(2S)-2-amino-5-oxo-5-[(4-phenylmethoxyphenyl)amino]pentanoic acid
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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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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ALeukotriene A-4 hydrolase inhibitorHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- External Links
- PubChem Compound
- 24768560
- PubChem Substance
- 99443573
- ChemSpider
- 24699373
- BindingDB
- 24256
- ChEMBL
- CHEMBL478381
- ZINC
- ZINC000024975367
- PDBe Ligand
- 4BQ
- PDB Entries
- 3chq
Clinical Trials
- Clinical Trials
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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
Property Value Source Water Solubility 0.0094 mg/mL ALOGPS logP -0.31 ALOGPS logP -0.19 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 1.86 Chemaxon pKa (Strongest Basic) 9.31 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 101.65 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 90.64 m3·mol-1 Chemaxon Polarizability 34.76 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.735 Blood Brain Barrier + 0.7743 Caco-2 permeable - 0.8486 P-glycoprotein substrate Non-substrate 0.5274 P-glycoprotein inhibitor I Non-inhibitor 0.9416 P-glycoprotein inhibitor II Non-inhibitor 0.9411 Renal organic cation transporter Non-inhibitor 0.884 CYP450 2C9 substrate Non-substrate 0.8013 CYP450 2D6 substrate Non-substrate 0.8532 CYP450 3A4 substrate Non-substrate 0.5434 CYP450 1A2 substrate Non-inhibitor 0.8187 CYP450 2C9 inhibitor Non-inhibitor 0.7745 CYP450 2D6 inhibitor Non-inhibitor 0.852 CYP450 2C19 inhibitor Non-inhibitor 0.5803 CYP450 3A4 inhibitor Non-inhibitor 0.8769 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8583 Ames test Non AMES toxic 0.8237 Carcinogenicity Non-carcinogens 0.9436 Biodegradation Ready biodegradable 0.6585 Rat acute toxicity 1.9744 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9852 hERG inhibition (predictor II) Non-inhibitor 0.8308
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-9441000000-7c6e28d171ac9009f1b4 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-003r-3189000000-7bd7e702f815dbfbdbf0 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-2269000000-1a013fe9623b8a6872bf Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00lu-5292000000-fe67f2c7d75a779895ae Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03ml-3932000000-f7ff6a852ce053a46c9a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-053u-9200000000-10db66ac4863bff85c98 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-02am-3900000000-2aa34fa374cfac31ff0b Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 172.70709 predictedDeepCCS 1.0 (2019) [M+H]+ 175.06511 predictedDeepCCS 1.0 (2019) [M+Na]+ 181.91371 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsLeukotriene A-4 hydrolase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Bifunctional zinc metalloenzyme that comprises both epoxide hydrolase (EH) and aminopeptidase activities. Acts as an epoxide hydrolase to catalyze the conversion of LTA4 to the pro-inflammatory mediator leukotriene B4 (LTB4) (PubMed:11917124, PubMed:12207002, PubMed:15078870, PubMed:18804029, PubMed:1897988, PubMed:1975494, PubMed:2244921). Has also aminopeptidase activity, with high affinity for N-terminal arginines of various synthetic tripeptides (PubMed:18804029, PubMed:20813919). In addition to its pro-inflammatory EH activity, may also counteract inflammation by its aminopeptidase activity, which inactivates by cleavage another neutrophil attractant, the tripeptide Pro-Gly-Pro (PGP), a bioactive fragment of collagen generated by the action of matrix metalloproteinase-9 (MMP9) and prolylendopeptidase (PREPL) (PubMed:20813919, PubMed:24591641). Involved also in the biosynthesis of resolvin E1 and 18S-resolvin E1 from eicosapentaenoic acid, two lipid mediators that show potent anti-inflammatory and pro-resolving actions (PubMed:21206090)
- Specific Function
- aminopeptidase activity
- Gene Name
- LTA4H
- Uniprot ID
- P09960
- Uniprot Name
- Leukotriene A-4 hydrolase
- Molecular Weight
- 69284.64 Da
References
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at September 15, 2010 21:18 / Updated at August 26, 2024 19:22