(2S)-2-amino-5-oxo-5-[(4-phenylmethoxyphenyl)amino]pentanoic acid

Identification

Generic Name
(2S)-2-amino-5-oxo-5-[(4-phenylmethoxyphenyl)amino]pentanoic acid
DrugBank Accession Number
DB07102
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 328.3624
Monoisotopic: 328.142307138
Chemical Formula
C18H20N2O4
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ULeukotriene A-4 hydrolaseNot 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
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as glutamine and derivatives. These are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine 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
Glutamine and derivatives
Alternative Parents
L-alpha-amino acids / Anilides / Phenoxy compounds / Phenol ethers / N-arylamides / Alkyl aryl ethers / Fatty amides / Secondary carboxylic acid amides / Amino acids / Monocarboxylic acids and derivatives
show 6 more
Substituents
Alkyl aryl ether / Alpha-amino acid / Amine / Amino acid / Anilide / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid
show 20 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
BYSBXIPCDJNEBG-INIZCTEOSA-N
InChI
InChI=1S/C18H20N2O4/c19-16(18(22)23)10-11-17(21)20-14-6-8-15(9-7-14)24-12-13-4-2-1-3-5-13/h1-9,16H,10-12,19H2,(H,20,21)(H,22,23)/t16-/m0/s1
IUPAC Name
(2S)-2-amino-4-{[4-(benzyloxy)phenyl]carbamoyl}butanoic acid
SMILES
[H][C@](N)(CCC(=O)NC1=CC=C(OCC2=CC=CC=C2)C=C1)C(O)=O

References

General References
Not Available
PubChem Compound
24768560
PubChem Substance
99443573
ChemSpider
24699373
BindingDB
24256
ChEMBL
CHEMBL478381
ZINC
ZINC000024975367
PDBe Ligand
4BQ
PDB Entries
3chq

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 Solubility0.0094 mg/mLALOGPS
logP-0.31ALOGPS
logP-0.19Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)1.86Chemaxon
pKa (Strongest Basic)9.31Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area101.65 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity90.64 m3·mol-1Chemaxon
Polarizability34.76 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.735
Blood Brain Barrier+0.7743
Caco-2 permeable-0.8486
P-glycoprotein substrateNon-substrate0.5274
P-glycoprotein inhibitor INon-inhibitor0.9416
P-glycoprotein inhibitor IINon-inhibitor0.9411
Renal organic cation transporterNon-inhibitor0.884
CYP450 2C9 substrateNon-substrate0.8013
CYP450 2D6 substrateNon-substrate0.8532
CYP450 3A4 substrateNon-substrate0.5434
CYP450 1A2 substrateNon-inhibitor0.8187
CYP450 2C9 inhibitorNon-inhibitor0.7745
CYP450 2D6 inhibitorNon-inhibitor0.852
CYP450 2C19 inhibitorNon-inhibitor0.5803
CYP450 3A4 inhibitorNon-inhibitor0.8769
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8583
Ames testNon AMES toxic0.8237
CarcinogenicityNon-carcinogens0.9436
BiodegradationReady biodegradable0.6585
Rat acute toxicity1.9744 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9852
hERG inhibition (predictor II)Non-inhibitor0.8308
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-MSsplash10-0006-9441000000-7c6e28d171ac9009f1b4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-003r-3189000000-7bd7e702f815dbfbdbf0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-2269000000-1a013fe9623b8a6872bf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lu-5292000000-fe67f2c7d75a779895ae
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03ml-3932000000-f7ff6a852ce053a46c9a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-053u-9200000000-10db66ac4863bff85c98
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-02am-3900000000-2aa34fa374cfac31ff0b
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]-172.70709
predicted
DeepCCS 1.0 (2019)
[M+H]+175.06511
predicted
DeepCCS 1.0 (2019)
[M+Na]+181.91371
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Leukotriene A-4 hydrolase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Epoxide hydrolase that catalyzes the final step in the biosynthesis of the proinflammatory mediator leukotriene B4. Has also aminopeptidase activity.
Gene Name
LTA4H
Uniprot ID
P09960
Uniprot Name
Leukotriene A-4 hydrolase
Molecular Weight
69284.64 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