METHYL 4-{[({[(2R,5S)-5-{[(2S)-2-(AMINOMETHYL)PYRROLIDIN-1-YL]CARBONYL}PYRROLIDIN-2-YL]METHYL}AMINO)CARBONYL]AMINO}BENZOATE

Identification

Name
METHYL 4-{[({[(2R,5S)-5-{[(2S)-2-(AMINOMETHYL)PYRROLIDIN-1-YL]CARBONYL}PYRROLIDIN-2-YL]METHYL}AMINO)CARBONYL]AMINO}BENZOATE
Accession Number
DB07328
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 403.4754
Monoisotopic: 403.221954441
Chemical Formula
C20H29N5O4
InChI Key
USDCNOQKDUFKRD-IKGGRYGDSA-N
InChI
InChI=1S/C20H29N5O4/c1-29-19(27)13-4-6-14(7-5-13)24-20(28)22-12-15-8-9-17(23-15)18(26)25-10-2-3-16(25)11-21/h4-7,15-17,23H,2-3,8-12,21H2,1H3,(H2,22,24,28)/t15-,16+,17+/m1/s1
IUPAC Name
methyl 4-[({[(2R,5S)-5-[(2S)-2-(aminomethyl)pyrrolidine-1-carbonyl]pyrrolidin-2-yl]methyl}carbamoyl)amino]benzoate
SMILES
[H][C@]1(CNC(=O)NC2=CC=C(C=C2)C(=O)OC)CC[C@]([H])(N1)C(=O)N1CCC[C@@]1([H])CN

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDipeptidyl peptidase 4Not 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
Toxicity
Not Available
Affected organisms
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

References

General References
Not Available
External Links
PubChem Compound
11840913
PubChem Substance
99443799
ChemSpider
10015418
ChEMBL
CHEMBL1230763
ZINC
ZINC000024803068
PDBe Ligand
AAF
PDB Entries
2g63

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 Solubility0.317 mg/mLALOGPS
logP0.24ALOGPS
logP0.2ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)12.79ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.79 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity109.06 m3·mol-1ChemAxon
Polarizability43.47 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6579
Blood Brain Barrier+0.5427
Caco-2 permeable-0.7339
P-glycoprotein substrateSubstrate0.747
P-glycoprotein inhibitor INon-inhibitor0.7953
P-glycoprotein inhibitor IINon-inhibitor0.9776
Renal organic cation transporterNon-inhibitor0.8612
CYP450 2C9 substrateNon-substrate0.7988
CYP450 2D6 substrateNon-substrate0.8093
CYP450 3A4 substrateNon-substrate0.6091
CYP450 1A2 substrateNon-inhibitor0.8338
CYP450 2C9 inhibitorNon-inhibitor0.824
CYP450 2D6 inhibitorNon-inhibitor0.9331
CYP450 2C19 inhibitorNon-inhibitor0.5973
CYP450 3A4 inhibitorNon-inhibitor0.8632
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.831
Ames testNon AMES toxic0.7332
CarcinogenicityNon-carcinogens0.9437
BiodegradationNot ready biodegradable0.6764
Rat acute toxicity2.2583 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.826
hERG inhibition (predictor II)Non-inhibitor0.6826
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/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 alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Benzoic acid esters / N-phenylureas / Pyrrolidinecarboxamides / Benzoyl derivatives / N-acylpyrrolidines / Tertiary carboxylic acid amides / Methyl esters / Ureas / Azacyclic compounds / Dialkylamines
show 6 more
Substituents
Alpha-amino acid amide / Amine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzoate ester / Benzoic acid or derivatives / Benzoyl / Carbonic acid derivative / Carbonyl group
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
N-acylpyrrolidine, benzoate ester (CHEBI:40440)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Virus receptor activity
Specific Function
Cell surface glycoprotein receptor involved in the costimulatory signal essential for T-cell receptor (TCR)-mediated T-cell activation. Acts as a positive regulator of T-cell coactivation, by bindi...
Gene Name
DPP4
Uniprot ID
P27487
Uniprot Name
Dipeptidyl peptidase 4
Molecular Weight
88277.935 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 15:20 / Updated on June 12, 2020 10:52

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