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(S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide

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Overview

Structure
DrugBank ID
DB07131
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
(S)-N-(4-carbamimidoylbenzyl)-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide
DrugBank Accession Number
DB07131
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 384.5151
Monoisotopic: 384.252526288
Chemical Formula
C22H32N4O2
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
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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 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 / Carboximidamides / Carboxamidines / Azacyclic compounds / Organopnictogen compounds
show 3 more
Substituents
Alpha-amino acid amide / Amidine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboximidamide / Carboxylic acid amidine / Hydrocarbon derivative
show 15 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
DOTBZTLJSXFKCP-IBGZPJMESA-N
InChI
InChI=1S/C22H32N4O2/c23-21(24)18-11-8-17(9-12-18)15-25-22(28)19-7-4-14-26(19)20(27)13-10-16-5-2-1-3-6-16/h8-9,11-12,16,19H,1-7,10,13-15H2,(H3,23,24)(H,25,28)/t19-/m0/s1
IUPAC Name
(2S)-N-[(4-carbamimidoylphenyl)methyl]-1-(3-cyclohexylpropanoyl)pyrrolidine-2-carboxamide
SMILES
[H][C@]1(CCCN1C(=O)CCC1CCCCC1)C(=O)NCC1=CC=C(C=C1)C(N)=N

References

General References
Not Available
PubChem Compound
25134248
PubChem Substance
99443602
ChemSpider
25049922
BindingDB
50307868
ChEMBL
CHEMBL1198138
ZINC
ZINC000039018741
PDBe Ligand
50U
PDB Entries
2zdk / 2zg0

Clinical Trials

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 Solubility0.031 mg/mLALOGPS
logP2.87ALOGPS
logP2.32Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)14.45Chemaxon
pKa (Strongest Basic)11.48Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area99.28 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity121.01 m3·mol-1Chemaxon
Polarizability44.01 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9506
Blood Brain Barrier+0.8826
Caco-2 permeable-0.7306
P-glycoprotein substrateSubstrate0.6815
P-glycoprotein inhibitor INon-inhibitor0.7466
P-glycoprotein inhibitor IINon-inhibitor0.6688
Renal organic cation transporterInhibitor0.6839
CYP450 2C9 substrateNon-substrate0.7822
CYP450 2D6 substrateNon-substrate0.6968
CYP450 3A4 substrateNon-substrate0.6413
CYP450 1A2 substrateNon-inhibitor0.8307
CYP450 2C9 inhibitorNon-inhibitor0.6707
CYP450 2D6 inhibitorNon-inhibitor0.8287
CYP450 2C19 inhibitorInhibitor0.5157
CYP450 3A4 inhibitorNon-inhibitor0.5218
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6512
Ames testNon AMES toxic0.7628
CarcinogenicityNon-carcinogens0.9001
BiodegradationNot ready biodegradable0.9606
Rat acute toxicity2.3983 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9058
hERG inhibition (predictor II)Inhibitor0.5878
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-0249000000-828e0ae1c11080fe3384
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0925000000-f33a4e061988b0632499
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-0409000000-53bbdc161db4c541398d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-053g-5696000000-8240ab47d89fec4d54a5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0089-2941000000-868e14d70d50ed3ca628
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-6931000000-cb39bfcf1dee3edf8538
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]-187.32205
predicted
DeepCCS 1.0 (2019)
[M+H]+189.68005
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.56569
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 21:19 / Updated at June 12, 2020 16:52