CIS-4-METHYL-N-[(1S)-3-(METHYLSULFANYL)-1-(PYRIDIN-4-YLCARBAMOYL)PROPYL]CYCLOHEXANECARBOXAMIDE

Identification

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Name
CIS-4-METHYL-N-[(1S)-3-(METHYLSULFANYL)-1-(PYRIDIN-4-YLCARBAMOYL)PROPYL]CYCLOHEXANECARBOXAMIDE
Accession Number
DB07569
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: 349.491
Monoisotopic: 349.182397813
Chemical Formula
C18H27N3O2S
InChI Key
OCZKGSPGDOPDAI-LZWOXQAQSA-N
InChI
InChI=1S/C18H27N3O2S/c1-13-3-5-14(6-4-13)17(22)21-16(9-12-24-2)18(23)20-15-7-10-19-11-8-15/h7-8,10-11,13-14,16H,3-6,9,12H2,1-2H3,(H,21,22)(H,19,20,23)/t13-,14+,16-/m0/s1
IUPAC Name
(2S)-4-(methylsulfanyl)-N-(pyridin-4-yl)-2-{[(1s,4s)-4-methylcyclohexyl]formamido}butanamide
SMILES
[H][C@@](CCSC)(NC(=O)[C@]1([H])CC[C@]([H])(C)CC1)C(=O)NC1=CC=NC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
ULanosterol 14-alpha demethylaseNot AvailableMycobacterium tuberculosis
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
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

References

General References
Not Available
External Links
PubChem Compound
25134245
PubChem Substance
99444040
ChemSpider
26330351
HET
CM9
PDB Entries
2w09

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 Solubility0.00798 mg/mLALOGPS
logP2.15ALOGPS
logP2.51ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)12.4ChemAxon
pKa (Strongest Basic)5.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area71.09 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity98.9 m3·mol-1ChemAxon
Polarizability39.08 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.967
Blood Brain Barrier+0.8779
Caco-2 permeable-0.5252
P-glycoprotein substrateSubstrate0.7521
P-glycoprotein inhibitor INon-inhibitor0.5411
P-glycoprotein inhibitor IINon-inhibitor0.9616
Renal organic cation transporterNon-inhibitor0.7981
CYP450 2C9 substrateNon-substrate0.8174
CYP450 2D6 substrateNon-substrate0.7619
CYP450 3A4 substrateSubstrate0.5451
CYP450 1A2 substrateNon-inhibitor0.9076
CYP450 2C9 inhibitorNon-inhibitor0.715
CYP450 2D6 inhibitorNon-inhibitor0.9409
CYP450 2C19 inhibitorNon-inhibitor0.6406
CYP450 3A4 inhibitorNon-inhibitor0.6942
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9375
Ames testNon AMES toxic0.8112
CarcinogenicityNon-carcinogens0.943
BiodegradationNot ready biodegradable0.9963
Rat acute toxicity2.2974 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9502
hERG inhibition (predictor II)Non-inhibitor0.5539
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 methionine and derivatives. These are compounds containing methionine or a derivative thereof resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Methionine and derivatives
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / N-arylamides / Pyridines and derivatives / Fatty amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Sulfenyl compounds / Dialkylthioethers / Azacyclic compounds
show 4 more
Substituents
Methionine or derivatives / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / N-arylamide / Fatty amide / Pyridine / Fatty acyl / Heteroaromatic compound / Carboxamide group / Secondary carboxylic acid amide
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Sterol 14-demethylase activity
Specific Function
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name
ERG11
Uniprot ID
P10614
Uniprot Name
Lanosterol 14-alpha demethylase
Molecular Weight
60719.765 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 15:23 / Updated on December 02, 2019 07:47