N-[(2R)-2-benzyl-4-(hydroxyamino)-4-oxobutanoyl]-L-alanine

Identification

Name
N-[(2R)-2-benzyl-4-(hydroxyamino)-4-oxobutanoyl]-L-alanine
Accession Number
DB08040
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
46BBW2U5D6
CAS number
Not Available
Weight
Average: 294.3031
Monoisotopic: 294.121571696
Chemical Formula
C14H18N2O5
InChI Key
OJCFZTVYDSKXNM-GXSJLCMTSA-N
InChI
InChI=1S/C14H18N2O5/c1-9(14(19)20)15-13(18)11(8-12(17)16-21)7-10-5-3-2-4-6-10/h2-6,9,11,21H,7-8H2,1H3,(H,15,18)(H,16,17)(H,19,20)/t9-,11+/m0/s1
IUPAC Name
(2S)-2-[(2R)-2-benzyl-3-(hydroxycarbamoyl)propanamido]propanoic acid
SMILES
[H][[email protected]@](C)(NC(=O)[[email protected]@]([H])(CC(=O)NO)CC1=CC=CC=C1)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ULeukotriene A-4 hydrolaseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
123982
PubChem Substance
99444511
ChemSpider
110501
BindingDB
92500
ChEMBL
CHEMBL85320
HET
KEL
PDB Entries
3b7u

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.433 mg/mLALOGPS
logP0.3ALOGPS
logP0.38ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.73 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity73.69 m3·mol-1ChemAxon
Polarizability29 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7634
Blood Brain Barrier+0.8595
Caco-2 permeable-0.7912
P-glycoprotein substrateNon-substrate0.6183
P-glycoprotein inhibitor INon-inhibitor0.9513
P-glycoprotein inhibitor IINon-inhibitor0.9967
Renal organic cation transporterNon-inhibitor0.9669
CYP450 2C9 substrateNon-substrate0.7792
CYP450 2D6 substrateNon-substrate0.8435
CYP450 3A4 substrateNon-substrate0.6277
CYP450 1A2 substrateNon-inhibitor0.9341
CYP450 2C9 inhibitorNon-inhibitor0.9562
CYP450 2D6 inhibitorNon-inhibitor0.9276
CYP450 2C19 inhibitorNon-inhibitor0.9357
CYP450 3A4 inhibitorNon-inhibitor0.9381
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9864
Ames testAMES toxic0.6996
CarcinogenicityNon-carcinogens0.8143
BiodegradationNot ready biodegradable0.7538
Rat acute toxicity1.9556 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9947
hERG inhibition (predictor II)Non-inhibitor0.9667
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-L-alpha-amino acids
Alternative Parents
Alanine and derivatives / N-acyl amines / Benzene and substituted derivatives / Secondary carboxylic acid amides / Hydroxamic acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
N-acyl-l-alpha-amino acid / Alanine or derivatives / Monocyclic benzene moiety / Fatty amide / Fatty acyl / Benzenoid / N-acyl-amine / Carboxamide group / Hydroxamic acid / Secondary carboxylic acid amide
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Leukotriene A-4 hydrolase
Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:27 / Updated on December 01, 2017 15:59