NAV

(4R)-4-(3-HYDROXYPHENYL)-N,N,7,8-TETRAMETHYL-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXAMIDE

Identification

Generic Name
(4R)-4-(3-HYDROXYPHENYL)-N,N,7,8-TETRAMETHYL-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXAMIDE
DrugBank Accession Number
DB07064
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 324.4168
Monoisotopic: 324.183778022
Chemical Formula
C20H24N2O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UKinesin-like protein KIF11Not 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 4-phenyltetrahydroisoquinolines. These are compounds containing a phenyl group attached to the C4-atom of a tetrahydroisoquinoline moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Tetrahydroisoquinolines
Sub Class
4-phenyltetrahydroisoquinolines
Direct Parent
4-phenyltetrahydroisoquinolines
Alternative Parents
1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Ureas / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 4-phenyltetrahydroisoquinoline / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonic acid derivative / Carbonyl group / Hydrocarbon derivative / Monocyclic benzene moiety
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
HPVCRUIDFODATB-LJQANCHMSA-N
InChI
InChI=1S/C20H24N2O2/c1-13-8-9-17-18(14(13)2)11-22(20(24)21(3)4)12-19(17)15-6-5-7-16(23)10-15/h5-10,19,23H,11-12H2,1-4H3/t19-/m1/s1
IUPAC Name
(4R)-4-(3-hydroxyphenyl)-N,N,7,8-tetramethyl-1,2,3,4-tetrahydroisoquinoline-2-carboxamide
SMILES
[H][C@@]1(CN(CC2=C1C=CC(C)=C2C)C(=O)N(C)C)C1=CC(O)=CC=C1

References

General References
Not Available
PubChem Compound
6857690
PubChem Substance
99443535
ChemSpider
5257024
BindingDB
24127
ChEMBL
CHEMBL205786
ZINC
ZINC000013986710
PDBe Ligand
3QC
PDB Entries
2fme

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 Solubility0.101 mg/mLALOGPS
logP3.25ALOGPS
logP3.52Chemaxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.44Chemaxon
pKa (Strongest Basic)-1.6Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area43.78 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity97.28 m3·mol-1Chemaxon
Polarizability36.56 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9767
Caco-2 permeable+0.6677
P-glycoprotein substrateSubstrate0.6692
P-glycoprotein inhibitor INon-inhibitor0.6632
P-glycoprotein inhibitor IINon-inhibitor0.5312
Renal organic cation transporterNon-inhibitor0.6524
CYP450 2C9 substrateNon-substrate0.7093
CYP450 2D6 substrateNon-substrate0.6243
CYP450 3A4 substrateSubstrate0.6839
CYP450 1A2 substrateNon-inhibitor0.5428
CYP450 2C9 inhibitorNon-inhibitor0.7305
CYP450 2D6 inhibitorNon-inhibitor0.8896
CYP450 2C19 inhibitorNon-inhibitor0.7314
CYP450 3A4 inhibitorNon-inhibitor0.7285
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6856
Ames testNon AMES toxic0.6051
CarcinogenicityNon-carcinogens0.8891
BiodegradationNot ready biodegradable0.876
Rat acute toxicity2.7558 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.858
hERG inhibition (predictor II)Inhibitor0.6362
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/MSsplash10-0fb9-4059000000-b87121c784412368fdd5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fk9-0069000000-c4572a0ca22fb368aa87
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f79-1090000000-d6f504b093b02ce3ef7a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-0089000000-875fc4163b207494472a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fe0-2691000000-51227551b0c25aba430a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-5790000000-5ce5a5033ec4100a8337
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]-174.00626
predicted
DeepCCS 1.0 (2019)
[M+H]+176.36426
predicted
DeepCCS 1.0 (2019)
[M+Na]+182.7621
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Kinesin-like protein KIF11
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein kinase binding
Specific Function
Motor protein required for establishing a bipolar spindle. Blocking of KIF11 prevents centrosome migration and arrest cells in mitosis with monoastral microtubule arrays.
Gene Name
KIF11
Uniprot ID
P52732
Uniprot Name
Kinesin-like protein KIF11
Molecular Weight
119158.025 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 21:18 / Updated at June 12, 2020 16:52