NAV

D-phenylalanyl-N-(3-methylbenzyl)-L-prolinamide

Identification

Generic Name
D-phenylalanyl-N-(3-methylbenzyl)-L-prolinamide
DrugBank Accession Number
DB07133
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 365.4687
Monoisotopic: 365.210327123
Chemical Formula
C22H27N3O2
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
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
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 / Pyrrolidinecarboxamides / N-acylpyrrolidines / Toluenes / Aralkylamines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Azacyclic 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
CHKWABXWPATIIG-UXHICEINSA-N
InChI
InChI=1S/C22H27N3O2/c1-16-7-5-10-18(13-16)15-24-21(26)20-11-6-12-25(20)22(27)19(23)14-17-8-3-2-4-9-17/h2-5,7-10,13,19-20H,6,11-12,14-15,23H2,1H3,(H,24,26)/t19-,20+/m1/s1
IUPAC Name
(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]-N-[(3-methylphenyl)methyl]pyrrolidine-2-carboxamide
SMILES
[H][C@@](N)(CC1=CC=CC=C1)C(=O)N1CCC[C@@]1([H])C(=O)NCC1=CC(C)=CC=C1

References

General References
Not Available
PubChem Compound
25021183
PubChem Substance
99443604
ChemSpider
25060226
ZINC
ZINC000039024292
PDBe Ligand
51U
PDB Entries
2zf0

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 Solubility0.0119 mg/mLALOGPS
logP1.69ALOGPS
logP2.47Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.6Chemaxon
pKa (Strongest Basic)7.7Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area75.43 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity106.48 m3·mol-1Chemaxon
Polarizability40.18 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9894
Blood Brain Barrier+0.7018
Caco-2 permeable-0.5164
P-glycoprotein substrateSubstrate0.7278
P-glycoprotein inhibitor IInhibitor0.5
P-glycoprotein inhibitor IINon-inhibitor0.5204
Renal organic cation transporterNon-inhibitor0.5633
CYP450 2C9 substrateNon-substrate0.8277
CYP450 2D6 substrateNon-substrate0.6475
CYP450 3A4 substrateNon-substrate0.5842
CYP450 1A2 substrateNon-inhibitor0.8671
CYP450 2C9 inhibitorNon-inhibitor0.7378
CYP450 2D6 inhibitorNon-inhibitor0.7259
CYP450 2C19 inhibitorInhibitor0.7246
CYP450 3A4 inhibitorInhibitor0.7742
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5136
Ames testNon AMES toxic0.9012
CarcinogenicityNon-carcinogens0.875
BiodegradationNot ready biodegradable0.9683
Rat acute toxicity2.2747 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8953
hERG inhibition (predictor II)Inhibitor0.7377
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-MSsplash10-006w-9750000000-20f3c9a228bae8462e6a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-1694000000-19e21197f04bbe9b8d84
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01vk-1976000000-98f8bd802027fe878e6b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aor-2912000000-6c7b20db71cf3e63e4a6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00r2-2891000000-c5a3cf63d6a29fba8007
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0abc-6910000000-0bd7075e6f68876fa13e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0lmm-5910000000-bade5a379b601cba2cb2
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]-185.04515
predicted
DeepCCS 1.0 (2019)
[M+H]+187.4407
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.47235
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