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Identification
NameN-[(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 NumberDB07019
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 459.602
Monoisotopic: 459.219177249
Chemical FormulaC24H33N3O4S
InChI KeyInChIKey=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][C@@]1(C)CCC2=CC(C[C@@](C)(N)C(=O)OCC3=CC(CC1)=NC(=C3)N(C)S(C)(=O)=O)=CC=C2
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Aralkylamine
  • Aminopyridine
  • Imidolactam
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 generation and extracellular release of beta-cleaved soluble APP, and a corresponding cell-associated C-terminal fragment which is later released by gamma-secretase.
Gene Name:
BACE1
Uniprot ID:
P56817
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 ]
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Drug created on September 15, 2010 15:18 / Updated on September 16, 2013 18:05