Identification

Name
D-Tyrosine
Accession Number
DB03839  (EXPT01295)
Type
Small Molecule
Groups
Experimental
Description

A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.

Structure
Thumb
Synonyms
  • (R)-2-Amino-3-(p-hydroxyphenyl)propionic acid
  • (R)-3-(p-Hydroxyphenyl)alanine
  • D-Tyr
  • D-Tyrosin
Categories
Not Available
UNII
Not Available
CAS number
556-02-5
Weight
Average: 181.1885
Monoisotopic: 181.073893223
Chemical Formula
C9H11NO3
InChI Key
OUYCCCASQSFEME-MRVPVSSYSA-N
InChI
InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1
IUPAC Name
(2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid
SMILES
N[[email protected]](CC1=CC=C(O)C=C1)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Soutourina O, Soutourina J, Blanquet S, Plateau P: Formation of D-tyrosyl-tRNATyr accounts for the toxicity of D-tyrosine toward Escherichia coli. J Biol Chem. 2004 Oct 8;279(41):42560-5. Epub 2004 Aug 2. [PubMed:15292242]
External Links
KEGG Compound
C06420
PubChem Compound
71098
PubChem Substance
46504669
ChemSpider
64252
ChEBI
58570
ChEMBL
CHEMBL1076637
HET
DTY
PDB Entries
1c4b / 1d7t / 1of6 / 1uno / 1xa0 / 1zea / 2h9e / 2igz / 2ih0 / 2la0
show 48 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility453 mg/L (at 25 °C)CRC HANDBOOK
Predicted Properties
PropertyValueSource
Water Solubility7.67 mg/mLALOGPS
logP-2.4ALOGPS
logP-1.5ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)9.19ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.1 m3·mol-1ChemAxon
Polarizability18.06 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9821
Blood Brain Barrier-0.876
Caco-2 permeable-0.618
P-glycoprotein substrateNon-substrate0.6478
P-glycoprotein inhibitor INon-inhibitor0.9925
P-glycoprotein inhibitor IINon-inhibitor0.9937
Renal organic cation transporterNon-inhibitor0.9126
CYP450 2C9 substrateNon-substrate0.8458
CYP450 2D6 substrateNon-substrate0.7971
CYP450 3A4 substrateNon-substrate0.7817
CYP450 1A2 substrateNon-inhibitor0.9649
CYP450 2C9 inhibitorNon-inhibitor0.9862
CYP450 2D6 inhibitorNon-inhibitor0.976
CYP450 2C19 inhibitorNon-inhibitor0.9324
CYP450 3A4 inhibitorNon-inhibitor0.9128
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9807
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9118
BiodegradationReady biodegradable0.763
Rat acute toxicity2.2474 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.969
hERG inhibition (predictor II)Non-inhibitor0.9692
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q0-0900000000-64b5df3e494e5df5c1be
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-c38735d64e2a16bd0c68
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-6900000000-6696908ff67c37922f99
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-941af648c85b3f0f7c66
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-1900000000-b7d3075f2496303aeb37
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-9700000000-c242deae91617b5e8735
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as tyrosine and derivatives. These 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
Phenylalanine and derivatives / Phenylpropanoic acids / D-alpha-amino acids / Amphetamines and derivatives / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds
show 4 more
Substituents
Tyrosine or derivatives / Phenylalanine or derivatives / 3-phenylpropanoic-acid / Alpha-amino acid / Amphetamine or derivatives / D-alpha-amino acid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine / Monocyclic benzene moiety
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
D-alpha-amino acid, tyrosine (CHEBI:28479) / Other amino acids (C06420)

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [PubMed:11278508]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:19