NAV

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

Generic 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
DrugBank Accession Number
DB07019
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 459.602
Monoisotopic: 459.219177249
Chemical Formula
C24H33N3O4S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-secretase 1Not 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 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 / Amine / Aminosulfonyl compound / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid ester / Heteroaromatic compound
show 21 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
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[15.3.1.1^{7,11}]docosa-1(21),7,9,11(22),17,19-hexaen-19-yl]-N-methylmethanesulfonamide
SMILES
[H][C@@]1(C)CCC2=CC(C[C@@](C)(N)C(=O)OCC3=CC(CC1)=NC(=C3)N(C)S(C)(=O)=O)=CC=C2

References

General References
Not Available
PubChem Compound
24768527
PubChem Substance
99443490
ChemSpider
25058977
ZINC
ZINC000016052369
PDBe Ligand
35A
PDB Entries
2ph8

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 Solubility0.0017 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-MSsplash10-001i-0009200000-2f2e1ba5b358ea80c63b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-0000900000-14bc254557f2efba58b9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1000900000-224fea475eccb68887c8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-02tc-0008900000-e3f4f634b43c9861d02c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6r-6201900000-5b5e8a13878b57b9d22a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gc0-1009000000-bce28bf676c817f255b4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9105000000-bb809546c4125fc5f7b9
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]-201.541
predicted
DeepCCS 1.0 (2019)
[M+H]+203.93657
predicted
DeepCCS 1.0 (2019)
[M+Na]+209.84908
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-secretase 1
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:18 / Updated at June 12, 2020 16:52