2-Hydroxy-5-({1-[(2-Naphthyloxy)Methyl]-3-Oxoprop-1-Enyl}Amino)Tyrosine

Identification

Generic Name
2-Hydroxy-5-({1-[(2-Naphthyloxy)Methyl]-3-Oxoprop-1-Enyl}Amino)Tyrosine
DrugBank Accession Number
DB02511
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 422.4306
Monoisotopic: 422.147786446
Chemical Formula
C23H22N2O6
Synonyms
  • 2-Hydroxy-5-{[(2E)-1-(2-naphthyloxy)-4-oxo-2-buten-2-yl]amino}-L-tyrosine

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 / Naphthalenes / p-Aminophenols / o-Aminophenols / Aniline and substituted anilines / Resorcinols / 1-hydroxy-2-unsubstituted benzenoids
show 14 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 3-phenylpropanoic-acid / Aldehyde / Alkyl aryl ether / Alpha,beta-unsaturated aldehyde / Alpha-amino acid / Amine / Amino acid / Aminophenol / Amphetamine or derivatives
show 31 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
PZWMZAFFUAWVDN-CQXYXCHQSA-N
InChI
InChI=1S/C23H22N2O6/c24-19(23(29)30)10-16-11-20(22(28)12-21(16)27)25-17(7-8-26)13-31-18-6-5-14-3-1-2-4-15(14)9-18/h1-9,11-12,19,25,27-28H,10,13,24H2,(H,29,30)/b17-7+/t19-/m0/s1
IUPAC Name
(2S)-2-amino-3-(2,4-dihydroxy-5-{[(2E)-1-(naphthalen-2-yloxy)-4-oxobut-2-en-2-yl]amino}phenyl)propanoic acid
SMILES
[H][C@](N)(CC1=C(O)C=C(O)C(N\C(COC2=CC=C3C=CC=CC3=C2)=C\C=O)=C1)C(O)=O

References

General References
Not Available
PubChem Compound
17754104
PubChem Substance
46507750
ChemSpider
26329750
ZINC
ZINC000012502206
PDBe Ligand
NBQ
PDB Entries
1sii

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 Solubility0.00714 mg/mLALOGPS
logP0.7ALOGPS
logP-0.2Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)1.69Chemaxon
pKa (Strongest Basic)8.98Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area142.11 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity117.43 m3·mol-1Chemaxon
Polarizability43.81 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5936
Blood Brain Barrier-0.9664
Caco-2 permeable-0.7621
P-glycoprotein substrateSubstrate0.6912
P-glycoprotein inhibitor INon-inhibitor0.8553
P-glycoprotein inhibitor IINon-inhibitor0.9126
Renal organic cation transporterNon-inhibitor0.9071
CYP450 2C9 substrateNon-substrate0.7581
CYP450 2D6 substrateNon-substrate0.8589
CYP450 3A4 substrateNon-substrate0.6068
CYP450 1A2 substrateInhibitor0.6422
CYP450 2C9 inhibitorNon-inhibitor0.7558
CYP450 2D6 inhibitorNon-inhibitor0.7995
CYP450 2C19 inhibitorNon-inhibitor0.6102
CYP450 3A4 inhibitorNon-inhibitor0.8049
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6534
Ames testAMES toxic0.5441
CarcinogenicityNon-carcinogens0.9236
BiodegradationNot ready biodegradable0.8216
Rat acute toxicity2.2396 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9383
hERG inhibition (predictor II)Non-inhibitor0.7747
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, Positive (Annotated)Predicted LC-MS/MSsplash10-05di-0039600000-eecff9a7bef10c38967a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0036-0390000000-ff16fdd3c1274cefa187
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01u0-0049100000-828dfd3b9418632984fd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-070f-1449000000-3eb12acd25dd39156f16
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0900000000-1738d3a072213523f663
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0931000000-744c1810057c6b77c887
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]-195.1394
predicted
DeepCCS 1.0 (2019)
[M+H]+197.51823
predicted
DeepCCS 1.0 (2019)
[M+Na]+203.59056
predicted
DeepCCS 1.0 (2019)

Targets

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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. 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]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 14, 2023 19:13