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Identification
Name4-[(3AS,4R,7R,8AS,8BR)-2-(1,3-BENZODIOXOL-5-YLMETHYL)-7-HYDROXY-1,3-DIOXODECAHYDROPYRROLO[3,4-A]PYRROLIZIN-4-YL]BENZENECARBOXIMIDAMIDE
Accession NumberDB08546
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 448.4712
Monoisotopic: 448.174669898
Chemical FormulaC24H24N4O5
InChI KeyCETLUACQMGBMFH-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][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
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
ProthrombinProteinunknownNot AvailableHumanP00734 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPhenylpyrrolidines
Direct ParentPhenylpyrrolidines
Alternative Parents
Substituents
  • 2-phenylpyrrolidine
  • Benzodioxole
  • Pyrrolizidine
  • Benzylamine
  • Aralkylamine
  • Dicarboximide
  • Benzenoid
  • N-alkylpyrrolidine
  • 2-pyrrolidone
  • Pyrrolidone
  • Carboxylic acid imide, n-substituted
  • Monocyclic benzene moiety
  • Pyrrole
  • Carboxylic acid imide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Lactam
  • Carboxamide group
  • 1,2-aminoalcohol
  • Oxacycle
  • Azacycle
  • Carboximidamide
  • Carboxylic acid derivative
  • Carboxylic acid amidine
  • Amidine
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot 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 homeostasis, inflammation and wound healing.
Gene Name:
F2
Uniprot ID:
P00734
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 ]
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Drug created on September 15, 2010 15:32 / Updated on August 17, 2016 12:24