(S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexyloxy)ethanoyl)pyrrolidine-2-carboxamide

Identification

Name
(S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexyloxy)ethanoyl)pyrrolidine-2-carboxamide
Accession Number
DB07091
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: 386.4879
Monoisotopic: 386.231790846
Chemical Formula
C21H30N4O3
InChI Key
IWPMQJKXKKKSEY-SFHVURJKSA-N
InChI
InChI=1S/C21H30N4O3/c22-20(23)16-10-8-15(9-11-16)13-24-21(27)18-7-4-12-25(18)19(26)14-28-17-5-2-1-3-6-17/h8-11,17-18H,1-7,12-14H2,(H3,22,23)(H,24,27)/t18-/m0/s1
IUPAC Name
(2S)-N-[(4-carbamimidoylphenyl)methyl]-1-[2-(cyclohexyloxy)acetyl]pyrrolidine-2-carboxamide
SMILES
[H][[email protected]]1(CCCN1C(=O)COC1CCCCC1)C(=O)NCC1=CC=C(C=C1)C(N)=N

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTrypsin-1Not AvailableHuman
UProthrombinNot AvailableHuman
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
24963036
PubChem Substance
99443562
ChemSpider
25060896
HET
46U
PDB Entries
2zdm / 2zfr

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 Solubility0.114 mg/mLALOGPS
logP1.24ALOGPS
logP1.2ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)15.17ChemAxon
pKa (Strongest Basic)11.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area108.51 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity118.1 m3·mol-1ChemAxon
Polarizability43.05 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9688
Blood Brain Barrier+0.8907
Caco-2 permeable-0.7843
P-glycoprotein substrateSubstrate0.753
P-glycoprotein inhibitor INon-inhibitor0.5815
P-glycoprotein inhibitor IIInhibitor0.6976
Renal organic cation transporterInhibitor0.6617
CYP450 2C9 substrateNon-substrate0.7939
CYP450 2D6 substrateNon-substrate0.8037
CYP450 3A4 substrateNon-substrate0.5611
CYP450 1A2 substrateNon-inhibitor0.8604
CYP450 2C9 inhibitorNon-inhibitor0.7042
CYP450 2D6 inhibitorNon-inhibitor0.8966
CYP450 2C19 inhibitorInhibitor0.5298
CYP450 3A4 inhibitorNon-inhibitor0.8448
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6844
Ames testNon AMES toxic0.7343
CarcinogenicityNon-carcinogens0.9057
BiodegradationNot ready biodegradable0.9656
Rat acute toxicity2.3086 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9672
hERG inhibition (predictor II)Inhibitor0.665
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 proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Proline and derivatives
Alternative Parents
Alpha amino acid amides / Pyrrolidinecarboxamides / N-acylpyrrolidines / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Dialkyl ethers / Carboximidamides / Carboxamidines / Azacyclic compounds
show 4 more
Substituents
Proline or derivatives / Alpha-amino acid amide / N-acylpyrrolidine / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Monocyclic benzene moiety / Benzenoid / Pyrrolidine / Tertiary carboxylic acid amide / Carboxamide group
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:18 / Updated on December 01, 2017 15:46