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

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
Accession Number
DB08546
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 448.4712
Monoisotopic: 448.174669898
Chemical Formula
C24H24N4O5
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-ylmethyl)-7-hydroxy-1,3-dioxo-decahydropyrrolo[3,4-a]pyrrolizin-4-yl]benzene-1-carboximidamide
SMILES
[H][[email protected]]1(O)C[[email protected]]2[[email protected]@]([H])(C1)[[email protected]]1([H])C(=O)N(CC3=CC=C4OCOC4=C3)C(=O)[[email protected]]1([H])[[email protected]]2([H])C1=CC=C(C=C1)C(N)=N

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UProthrombinNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
4369485
PubChem Substance
99445017
ChemSpider
3572029
HET
SHY
PDB Entries
1vzq

Clinical Trials

Clinical Trials
Not Available

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
Polarizability46.02 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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
2-phenylpyrrolidine / Benzodioxole / Pyrrolizidine / Aralkylamine / Monocyclic benzene moiety / Carboxylic acid imide, n-substituted / Pyrrolidone / 2-pyrrolidone / N-alkylpyrrolidine / Benzenoid
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:32 / Updated on December 01, 2017 16:06