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

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Identification

Generic Name
(S)-N-(4-carbamimidoylbenzyl)-1-(2-(cyclohexylamino)ethanoyl)pyrrolidine-2-carboxamide
DrugBank Accession Number
DB06850
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 385.5031
Monoisotopic: 385.247775261
Chemical Formula
C21H31N5O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USerine protease 1Not AvailableHumans
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 / Pyrrolidinecarboxamides / N-acylpyrrolidines / Cyclohexylamines / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Azacyclic compounds / Carboxamidines
show 6 more
Substituents
Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amidine / Amine / Amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group
show 22 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
RYKFVFFOIYLADT-SFHVURJKSA-N
InChI
InChI=1S/C21H31N5O2/c22-20(23)16-10-8-15(9-11-16)13-25-21(28)18-7-4-12-26(18)19(27)14-24-17-5-2-1-3-6-17/h8-11,17-18,24H,1-7,12-14H2,(H3,22,23)(H,25,28)/t18-/m0/s1
IUPAC Name
(2S)-N-[(4-carbamimidoylphenyl)methyl]-1-[2-(cyclohexylamino)acetyl]pyrrolidine-2-carboxamide
SMILES
[H][C@]1(CCCN1C(=O)CNC1CCCCC1)C(=O)NCC1=CC=C(C=C1)C(N)=N

References

General References
Not Available
PubChem Compound
44141860
PubChem Substance
99443321
ChemSpider
25060602
ZINC
ZINC000039035255
PDBe Ligand
11U
PDB Entries
2zq1 / 3biv / 3ljo

Clinical Trials

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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 Solubility0.137 mg/mLALOGPS
logP0.85ALOGPS
logP0.88Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)14.42Chemaxon
pKa (Strongest Basic)11.49Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area111.31 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity119.78 m3·mol-1Chemaxon
Polarizability43.07 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9293
Blood Brain Barrier+0.8697
Caco-2 permeable-0.698
P-glycoprotein substrateSubstrate0.7014
P-glycoprotein inhibitor INon-inhibitor0.7354
P-glycoprotein inhibitor IIInhibitor0.5577
Renal organic cation transporterInhibitor0.5731
CYP450 2C9 substrateNon-substrate0.759
CYP450 2D6 substrateNon-substrate0.7065
CYP450 3A4 substrateNon-substrate0.6123
CYP450 1A2 substrateNon-inhibitor0.8457
CYP450 2C9 inhibitorNon-inhibitor0.685
CYP450 2D6 inhibitorNon-inhibitor0.7769
CYP450 2C19 inhibitorNon-inhibitor0.5
CYP450 3A4 inhibitorInhibitor0.5605
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6646
Ames testNon AMES toxic0.7641
CarcinogenicityNon-carcinogens0.8817
BiodegradationNot ready biodegradable0.9073
Rat acute toxicity2.4298 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9074
hERG inhibition (predictor II)Inhibitor0.7086
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/MSsplash10-000i-0139000000-518e8b1a4981e7dc2232
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0916000000-3ebfca52e121cc25e6ae
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-1309000000-1d0bb036c3cc15f7e177
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01pw-4974000000-211c74e56a7a043e1b50
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-3921000000-e7cfef7862a50294633a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lv-9631000000-53c470205ac785e1e237
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]-187.14409
predicted
DeepCCS 1.0 (2019)
[M+H]+189.50209
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.38164
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Serine protease 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General 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 against all of these substrates
Specific Function
Metal ion binding
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Serine protease 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. [Article]
Details2. Prothrombin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General 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 homeostasis, inflammation and wound healing. Thrombin triggers the production of pro-inflammatory cytokines, such as MCP-1/CCL2 and IL8/CXCL8, in endothelial cells (PubMed:30568593, PubMed:9780208)
Specific Function
Calcium ion binding
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 21:17 / Updated at June 12, 2020 16:52