NAV

2-HYDROXY-5-{[(1E)-2-PHENYLETHYLIDENE]AMINO}-L-TYROSINE

Identification

Generic Name
2-HYDROXY-5-{[(1E)-2-PHENYLETHYLIDENE]AMINO}-L-TYROSINE
DrugBank Accession Number
DB06988
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 314.3358
Monoisotopic: 314.126657074
Chemical Formula
C17H18N2O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPhenylethylamine oxidaseNot AvailableArthrobacter globiformis
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
Not Available
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 / Resorcinols / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / Shiff bases / Amino acids / Propargyl-type 1,3-dipolar organic compounds
show 7 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 3-phenylpropanoic-acid / Aldimine / Alpha-amino acid / Amine / Amino acid / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Benzenoid
show 22 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
non-proteinogenic L-alpha-amino acid, L-tyrosine derivative, imine (CHEBI:39866)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
BSKROLLIUIDPDT-KUJOXMSCSA-N
InChI
InChI=1S/C17H18N2O4/c18-13(17(22)23)8-12-9-14(16(21)10-15(12)20)19-7-6-11-4-2-1-3-5-11/h1-5,7,9-10,13,20-21H,6,8,18H2,(H,22,23)/b19-7+/t13-/m0/s1
IUPAC Name
(2S)-2-amino-3-{2,4-dihydroxy-5-[(E)-(2-phenylethylidene)amino]phenyl}propanoic acid
SMILES
[H][C@](N)(CC1=CC(\N=C\CC2=CC=CC=C2)=C(O)C=C1O)C(O)=O

References

General References
Not Available
PubChem Compound
46937041
PubChem Substance
99443459
ChemSpider
25057256
ChEBI
39866
ZINC
ZINC000053683758
PDBe Ligand
2TY
PDB Entries
2cwv / 3amo / 3x40 / 3x41 / 5zpj / 5zpk / 5zpl / 5zpm

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 Solubility0.0792 mg/mLALOGPS
logP-0.27ALOGPS
logP-0.16Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)1.46Chemaxon
pKa (Strongest Basic)9.09Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area116.14 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity88.21 m3·mol-1Chemaxon
Polarizability32.53 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5132
Blood Brain Barrier-0.8451
Caco-2 permeable-0.7955
P-glycoprotein substrateNon-substrate0.5106
P-glycoprotein inhibitor INon-inhibitor0.9596
P-glycoprotein inhibitor IINon-inhibitor0.9511
Renal organic cation transporterNon-inhibitor0.8686
CYP450 2C9 substrateNon-substrate0.7531
CYP450 2D6 substrateNon-substrate0.8631
CYP450 3A4 substrateNon-substrate0.7046
CYP450 1A2 substrateNon-inhibitor0.6888
CYP450 2C9 inhibitorNon-inhibitor0.8937
CYP450 2D6 inhibitorNon-inhibitor0.8619
CYP450 2C19 inhibitorNon-inhibitor0.7937
CYP450 3A4 inhibitorNon-inhibitor0.7161
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8399
Ames testNon AMES toxic0.7623
CarcinogenicityNon-carcinogens0.8029
BiodegradationNot ready biodegradable0.9355
Rat acute toxicity2.0410 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9808
hERG inhibition (predictor II)Non-inhibitor0.9259
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 MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0h00-0492000000-cb578ea0525804548c55
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0192000000-493f912e32a02a0d0251
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fkl-2290000000-3a90566b53449496349a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uxr-1190000000-866765eabbb8f885481a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ufr-2930000000-6849b4ebb26fcc9a0d8b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0hkd-0920000000-3d4bc548739f596eab6e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-169.96535
predicted
DeepCCS 1.0 (2019)
[M+H]+172.32335
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.12546
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Phenylethylamine oxidase
Kind
Protein
Organism
Arthrobacter globiformis
Pharmacological action
Unknown
General Function
Tryptamine:oxygen oxidoreductase (deaminating) activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
P46881
Uniprot Name
Phenylethylamine oxidase
Molecular Weight
70645.405 Da
References
  1. 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. [Article]

Drug created at September 15, 2010 21:18 / Updated at June 12, 2020 16:52