NAV

3-nitro-L-tyrosine

Identification

Generic Name
3-nitro-L-tyrosine
DrugBank Accession Number
DB03867
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 226.1861
Monoisotopic: 226.05897144
Chemical Formula
C9H10N2O5
Synonyms
  • (2S)-2-amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid
  • 3-Nitro-L-tyrosine
  • L-3-Nitrotyrosine
External IDs
  • NSC-37413
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGlutathione reductase, mitochondrialNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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 / Nitrophenols / Nitrobenzenes / Nitroaromatic compounds / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / Amino acids
show 10 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 3-phenylpropanoic-acid / Allyl-type 1,3-dipolar organic compound / Alpha-amino acid / Amine / Amino acid / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Benzenoid
show 26 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-tyrosine derivative, 3-nitrotyrosine (CHEBI:44454)
Affected organisms
Not Available

Chemical Identifiers

UNII
7COY1HA6HK
CAS number
621-44-3
InChI Key
FBTSQILOGYXGMD-LURJTMIESA-N
InChI
InChI=1S/C9H10N2O5/c10-6(9(13)14)3-5-1-2-8(12)7(4-5)11(15)16/h1-2,4,6,12H,3,10H2,(H,13,14)/t6-/m0/s1
IUPAC Name
(2S)-2-amino-3-(4-hydroxy-3-nitrophenyl)propanoic acid
SMILES
N[C@@H](CC1=CC(=C(O)C=C1)[N+]([O-])=O)C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0001904
PubChem Compound
65124
PubChem Substance
46507718
ChemSpider
58633
ChEBI
44454
ZINC
ZINC000034800261
PDBe Ligand
NIY
PDB Entries
1k4q / 1sda / 2adp / 2h5u / 2xak / 2xap / 2xav / 2xaw / 2xax / 2xay …
show 22 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.49 mg/mLALOGPS
logP-2.1ALOGPS
logP-1.5Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.1Chemaxon
pKa (Strongest Basic)9.46Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area126.69 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity53.42 m3·mol-1Chemaxon
Polarizability20.55 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6692
Blood Brain Barrier-0.7486
Caco-2 permeable-0.596
P-glycoprotein substrateNon-substrate0.6261
P-glycoprotein inhibitor INon-inhibitor0.9375
P-glycoprotein inhibitor IINon-inhibitor0.9875
Renal organic cation transporterNon-inhibitor0.9498
CYP450 2C9 substrateNon-substrate0.8382
CYP450 2D6 substrateNon-substrate0.8579
CYP450 3A4 substrateNon-substrate0.6359
CYP450 1A2 substrateNon-inhibitor0.851
CYP450 2C9 inhibitorNon-inhibitor0.7822
CYP450 2D6 inhibitorNon-inhibitor0.9335
CYP450 2C19 inhibitorNon-inhibitor0.8526
CYP450 3A4 inhibitorNon-inhibitor0.8606
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9678
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.7266
BiodegradationNot ready biodegradable0.6648
Rat acute toxicity2.1807 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8746
hERG inhibition (predictor II)Non-inhibitor0.9459
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
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-014i-2790000000-d2985346d8315d1d8794
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0zgi-5910000000-077a7552abc426243e20
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-2790000000-d2985346d8315d1d8794
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-001i-0940000000-67e8e69b7a6cdee33f61
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-05o9-3900000000-fb63e13d7517f3696858
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0kdu-9600000000-31b19bfbe0c1fd17697f
MS/MS Spectrum - , negativeLC-MS/MSsplash10-03di-0900000000-ee8213cb39c0e1019f31
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.0070998
predicted
DarkChem Lite v0.1.0
[M-H]-157.2179998
predicted
DarkChem Lite v0.1.0
[M-H]-145.6711
predicted
DeepCCS 1.0 (2019)
[M+H]+156.2507998
predicted
DarkChem Lite v0.1.0
[M+H]+155.8929998
predicted
DarkChem Lite v0.1.0
[M+H]+147.90779
predicted
DeepCCS 1.0 (2019)
[M+Na]+155.4531998
predicted
DarkChem Lite v0.1.0
[M+Na]+155.4229998
predicted
DarkChem Lite v0.1.0
[M+Na]+154.02745
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Glutathione reductase, mitochondrial
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Maintains high levels of reduced glutathione in the cytosol.
Gene Name
GSR
Uniprot ID
P00390
Uniprot Name
Glutathione reductase, mitochondrial
Molecular Weight
56256.565 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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52