA is used to increase dopamine concentrations in the treatment of Parkinson's disease and dopamine-responsive dystonia.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
Contaminant Type
  • Amine
  • Natural Compound
  • Organic Compound
  • Uremic Toxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-3-(3,4-Dihydroxyphenyl)alanineChEBI
(+-)-DopaChEBI
(R,S)-DopaChEBI
3',4'-DihydroxyphenylalanineChEBI
3-Hydroxy-DL-tyrosineChEBI
3-HydroxytyrosineChEBI
beta-(3,4-Dihydroxyphenyl)-DL-alpha-alanineChEBI
DL-3,4-DopaChEBI
DL-beta-(3,4-Dihydroxyphenyl)-alpha-alanineChEBI
DL-beta-(3,4-Dihydroxyphenyl)alanineChEBI
DL-DihydroxyphenylalanineChEBI
DL-DioxyphenylalanineChEBI
b-(3,4-Dihydroxyphenyl)-DL-a-alanineGenerator
Β-(3,4-dihydroxyphenyl)-DL-α-alanineGenerator
DL-b-(3,4-Dihydroxyphenyl)-a-alanineGenerator
DL-Β-(3,4-dihydroxyphenyl)-α-alanineGenerator
DL-b-(3,4-Dihydroxyphenyl)alanineGenerator
DL-Β-(3,4-dihydroxyphenyl)alanineGenerator
(+/-) 3-(3,4-dihydroxyphenyl)alanineHMDB
2-amino-3-(3,4-Dihydroxyphenyl)propanoateHMDB
2-amino-3-(3,4-Dihydroxyphenyl)propanoic acidHMDB
3,4-Dihydroxy-DL-phenylalanineHMDB
3,4-DihydroxyphenylalanineHMDB, MeSH
3-(3,4-Dihydroxyphenyl)-DL-alanineHMDB
a-amino-3,4-Dihydroxy-benzenepropanoateHMDB
a-amino-3,4-Dihydroxy-benzenepropanoic acidHMDB
alpha-amino-3,4-Dihydroxy-benzenepropanoateHMDB
alpha-amino-3,4-Dihydroxy-benzenepropanoic acidHMDB
alpha-amino-Hydrocaffeic acidHMDB
b-(3,4-Dihydroxyphenyl)-a-alanineHMDB
beta-(3,4-Dihydroxyphenyl)-alpha-alanineHMDB
DL-3',4'-DihydroxyphenylalanineHMDB
DL-3,4-DihydroxyphenylalanineHMDB
DL-3-HydroxytyrosineHMDB
DL-4,5-DihydroxyphenylalanineHMDB
DopaMeSH, HMDB
3 Hydroxy DL tyrosineMeSH, HMDB
3,4 DihydroxyphenylalanineMeSH, HMDB
beta-HydroxytyrosineMeSH, HMDB
Dihydroxyphenylalanine hydrochloride, (2:1)MeSH, HMDB
beta HydroxytyrosineMeSH, HMDB
DihydroxyphenylalanineMeSH, HMDB
Chemical FormulaC9H11NO4
Average Molecular Mass197.188 g/mol
Monoisotopic Mass197.069 g/mol
CAS Registry Number63-84-3
IUPAC Name2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
Traditional Name3',4'-dihydroxyphenylalanine
SMILESNC(CC1=CC=C(O)C(O)=C1)C(O)=O
InChI IdentifierInChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)
InChI KeyWTDRDQBEARUVNC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Alpha-amino acid
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.3 g/LALOGPS
logP-2.3ALOGPS
logP-1.8ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.65ChemAxon
pKa (Strongest Basic)9.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.78 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.08 m³·mol⁻¹ChemAxon
Polarizability19.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureEndogenous, Ingestion, Dermal (contact)
Mechanism of ToxicityUremic toxins such as dihydroxyphenylalanine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (2). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (3).
MetabolismUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNaturally produced by the body (endogenous).
Minimum Risk LevelNot Available
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
SymptomsAs a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.
TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0250744
FooDB IDFDB022140
Phenol Explorer IDNot Available
KNApSAcK IDC00018152
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDihydroxyphenylalanine
Chemspider ID813
ChEBI ID49168
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24117106