NAV

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

Identification

Generic Name
6-FLUORO-2-[2-HYDROXY-3-(2-METHYL-CYCLOHEXYLOXY)-PHENYL]-1H-INDOLE-5-CARBOXAMIDINE
DrugBank Accession Number
DB06856
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 381.4433
Monoisotopic: 381.185255232
Chemical Formula
C22H24FN3O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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 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
1-hydroxy-4-unsubstituted benzenoid / 2-phenylindole / 2-phenylpyrrole / Alkyl aryl ether / Amidine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid
show 18 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
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

References

General References
Not Available
PubChem Compound
445849
PubChem Substance
99443327
ChemSpider
393362
BindingDB
14149
ZINC
ZINC000006494961
PDBe Ligand
134
PDB Entries
1gj9

Clinical Trials

Clinical Trials
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 Solubility0.00219 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/MSsplash10-001j-9027000000-d795503a3d0b9da045f6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-0049000000-da5afb64830ceeb228b0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-015i-3093000000-106bdff0238dcf276026
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-1092000000-e467d6cc4f5747aa7a44
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0532-9001000000-0260492eafb9610e5f29
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0wmi-0093000000-a1046a276e366371b8d8
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]-190.50708
predicted
DeepCCS 1.0 (2019)
[M+H]+192.90266
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.81517
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Urokinase-type plasminogen activator
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. [Article]

Drug created at September 15, 2010 21:17 / Updated at June 12, 2020 16:52