3-Fluorotyrosine

Identification

Name
3-Fluorotyrosine
Accession Number
DB04436  (EXPT03275)
Type
Small Molecule
Groups
Experimental
Description

3-fluorotyrosine is a solid. This compound belongs to the phenylpropanoic acids. These are compounds whose structure contain a benzene ring conjugated to a propanoic acid. 3-fluorotyrosine targets the protein superoxide dismutase [mn], mitochondrial.

Structure
Thumb
Synonyms
  • 3-fluoro-L-tyrosine
Categories
UNII
174NRG3M2X
CAS number
403-90-7
Weight
Average: 199.179
Monoisotopic: 199.064471396
Chemical Formula
C9H10FNO3
InChI Key
VIIAUOZUUGXERI-ZETCQYMHSA-N
InChI
InChI=1S/C9H10FNO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1
IUPAC Name
(2S)-2-amino-3-(3-fluoro-4-hydroxyphenyl)propanoic acid
SMILES
N[[email protected]@H](CC1=CC(F)=C(O)C=C1)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USuperoxide dismutase [Mn], mitochondrialNot AvailableHuman
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
Not Available
External Links
PubChem Compound
643330
PubChem Substance
46507213
ChemSpider
558483
ChEBI
46534
ChEMBL
CHEMBL1236909
HET
YOF
PDB Entries
1rrx / 1xdc / 1xil / 3fyg / 4qzs

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
melting point (°C)280 dec °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.19 mg/mLALOGPS
logP-2ALOGPS
logP-1.3ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.57ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.31 m3·mol-1ChemAxon
Polarizability18.31 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9828
Blood Brain Barrier-0.6699
Caco-2 permeable-0.5418
P-glycoprotein substrateNon-substrate0.6407
P-glycoprotein inhibitor INon-inhibitor0.9714
P-glycoprotein inhibitor IINon-inhibitor0.996
Renal organic cation transporterNon-inhibitor0.9226
CYP450 2C9 substrateNon-substrate0.8689
CYP450 2D6 substrateNon-substrate0.8561
CYP450 3A4 substrateNon-substrate0.7527
CYP450 1A2 substrateNon-inhibitor0.9465
CYP450 2C9 inhibitorNon-inhibitor0.9321
CYP450 2D6 inhibitorNon-inhibitor0.9318
CYP450 2C19 inhibitorNon-inhibitor0.9363
CYP450 3A4 inhibitorNon-inhibitor0.898
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9521
Ames testNon AMES toxic0.8189
CarcinogenicityNon-carcinogens0.894
BiodegradationNot ready biodegradable0.9307
Rat acute toxicity2.6177 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9751
hERG inhibition (predictor II)Non-inhibitor0.9244
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

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 / Amphetamines and derivatives / L-alpha-amino acids / O-fluorophenols / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / Fluorobenzenes / Aryl fluorides / Amino acids
show 8 more
Substituents
Tyrosine or derivatives / Phenylalanine or derivatives / 3-phenylpropanoic-acid / Alpha-amino acid / Amphetamine or derivatives / L-alpha-amino acid / 2-fluorophenol / 2-halophenol / 1-hydroxy-2-unsubstituted benzenoid / Halobenzene
show 24 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-tyrosine derivative, 3-fluorotyrosine (CHEBI:46534)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Superoxide dismutase activity
Specific Function
Destroys superoxide anion radicals which are normally produced within the cells and which are toxic to biological systems.
Gene Name
SOD2
Uniprot ID
P04179
Uniprot Name
Superoxide dismutase [Mn], mitochondrial
Molecular Weight
24721.955 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:27