1-{[1-(2-AMINO-3-PHENYL-PROPIONYL)-PYRROLIDINE-2-CARBONYL]-AMINO}-2-(3-CYANO-PHENYL)-ETHANEBORONIC ACID

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
1-{[1-(2-AMINO-3-PHENYL-PROPIONYL)-PYRROLIDINE-2-CARBONYL]-AMINO}-2-(3-CYANO-PHENYL)-ETHANEBORONIC ACID
Accession Number
DB08420
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: 434.296
Monoisotopic: 434.212535838
Chemical Formula
C23H27BN4O4
InChI Key
UFOIPTZMXQILSG-HKBOAZHASA-N
InChI
InChI=1S/C23H27BN4O4/c25-15-18-9-4-8-17(12-18)14-21(24(31)32)27-22(29)20-10-5-11-28(20)23(30)19(26)13-16-6-2-1-3-7-16/h1-4,6-9,12,19-21,31-32H,5,10-11,13-14,26H2,(H,27,29)/t19-,20+,21+/m1/s1
IUPAC Name
[(1R)-1-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-2-(3-cyanophenyl)ethyl]boronic acid
SMILES
[H][C@@](N)(CC1=CC=CC=C1)C(=O)N1CCC[C@@]1([H])C(=O)N[C@@]([H])(CC1=CC(=CC=C1)C#N)B(O)O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTrypsin-1Not 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
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5289192
PubChem Substance
99444891
ChemSpider
4451206
HET
PPB
PDB Entries
1auj

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 Solubility0.0391 mg/mLALOGPS
logP1.26ALOGPS
logP2.19ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)12.55ChemAxon
pKa (Strongest Basic)7.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area139.68 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity115.6 m3·mol-1ChemAxon
Polarizability45.92 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7826
Blood Brain Barrier-0.6254
Caco-2 permeable-0.6838
P-glycoprotein substrateSubstrate0.6616
P-glycoprotein inhibitor INon-inhibitor0.8162
P-glycoprotein inhibitor IINon-inhibitor0.9449
Renal organic cation transporterNon-inhibitor0.7905
CYP450 2C9 substrateNon-substrate0.7734
CYP450 2D6 substrateNon-substrate0.777
CYP450 3A4 substrateNon-substrate0.5943
CYP450 1A2 substrateNon-inhibitor0.9077
CYP450 2C9 inhibitorNon-inhibitor0.7735
CYP450 2D6 inhibitorNon-inhibitor0.918
CYP450 2C19 inhibitorNon-inhibitor0.7322
CYP450 3A4 inhibitorNon-inhibitor0.5152
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9512
Ames testNon AMES toxic0.7006
CarcinogenicityNon-carcinogens0.8887
BiodegradationNot ready biodegradable0.9771
Rat acute toxicity2.3326 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.936
hERG inhibition (predictor II)Non-inhibitor0.6192
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 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 / Benzonitriles / Aralkylamines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Boronic acids
show 9 more
Substituents
Alpha-dipeptide / Proline or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amphetamine or derivatives / Pyrrolidine-2-carboxamide / Pyrrolidine carboxylic acid or derivatives / Benzonitrile / N-acylpyrrolidine / Aralkylamine
show 30 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrrolidinecarboxamide, nitrile, L-proline derivative, N-acylpyrrolidine, boronic acids (CHEBI:45046)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form aga...
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Trypsin-1
Molecular Weight
26557.88 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 15:31 / Updated on August 02, 2019 08:24