N-[(5R,14R)-5-AMINO-5,14-DIMETHYL-4-OXO-3-OXA-18-AZATRICYCLO[15.3.1.1~7,11~]DOCOSA-1(21),7(22),8,10,17,19-HEXAEN-19-YL]-N-METHYLMETHANESULFONAMIDE

Identification

Name
N-[(5R,14R)-5-AMINO-5,14-DIMETHYL-4-OXO-3-OXA-18-AZATRICYCLO[15.3.1.1~7,11~]DOCOSA-1(21),7(22),8,10,17,19-HEXAEN-19-YL]-N-METHYLMETHANESULFONAMIDE
Accession Number
DB07019
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: 459.602
Monoisotopic: 459.219177249
Chemical Formula
C24H33N3O4S
InChI Key
QWDOKZPZLWNULU-MZNJEOGPSA-N
InChI
InChI=1S/C24H33N3O4S/c1-17-8-10-18-6-5-7-19(12-18)15-24(2,25)23(28)31-16-20-13-21(11-9-17)26-22(14-20)27(3)32(4,29)30/h5-7,12-14,17H,8-11,15-16,25H2,1-4H3/t17-,24-/m1/s1
IUPAC Name
N-[(5R,14R)-5-amino-5,14-dimethyl-4-oxo-3-oxa-18-azatricyclo[15.3.1.1⁷,¹¹]docosa-1(21),7,9,11(22),17,19-hexaen-19-yl]-N-methylmethanesulfonamide
SMILES
[H][[email protected]@]1(C)CCC2=CC(C[[email protected]@](C)(N)C(=O)OCC3=CC(CC1)=NC(=C3)N(C)S(C)(=O)=O)=CC=C2

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBeta-secretase 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
24768527
PubChem Substance
99443490
ChemSpider
25058977
HET
35A
PDB Entries
2ph8

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 Solubility0.0017 mg/mLALOGPS
logP3.57ALOGPS
logP3.41ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)7.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area102.59 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity125.16 m3·mol-1ChemAxon
Polarizability49.71 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9967
Blood Brain Barrier-0.5351
Caco-2 permeable-0.5965
P-glycoprotein substrateNon-substrate0.5427
P-glycoprotein inhibitor INon-inhibitor0.6999
P-glycoprotein inhibitor IINon-inhibitor0.9628
Renal organic cation transporterNon-inhibitor0.8933
CYP450 2C9 substrateNon-substrate0.6309
CYP450 2D6 substrateNon-substrate0.7986
CYP450 3A4 substrateSubstrate0.5591
CYP450 1A2 substrateNon-inhibitor0.7191
CYP450 2C9 inhibitorNon-inhibitor0.7347
CYP450 2D6 inhibitorNon-inhibitor0.8814
CYP450 2C19 inhibitorNon-inhibitor0.7372
CYP450 3A4 inhibitorInhibitor0.55
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9381
Ames testNon AMES toxic0.5918
CarcinogenicityNon-carcinogens0.8652
BiodegradationNot ready biodegradable0.9657
Rat acute toxicity2.5498 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9105
hERG inhibition (predictor II)Non-inhibitor0.7583
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 alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Aralkylamines / Pyridines and derivatives / Organosulfonamides / Organic sulfonamides / Benzenoids / Imidolactams / Aminosulfonyl compounds / Heteroaromatic compounds / Carboxylic acid esters / Lactones
show 8 more
Substituents
Alpha-amino acid or derivatives / Aralkylamine / Pyridine / Organic sulfonic acid amide / Organosulfonic acid amide / Benzenoid / Imidolactam / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Peptidase activity
Specific Function
Responsible for the proteolytic processing of the amyloid precursor protein (APP). Cleaves at the N-terminus of the A-beta peptide sequence, between residues 671 and 672 of APP, leads to the genera...
Gene Name
BACE1
Uniprot ID
P56817
Uniprot Name
Beta-secretase 1
Molecular Weight
55710.28 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 15:18 / Updated on December 01, 2017 15:44