6-FLUORO-2-[2-HYDROXY-3-(2-METHYL-CYCLOHEXYLOXY)-PHENYL]-1H-INDOLE-5-CARBOXAMIDINE

Identification

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Name
6-FLUORO-2-[2-HYDROXY-3-(2-METHYL-CYCLOHEXYLOXY)-PHENYL]-1H-INDOLE-5-CARBOXAMIDINE
Accession Number
DB06856
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: 381.4433
Monoisotopic: 381.185255232
Chemical Formula
C22H24FN3O2
InChI Key
HUYQYLFFFNSAAX-BUXKBTBVSA-N
InChI
InChI=1S/C22H24FN3O2/c1-12-5-2-3-7-19(12)28-20-8-4-6-14(21(20)27)18-10-13-9-15(22(24)25)16(23)11-17(13)26-18/h4,6,8-12,19,26-27H,2-3,5,7H2,1H3,(H3,24,25)/t12-,19-/m0/s1
IUPAC Name
6-fluoro-2-(2-hydroxy-3-{[(1S,2S)-2-methylcyclohexyl]oxy}phenyl)-1H-indole-5-carboximidamide
SMILES
[H][C@]1(C)CCCC[C@]1([H])OC1=C(O)C(=CC=C1)C1=CC2=CC(C(N)=N)=C(F)C=C2N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UUrokinase-type plasminogen activatorNot 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
445849
PubChem Substance
99443327
ChemSpider
393362
BindingDB
14149
HET
134
PDB Entries
1gj9

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 Solubility0.00219 mg/mLALOGPS
logP4.33ALOGPS
logP4.01ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)9.78ChemAxon
pKa (Strongest Basic)9.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area95.12 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity117.98 m3·mol-1ChemAxon
Polarizability41.96 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.996
Blood Brain Barrier+0.9192
Caco-2 permeable-0.5758
P-glycoprotein substrateSubstrate0.6395
P-glycoprotein inhibitor INon-inhibitor0.8251
P-glycoprotein inhibitor IIInhibitor0.5952
Renal organic cation transporterNon-inhibitor0.648
CYP450 2C9 substrateNon-substrate0.7031
CYP450 2D6 substrateNon-substrate0.7561
CYP450 3A4 substrateNon-substrate0.5165
CYP450 1A2 substrateInhibitor0.5935
CYP450 2C9 inhibitorNon-inhibitor0.5844
CYP450 2D6 inhibitorNon-inhibitor0.6986
CYP450 2C19 inhibitorInhibitor0.6444
CYP450 3A4 inhibitorNon-inhibitor0.6446
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7649
Ames testNon AMES toxic0.6135
CarcinogenicityNon-carcinogens0.8834
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6965 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9626
hERG inhibition (predictor II)Inhibitor0.6615
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 2-phenylindoles. These are indoles substituted at the 2-position with a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
2-phenylindoles
Alternative Parents
Phenylpyrroles / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / Aryl fluorides / Heteroaromatic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds
show 3 more
Substituents
2-phenylindole / 2-phenylpyrrole / 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]

Drug created on September 15, 2010 15:17 / Updated on June 04, 2019 06:30