NAV

N-BENZYLOXYCARBONYL-ALA-PRO-3-AMINO-4-PHENYL-BUTAN-2-OL

Identification

Generic Name
N-BENZYLOXYCARBONYL-ALA-PRO-3-AMINO-4-PHENYL-BUTAN-2-OL
DrugBank Accession Number
DB06886
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 467.5573
Monoisotopic: 467.242021181
Chemical Formula
C26H33N3O5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USubtilisin DYNot AvailableBacillus licheniformis
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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Proline and derivatives / Alpha amino acid amides / Amphetamines and derivatives / Benzyloxycarbonyls / Pyrrolidinecarboxamides / N-acylpyrrolidines / Tertiary carboxylic acid amides / Carbamate esters / Organic carbonic acids and derivatives / Secondary carboxylic acid amides
show 7 more
Substituents
Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amphetamine or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzyloxycarbonyl / Carbamic acid ester
show 20 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
MACLRJNEKXUAJK-YDLSIGKMSA-N
InChI
InChI=1S/C26H33N3O5/c1-18(27-26(33)34-17-21-12-7-4-8-13-21)25(32)29-15-9-14-23(29)24(31)28-22(19(2)30)16-20-10-5-3-6-11-20/h3-8,10-13,18-19,22-23,30H,9,14-17H2,1-2H3,(H,27,33)(H,28,31)/t18-,19+,22-,23-/m0/s1
IUPAC Name
benzyl N-[(2S)-1-[(2S)-2-{[(2S,3R)-3-hydroxy-1-phenylbutan-2-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamate
SMILES
[H][C@](C)(O)[C@]([H])(CC1=CC=CC=C1)NC(=O)[C@]1([H])CCCN1C(=O)[C@]([H])(C)NC(=O)OCC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
6323185
PubChem Substance
99443357
ChemSpider
4883307
ZINC
ZINC000015289930
PDBe Ligand
1BH
PDB Entries
1bh6

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 Solubility0.0149 mg/mLALOGPS
logP1.87ALOGPS
logP2.54Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)13.29Chemaxon
pKa (Strongest Basic)-2.8Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area107.97 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity127.63 m3·mol-1Chemaxon
Polarizability50.61 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.7496
Blood Brain Barrier-0.9005
Caco-2 permeable-0.8249
P-glycoprotein substrateSubstrate0.8541
P-glycoprotein inhibitor IInhibitor0.5757
P-glycoprotein inhibitor IIInhibitor0.7271
Renal organic cation transporterNon-inhibitor0.7898
CYP450 2C9 substrateNon-substrate0.7866
CYP450 2D6 substrateNon-substrate0.8339
CYP450 3A4 substrateSubstrate0.5493
CYP450 1A2 substrateNon-inhibitor0.7654
CYP450 2C9 inhibitorNon-inhibitor0.8017
CYP450 2D6 inhibitorNon-inhibitor0.8086
CYP450 2C19 inhibitorNon-inhibitor0.5
CYP450 3A4 inhibitorInhibitor0.8405
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5475
Ames testNon AMES toxic0.8806
CarcinogenicityNon-carcinogens0.9224
BiodegradationNot ready biodegradable0.9231
Rat acute toxicity2.4167 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9386
hERG inhibition (predictor II)Inhibitor0.5654
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/MSsplash10-0gdi-2679400000-d65a583f32fcf770668e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-2239100000-e9a701d1ff88e0748a73
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-7932100000-8a3f8506933e97af1ca1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-8659000000-5bfdb58b9ee25e44c741
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-7920100000-1941d7dedd6a65edde78
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-8962000000-9100be1d97d132ab01f6
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]-205.66743
predicted
DeepCCS 1.0 (2019)
[M+H]+207.56284
predicted
DeepCCS 1.0 (2019)
[M+Na]+213.34085
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Subtilisin DY
Kind
Protein
Organism
Bacillus licheniformis
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Subtilisin is an extracellular alkaline serine protease, it catalyzes the hydrolysis of proteins and peptide amides.
Gene Name
apr
Uniprot ID
P00781
Uniprot Name
Subtilisin DY
Molecular Weight
27435.335 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 21:17 / Updated at June 12, 2020 16:52