6-fluoro-2-(2-hydroxy-3-isobutoxy-phenyl)-1H-benzoimidazole-5-carboxamidine

Identification

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Name
6-fluoro-2-(2-hydroxy-3-isobutoxy-phenyl)-1H-benzoimidazole-5-carboxamidine
Accession Number
DB06855  (EXPT00343, DB03494)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
CRA 10950 / CRA-10950
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 342.3675
Monoisotopic: 342.149204077
Chemical Formula
C18H19FN4O2
InChI Key
NSUDDASMRZSVON-UHFFFAOYSA-N
InChI
InChI=1S/C18H19FN4O2/c1-9(2)8-25-15-5-3-4-10(16(15)24)18-22-13-6-11(17(20)21)12(19)7-14(13)23-18/h3-7,9,24H,8H2,1-2H3,(H3,20,21)(H,22,23)
IUPAC Name
2-{5-[amino(iminiumyl)methyl]-6-fluoro-1H-1,3-benzodiazol-2-yl}-6-(2-methylpropoxy)benzen-1-olate
SMILES
CC(C)COC1=C(O)C(=CC=C1)C1=NC2=CC(C(N)=N)=C(F)C=C2N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUrokinase-type plasminogen activatorNot AvailableHumans
UTrypsin-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
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
6102526
PubChem Substance
99443326
ChemSpider
20120240
BindingDB
14148
ChEMBL
CHEMBL62836
HET
950
PDB Entries
1gj8 / 1o2o

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 Solubility0.00657 mg/mLALOGPS
logP1.7ALOGPS
logP2.8ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.58 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.5 m3·mol-1ChemAxon
Polarizability36.52 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9911
Blood Brain Barrier+0.9062
Caco-2 permeable-0.6074
P-glycoprotein substrateSubstrate0.6607
P-glycoprotein inhibitor INon-inhibitor0.8252
P-glycoprotein inhibitor IIInhibitor0.8223
Renal organic cation transporterNon-inhibitor0.6815
CYP450 2C9 substrateNon-substrate0.7597
CYP450 2D6 substrateNon-substrate0.7822
CYP450 3A4 substrateNon-substrate0.5193
CYP450 1A2 substrateInhibitor0.726
CYP450 2C9 inhibitorNon-inhibitor0.6188
CYP450 2D6 inhibitorNon-inhibitor0.6097
CYP450 2C19 inhibitorInhibitor0.5873
CYP450 3A4 inhibitorNon-inhibitor0.5272
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.784
Ames testNon AMES toxic0.5542
CarcinogenicityNon-carcinogens0.8679
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5648 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9937
hERG inhibition (predictor II)Inhibitor0.5257
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 phenylbenzimidazoles. These are compounds containing a phenylbenzimidazole skeleton, which consists of a benzimidazole moiety where its imidazole ring is attached to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Phenylbenzimidazoles
Direct Parent
Phenylbenzimidazoles
Alternative Parents
Phenylimidazoles / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / Aryl fluorides / Heteroaromatic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds
show 3 more
Substituents
Phenylbenzimidazole / 2-phenylimidazole / Phenoxy compound / Phenol ether / Alkyl aryl ether / 1-hydroxy-4-unsubstituted benzenoid / Phenol / Aryl fluoride / Aryl halide / Monocyclic benzene moiety
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Specifically cleaves the zymogen plasminogen to form the active enzyme plasmin.
Gene Name
PLAU
Uniprot ID
P00749
Uniprot Name
Urokinase-type plasminogen activator
Molecular Weight
48507.09 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]
Details
2. Trypsin-1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific 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 aga...
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Trypsin-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. [PubMed:10592235]

Drug created on September 15, 2010 15:17 / Updated on August 02, 2019 07:56