(1S,3R,4S,5S,7S)-4-{[2-(4-METHOXYPHENOXY)-2-METHYLPROPANOYL]AMINO}ADAMANTANE-1-CARBOXAMIDE

Identification

Name
(1S,3R,4S,5S,7S)-4-{[2-(4-METHOXYPHENOXY)-2-METHYLPROPANOYL]AMINO}ADAMANTANE-1-CARBOXAMIDE
Accession Number
DB08280
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: 386.4846
Monoisotopic: 386.220557458
Chemical Formula
C22H30N2O4
InChI Key
MNVKIDPRYUGTTG-YINOZDTMSA-N
InChI
InChI=1S/C22H30N2O4/c1-21(2,28-17-6-4-16(27-3)5-7-17)20(26)24-18-14-8-13-9-15(18)12-22(10-13,11-14)19(23)25/h4-7,13-15,18H,8-12H2,1-3H3,(H2,23,25)(H,24,26)/t13-,14-,15+,18-,22-
IUPAC Name
(1s,3R,4s,5S,7s)-4-[2-(4-methoxyphenoxy)-2-methylpropanamido]adamantane-1-carboxamide
SMILES
[H][[email protected]@]12C[[email protected]@]3([H])C[[email protected]@](C1)(C[[email protected]@]([H])(C2)[[email protected]@]3([H])NC(=O)C(C)(C)OC1=CC=C(OC)C=C1)C(N)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCorticosteroid 11-beta-dehydrogenase isozyme 1Not AvailableHuman
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
15942677
PubChem Substance
99444751
ChemSpider
26328288
HET
NN4
PDB Entries
2irw

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 Solubility0.0117 mg/mLALOGPS
logP2.84ALOGPS
logP2.41ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)14.84ChemAxon
pKa (Strongest Basic)0.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.65 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.46 m3·mol-1ChemAxon
Polarizability42.32 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9875
Blood Brain Barrier-0.532
Caco-2 permeable-0.6224
P-glycoprotein substrateSubstrate0.5264
P-glycoprotein inhibitor INon-inhibitor0.6845
P-glycoprotein inhibitor IIInhibitor0.5569
Renal organic cation transporterNon-inhibitor0.9406
CYP450 2C9 substrateNon-substrate0.8427
CYP450 2D6 substrateNon-substrate0.8001
CYP450 3A4 substrateSubstrate0.6545
CYP450 1A2 substrateNon-inhibitor0.8352
CYP450 2C9 inhibitorNon-inhibitor0.6939
CYP450 2D6 inhibitorNon-inhibitor0.9424
CYP450 2C19 inhibitorNon-inhibitor0.8079
CYP450 3A4 inhibitorNon-inhibitor0.7223
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7394
Ames testNon AMES toxic0.6802
CarcinogenicityNon-carcinogens0.8633
BiodegradationNot ready biodegradable0.9918
Rat acute toxicity2.3978 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9983
hERG inhibition (predictor II)Non-inhibitor0.8441
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Anisoles
Direct Parent
Anisoles
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Alkyl aryl ethers / Secondary carboxylic acid amides / Primary carboxylic acid amides / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Phenoxy compound / Anisole / Methoxybenzene / Alkyl aryl ether / Monocyclic benzene moiety / Carboxamide group / Secondary carboxylic acid amide / Primary carboxylic acid amide / Carboxylic acid derivative / Ether
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
11-beta-hydroxysteroid dehydrogenase [nad(p)] activity
Specific Function
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the rea...
Gene Name
HSD11B1
Uniprot ID
P28845
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 1
Molecular Weight
32400.665 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 15:30 / Updated on December 01, 2017 16:02