NAV

N-{(2S)-3-[(1R)-1-aminoethyl](hydroxy)phosphoryl-2-benzylpropanoyl}-L-phenylalanine

Identification

Generic Name
N-{(2S)-3-[(1R)-1-aminoethyl](hydroxy)phosphoryl-2-benzylpropanoyl}-L-phenylalanine
DrugBank Accession Number
DB08506
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 418.4232
Monoisotopic: 418.165758496
Chemical Formula
C21H27N2O5P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAminopeptidase NNot AvailableEscherichia coli (strain K12)
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 phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine 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
Phenylalanine and derivatives
Alternative Parents
N-acyl-L-alpha-amino acids / Phenylpropanoic acids / Amphetamines and derivatives / Fatty amides / Secondary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organophosphorus compounds / Organic oxides
show 3 more
Substituents
3-phenylpropanoic-acid / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid / Fatty acyl / Fatty amide / Hydrocarbon derivative
show 15 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
MMWNOZXGYRPSCJ-LZQZEXGQSA-N
InChI
InChI=1S/C21H27N2O5P/c1-15(22)29(27,28)14-18(12-16-8-4-2-5-9-16)20(24)23-19(21(25)26)13-17-10-6-3-7-11-17/h2-11,15,18-19H,12-14,22H2,1H3,(H,23,24)(H,25,26)(H,27,28)/t15-,18-,19+/m1/s1
IUPAC Name
(2S)-2-[(2S)-3-{[(1R)-1-aminoethyl](hydroxy)phosphoryl}-2-benzylpropanamido]-3-phenylpropanoic acid
SMILES
[H][C@@](C)(N)[P@@](O)(=O)C[C@@]([H])(CC1=CC=CC=C1)C(=O)N[C@@]([H])(CC1=CC=CC=C1)C(O)=O

References

General References
Not Available
PubChem Compound
10601417
PubChem Substance
99444977
ChemSpider
8776790
ChEMBL
CHEMBL1235787
ZINC
ZINC000013807005
PDBe Ligand
S23
PDB Entries
2zxg

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 Solubility0.0362 mg/mLALOGPS
logP-0.13ALOGPS
logP0.66Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)-0.044Chemaxon
pKa (Strongest Basic)9.56Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area129.72 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity110.43 m3·mol-1Chemaxon
Polarizability41.88 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.837
Blood Brain Barrier+0.8465
Caco-2 permeable-0.7395
P-glycoprotein substrateSubstrate0.5083
P-glycoprotein inhibitor INon-inhibitor0.9692
P-glycoprotein inhibitor IINon-inhibitor1.0
Renal organic cation transporterNon-inhibitor0.9385
CYP450 2C9 substrateNon-substrate0.6702
CYP450 2D6 substrateNon-substrate0.8306
CYP450 3A4 substrateNon-substrate0.5898
CYP450 1A2 substrateNon-inhibitor0.9053
CYP450 2C9 inhibitorNon-inhibitor0.921
CYP450 2D6 inhibitorNon-inhibitor0.918
CYP450 2C19 inhibitorNon-inhibitor0.9334
CYP450 3A4 inhibitorNon-inhibitor0.7476
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9643
Ames testNon AMES toxic0.777
CarcinogenicityNon-carcinogens0.8596
BiodegradationNot ready biodegradable0.9282
Rat acute toxicity2.1110 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9975
hERG inhibition (predictor II)Non-inhibitor0.9292
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/MSsplash10-014i-0133900000-2475748148db260154eb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1002900000-8db45638122fa01191b8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9206100000-bcc225e376a044ad7e6b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gb9-0953300000-9cccb83892ff777628bc
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udj-3790000000-3d9ddb1da0addc74a4f4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kg-9701000000-0291f843feaf1ccef738
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]-189.66597
predicted
DeepCCS 1.0 (2019)
[M+H]+191.56148
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.39397
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Aminopeptidase N
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Aminopeptidase N is involved in the degradation of intracellular peptides generated by protein breakdown during normal growth as well as in response to nutrient starvation.
Gene Name
pepN
Uniprot ID
P04825
Uniprot Name
Aminopeptidase N
Molecular Weight
98917.975 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 21:32 / Updated at June 12, 2020 16:52