NAV

D-phenylalanyl-N-benzyl-L-prolinamide

Identification

Generic Name
D-phenylalanyl-N-benzyl-L-prolinamide
DrugBank Accession Number
DB07143
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 351.4421
Monoisotopic: 351.194677059
Chemical Formula
C21H25N3O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProthrombinNot 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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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 / Pyrrolidinecarboxamides / N-acylpyrrolidines / Aralkylamines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Azacyclic compounds / Organopnictogen compounds
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Substituents
Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid or derivatives / Amphetamine or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid
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Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
MEPJWLFTTFHOQO-MOPGFXCFSA-N
InChI
InChI=1S/C21H25N3O2/c22-18(14-16-8-3-1-4-9-16)21(26)24-13-7-12-19(24)20(25)23-15-17-10-5-2-6-11-17/h1-6,8-11,18-19H,7,12-15,22H2,(H,23,25)/t18-,19+/m1/s1
IUPAC Name
(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]-N-benzylpyrrolidine-2-carboxamide
SMILES
[H][C@@](N)(CC1=CC=CC=C1)C(=O)N1CCC[C@@]1([H])C(=O)NCC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
25113125
PubChem Substance
99443614
ChemSpider
23200354
BindingDB
50133518
ChEMBL
CHEMBL116597
ZINC
ZINC000053165085
PDBe Ligand
53U
PDB Entries
2zff

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
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 Solubility0.0307 mg/mLALOGPS
logP1.59ALOGPS
logP1.95Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)14.55Chemaxon
pKa (Strongest Basic)7.7Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area75.43 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity101.43 m3·mol-1Chemaxon
Polarizability37.95 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9871
Blood Brain Barrier+0.8163
Caco-2 permeable-0.5201
P-glycoprotein substrateSubstrate0.6497
P-glycoprotein inhibitor INon-inhibitor0.526
P-glycoprotein inhibitor IINon-inhibitor0.5937
Renal organic cation transporterNon-inhibitor0.5403
CYP450 2C9 substrateNon-substrate0.8656
CYP450 2D6 substrateNon-substrate0.6366
CYP450 3A4 substrateNon-substrate0.648
CYP450 1A2 substrateNon-inhibitor0.8346
CYP450 2C9 inhibitorNon-inhibitor0.7631
CYP450 2D6 inhibitorNon-inhibitor0.7566
CYP450 2C19 inhibitorInhibitor0.7163
CYP450 3A4 inhibitorInhibitor0.7431
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.55
Ames testNon AMES toxic0.8787
CarcinogenicityNon-carcinogens0.8923
BiodegradationNot ready biodegradable0.9408
Rat acute toxicity2.2824 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9034
hERG inhibition (predictor II)Inhibitor0.6861
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-MSsplash10-0595-9540000000-6d10961ac4807d7436bd
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fdk-1894000000-e57e0ded6d2227b3d9d4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ufs-1923000000-66e666748204e6d9b34a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfu-5912000000-c76d97f85a875e7d6e1b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0v01-3790000000-bfa004d54a58f8777caf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-6900000000-3947f1110cec2a7d4d88
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zg3-6910000000-dcb6c40a2a83406c4fec
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]-179.80855
predicted
DeepCCS 1.0 (2019)
[M+H]+182.16655
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.10353
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Prothrombin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Thrombospondin receptor activity
Specific Function
Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostas...
Gene Name
F2
Uniprot ID
P00734
Uniprot Name
Prothrombin
Molecular Weight
70036.295 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 21:19 / Updated at June 12, 2020 16:52