NAV

4-[(3AS,4R,7R,8AS,8BR)-2-(1,3-BENZODIOXOL-5-YLMETHYL)-7-HYDROXY-1,3-DIOXODECAHYDROPYRROLO[3,4-A]PYRROLIZIN-4-YL]BENZENECARBOXIMIDAMIDE

Identification

Generic Name
4-[(3AS,4R,7R,8AS,8BR)-2-(1,3-BENZODIOXOL-5-YLMETHYL)-7-HYDROXY-1,3-DIOXODECAHYDROPYRROLO[3,4-A]PYRROLIZIN-4-YL]BENZENECARBOXIMIDAMIDE
DrugBank Accession Number
DB08546
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 448.4712
Monoisotopic: 448.174669898
Chemical Formula
C24H24N4O5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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 phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolidines
Sub Class
Phenylpyrrolidines
Direct Parent
Phenylpyrrolidines
Alternative Parents
Benzodioxoles / Pyrrolizidines / Aralkylamines / Pyrrolidine-2-ones / Benzene and substituted derivatives / N-substituted carboxylic acid imides / N-alkylpyrrolidines / Pyrroles / Dicarboximides / Trialkylamines
show 13 more
Substituents
1,2-aminoalcohol / 2-phenylpyrrolidine / 2-pyrrolidone / Acetal / Alcohol / Amidine / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
CETLUACQMGBMFH-ZALSBGIRSA-N
InChI
InChI=1S/C24H24N4O5/c25-22(26)14-4-2-13(3-5-14)21-20-19(16-8-15(29)10-27(16)21)23(30)28(24(20)31)9-12-1-6-17-18(7-12)33-11-32-17/h1-7,15-16,19-21,29H,8-11H2,(H3,25,26)/t15-,16+,19+,20+,21+/m1/s1
IUPAC Name
4-[(3aS,4R,7R,8aS,8bR)-2-[(2H-1,3-benzodioxol-5-yl)methyl]-7-hydroxy-1,3-dioxo-decahydropyrrolo[3,4-a]pyrrolizin-4-yl]benzene-1-carboximidamide
SMILES
[H][C@]1(O)C[N@]2[C@@]([H])(C1)[C@]1([H])C(=O)N(CC3=CC=C4OCOC4=C3)C(=O)[C@]1([H])[C@]2([H])C1=CC=C(C=C1)C(N)=N

References

General References
Not Available
PubChem Compound
4369485
PubChem Substance
99445017
ChemSpider
3572029
ZINC
ZINC000016051594
PDBe Ligand
SHY
PDB Entries
1vzq

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 Solubility0.1 mg/mLALOGPS
logP0.58ALOGPS
logP0.35Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.83Chemaxon
pKa (Strongest Basic)11.48Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area129.18 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity128.21 m3·mol-1Chemaxon
Polarizability45.37 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9147
Blood Brain Barrier+0.7882
Caco-2 permeable-0.7342
P-glycoprotein substrateSubstrate0.6351
P-glycoprotein inhibitor INon-inhibitor0.9511
P-glycoprotein inhibitor IINon-inhibitor0.7016
Renal organic cation transporterNon-inhibitor0.7715
CYP450 2C9 substrateNon-substrate0.8013
CYP450 2D6 substrateNon-substrate0.8334
CYP450 3A4 substrateNon-substrate0.5332
CYP450 1A2 substrateNon-inhibitor0.7674
CYP450 2C9 inhibitorNon-inhibitor0.8119
CYP450 2D6 inhibitorNon-inhibitor0.8126
CYP450 2C19 inhibitorNon-inhibitor0.7789
CYP450 3A4 inhibitorNon-inhibitor0.6712
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.879
Ames testNon AMES toxic0.6165
CarcinogenicityNon-carcinogens0.7666
BiodegradationNot ready biodegradable0.9693
Rat acute toxicity2.3001 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9961
hERG inhibition (predictor II)Non-inhibitor0.749
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/MSsplash10-0002-0000900000-844451c4f98b1e0b0940
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0000900000-c77afe083294c027decb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0000900000-bb121a1d63d29678932f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kb-0000900000-37a55df91252ec661ede
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00m0-0530900000-92837883504aa461a3f7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00l2-4356900000-9506ceb26b0f932f1f33
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]-198.06902
predicted
DeepCCS 1.0 (2019)
[M+H]+199.96443
predicted
DeepCCS 1.0 (2019)
[M+Na]+205.83925
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. 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 21:32 / Updated at June 12, 2020 16:52