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N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide

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Overview

Structure
DrugBank ID
DB06858
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
N-cyclooctylglycyl-N-(4-carbamimidoylbenzyl)-L-prolinamide
DrugBank Accession Number
DB06858
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 413.5563
Monoisotopic: 413.279075389
Chemical Formula
C23H35N5O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProthrombinNot AvailableHumans
USerine protease 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

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 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 / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Dialkylamines / Carboximidamides / Carboxamidines
show 5 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 21 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
MMLOIDMSBRJZAE-FQEVSTJZSA-N
InChI
InChI=1S/C23H35N5O2/c24-22(25)18-12-10-17(11-13-18)15-27-23(30)20-9-6-14-28(20)21(29)16-26-19-7-4-2-1-3-5-8-19/h10-13,19-20,26H,1-9,14-16H2,(H3,24,25)(H,27,30)/t20-/m0/s1
IUPAC Name
(2S)-N-[(4-carbamimidoylphenyl)methyl]-1-[2-(cyclooctylamino)acetyl]pyrrolidine-2-carboxamide
SMILES
[H][C@]1(CCCN1C(=O)CNC1CCCCCCC1)C(=O)NCC1=CC=C(C=C1)C(N)=N

References

General References
Not Available
PubChem Compound
46937030
PubChem Substance
99443329
ChemSpider
25060816
ZINC
ZINC000039025304
PDBe Ligand
13U
PDB Entries
2zhe / 2zq2

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 Solubility0.046 mg/mLALOGPS
logP1.62ALOGPS
logP1.77Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)14.37Chemaxon
pKa (Strongest Basic)11.49Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area111.31 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity128.98 m3·mol-1Chemaxon
Polarizability48.09 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9704
Blood Brain Barrier+0.9283
Caco-2 permeable-0.7096
P-glycoprotein substrateSubstrate0.671
P-glycoprotein inhibitor INon-inhibitor0.877
P-glycoprotein inhibitor IIInhibitor0.585
Renal organic cation transporterNon-inhibitor0.5499
CYP450 2C9 substrateNon-substrate0.806
CYP450 2D6 substrateNon-substrate0.7066
CYP450 3A4 substrateNon-substrate0.6357
CYP450 1A2 substrateNon-inhibitor0.7198
CYP450 2C9 inhibitorNon-inhibitor0.8157
CYP450 2D6 inhibitorNon-inhibitor0.8359
CYP450 2C19 inhibitorNon-inhibitor0.6146
CYP450 3A4 inhibitorNon-inhibitor0.6678
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6619
Ames testNon AMES toxic0.7213
CarcinogenicityNon-carcinogens0.8995
BiodegradationNot ready biodegradable0.9612
Rat acute toxicity2.4249 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8943
hERG inhibition (predictor II)Non-inhibitor0.5484
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/MSsplash10-03xr-0343900000-025e77a51d8a3b78e795
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03ej-0931400000-a8685e819113112b7cf2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dj-0819700000-7bac461f83331574264b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03ds-3961100000-8f7ec7dc80cb2210eee7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01qc-1910000000-396122caec45238985c1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01u4-9860100000-54456dac1475f7ff33d5
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]-196.11201
predicted
DeepCCS 1.0 (2019)
[M+H]+198.537
predicted
DeepCCS 1.0 (2019)
[M+Na]+205.80055
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 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]
Details2. 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]

Drug created at September 15, 2010 21:17 / Updated at June 12, 2020 16:52