NAV

4-Oxo-2-Phenylmethanesulfonyl-Octahydro-Pyrrolo[1,2-a]Pyrazine-6-Carboxylic Acid [1-(N-Hydroxycarbamimidoyl)-Piperidin-4-Ylmethyl]-Amide

Identification

Generic Name
4-Oxo-2-Phenylmethanesulfonyl-Octahydro-Pyrrolo[1,2-a]Pyrazine-6-Carboxylic Acid [1-(N-Hydroxycarbamimidoyl)-Piperidin-4-Ylmethyl]-Amide
DrugBank Accession Number
DB02723
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 492.592
Monoisotopic: 492.215488854
Chemical Formula
C22H32N6O5S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
Alpha amino acid amides / Pyrrolidinecarboxamides / N-alkylpiperazines / Piperidines / Organosulfonamides / Organic sulfonamides / N-hydroxyguanidines / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Sulfonyls
show 7 more
Substituents
1,4-diazinane / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Guanidine
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid amide, N-acylpiperidine, sulfonamide, guanidines, pyrrolopyrazine (CHEBI:41126)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DHTSUHWLPAEEQB-OALUTQOASA-N
InChI
InChI=1S/C22H32N6O5S/c23-22(25-31)26-10-8-16(9-11-26)12-24-21(30)19-7-6-18-13-27(14-20(29)28(18)19)34(32,33)15-17-4-2-1-3-5-17/h1-5,16,18-19,31H,6-15H2,(H2,23,25)(H,24,30)/t18-,19-/m0/s1
IUPAC Name
(6S,8aS)-N-({1-[(E)-N'-hydroxycarbamimidoyl]piperidin-4-yl}methyl)-4-oxo-2-phenylmethanesulfonyl-octahydropyrrolo[1,2-a]pyrazine-6-carboxamide
SMILES
O\N=C(/N)N1CCC(CC1)CNC(=O)[C@@H]1CC[C@H]2CN(CC(=O)N12)S(=O)(=O)CC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
5326608
PubChem Substance
46504445
ChemSpider
4483986
BindingDB
50107064
ChEMBL
CHEMBL18136
ZINC
ZINC000015627006
PDBe Ligand
BLI
PDB Entries
1jwt

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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 Solubility1.06 mg/mLALOGPS
logP-0.02ALOGPS
logP-1.1Chemaxon
logS-2.7ALOGPS
pKa (Strongest Acidic)13.15Chemaxon
pKa (Strongest Basic)7.29Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area148.64 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity125.65 m3·mol-1Chemaxon
Polarizability50.4 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8506
Blood Brain Barrier+0.5495
Caco-2 permeable-0.7361
P-glycoprotein substrateSubstrate0.8052
P-glycoprotein inhibitor INon-inhibitor0.7405
P-glycoprotein inhibitor IINon-inhibitor0.9772
Renal organic cation transporterNon-inhibitor0.585
CYP450 2C9 substrateNon-substrate0.736
CYP450 2D6 substrateNon-substrate0.7855
CYP450 3A4 substrateSubstrate0.5084
CYP450 1A2 substrateNon-inhibitor0.8654
CYP450 2C9 inhibitorNon-inhibitor0.8248
CYP450 2D6 inhibitorNon-inhibitor0.8804
CYP450 2C19 inhibitorNon-inhibitor0.778
CYP450 3A4 inhibitorNon-inhibitor0.9176
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9779
Ames testNon AMES toxic0.5966
CarcinogenicityNon-carcinogens0.7851
BiodegradationNot ready biodegradable0.9825
Rat acute toxicity2.4763 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7929
hERG inhibition (predictor II)Inhibitor0.5871
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/MSsplash10-0006-0002900000-2d3b84cee5f9f597f6be
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0000900000-64d8396883bfb0335a70
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-1125900000-8d0b55418f9e9f71a634
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0100900000-30c2f6b51d4eda591565
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00lu-1247900000-b472f537ea05482300b4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0076-1912300000-5aecde670ef6edca891b
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]-207.00148
predicted
DeepCCS 1.0 (2019)
[M+H]+209.39703
predicted
DeepCCS 1.0 (2019)
[M+Na]+215.38124
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Prothrombin
Kind
Protein
Organism
Humans
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:45