ContaminantDB: Dihydroxyphenylalanine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:52:16 UTC

Update Date

2026-03-27 00:47:50 UTC

Accession Number

CHEM003159

Identification

Common Name

Dihydroxyphenylalanine

Class

Small 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-3-(3,4-Dihydroxyphenyl)alanine	ChEBI
(+-)-Dopa	ChEBI
(R,S)-Dopa	ChEBI
3',4'-Dihydroxyphenylalanine	ChEBI
3-Hydroxy-DL-tyrosine	ChEBI
3-Hydroxytyrosine	ChEBI
beta-(3,4-Dihydroxyphenyl)-DL-alpha-alanine	ChEBI
DL-3,4-Dopa	ChEBI
DL-beta-(3,4-Dihydroxyphenyl)-alpha-alanine	ChEBI
DL-beta-(3,4-Dihydroxyphenyl)alanine	ChEBI
DL-Dihydroxyphenylalanine	ChEBI
DL-Dioxyphenylalanine	ChEBI
b-(3,4-Dihydroxyphenyl)-DL-a-alanine	Generator
Β-(3,4-dihydroxyphenyl)-DL-α-alanine	Generator
DL-b-(3,4-Dihydroxyphenyl)-a-alanine	Generator
DL-Β-(3,4-dihydroxyphenyl)-α-alanine	Generator
DL-b-(3,4-Dihydroxyphenyl)alanine	Generator
DL-Β-(3,4-dihydroxyphenyl)alanine	Generator
(+/-) 3-(3,4-dihydroxyphenyl)alanine	HMDB
2-amino-3-(3,4-Dihydroxyphenyl)propanoate	HMDB
2-amino-3-(3,4-Dihydroxyphenyl)propanoic acid	HMDB
3,4-Dihydroxy-DL-phenylalanine	HMDB
3,4-Dihydroxyphenylalanine	HMDB, MeSH
3-(3,4-Dihydroxyphenyl)-DL-alanine	HMDB
a-amino-3,4-Dihydroxy-benzenepropanoate	HMDB
a-amino-3,4-Dihydroxy-benzenepropanoic acid	HMDB
alpha-amino-3,4-Dihydroxy-benzenepropanoate	HMDB
alpha-amino-3,4-Dihydroxy-benzenepropanoic acid	HMDB
alpha-amino-Hydrocaffeic acid	HMDB
b-(3,4-Dihydroxyphenyl)-a-alanine	HMDB
beta-(3,4-Dihydroxyphenyl)-alpha-alanine	HMDB
DL-3',4'-Dihydroxyphenylalanine	HMDB
DL-3,4-Dihydroxyphenylalanine	HMDB
DL-3-Hydroxytyrosine	HMDB
DL-4,5-Dihydroxyphenylalanine	HMDB
Dopa	MeSH, HMDB
3 Hydroxy DL tyrosine	MeSH, HMDB
3,4 Dihydroxyphenylalanine	MeSH, HMDB
beta-Hydroxytyrosine	MeSH, HMDB
Dihydroxyphenylalanine hydrochloride, (2:1)	MeSH, HMDB
beta Hydroxytyrosine	MeSH, HMDB
Dihydroxyphenylalanine	MeSH, HMDB

Chemical Formula

C₉H₁₁NO₄

Average Molecular Mass

197.188 g/mol

Monoisotopic Mass

197.069 g/mol

CAS Registry Number

63-84-3

IUPAC Name

2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

Traditional Name

3',4'-dihydroxyphenylalanine

SMILES

NC(CC1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=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 Key

WTDRDQBEARUVNC-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:49168 )
tyrosine derivative (CHEBI:49168 )
hydroxyphenylalanine (CHEBI:49168 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.3 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-1.8	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.65	ChemAxon
pKa (Strongest Basic)	9.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	103.78 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.08 m³·mol⁻¹	ChemAxon
Polarizability	19.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3900000000-e27bccc5fb602b6f1098	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0002-2391000000-1855886013a2095957cc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0ue9-0900000000-9a2dc91dda37ccd6d764	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a59-3900000000-51fb8377ac819b0b3100	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00or-9200000000-467c6d2d6b1c5185bac8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000b-0900000000-0805d147ed6a4a5615f5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-0900000000-0535cbfb1f2866998bd8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a59-0900000000-02a7e481355ecaedcf9f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-0900000000-664479c3e56237ecf94c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udr-0900000000-431d201400cf2fb08fad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-052r-0900000000-9177ea4b8f53bd44dc93	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-bf5afb57c3944eb31c73	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udr-0900000000-791d6239bfe8cf2cb189	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-0900000000-02a7e481355ecaedcf9f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-9de24eed142a3f0928f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000b-0900000000-412eb3979672d859993d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0900000000-2a1dc85195d73c3a878b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0900000000-02b57b8211288da98141	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-0f14fd981694b50996ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uea-0900000000-7cd68d059960262e024c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-31563ea2d36808cf260c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-8900000000-07fa521201594d25db7d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-079ea72e0cb84251b6c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0092-1900000000-6bcbd38a361ba2abf5bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9800000000-6e59379b40a21e5e2a33	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-65da392a07028d302f21	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k9i-0900000000-ec3a1ce52a52091b7d94	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-4900000000-51469f201a754d9d871d	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Endogenous, Ingestion, Dermal (contact)

Mechanism of Toxicity

Uremic 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).

Metabolism

Uremic 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 Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Naturally produced by the body (endogenous).

Minimum Risk Level

Not Available

Health Effects

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

Symptoms

As 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.

Treatment

Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0250744

FooDB ID

FDB022140

Phenol Explorer ID