(1S,16S)-16-methoxy-5-oxa-10-azatetracyclo[8.7.0.01,13.02,7]heptadeca-2(7),13-dien-4-one hydrobromide

• ChemBase ID: 131416
• Molecular Formular: C16H22BrNO3
• Molecular Mass: 356.25478
• Monoisotopic Mass: 355.07830557
• SMILES: CO[C@H]1CC=C2CCN3[C@]2(C1)C1=C(CC3)COC(=O)C1.Br
• Canonical SMILES: CO[C@H]1CC=C2[C@]3(C1)N(CC2)CCC1=C3CC(=O)OC1.Br
• InChI: InChI=1S/C16H21NO3.BrH/c1-19-13-3-2-12-5-7-17-6-4-11-10-20-15(18)8-14(11)16(12,17)9-13;/h2,13H,3-10H2,1H3;1H/t13-,16-;/m0./s1
• InChIKey: GFIGWAJEIMHJJB-LINSIKMZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,16S)-16-methoxy-5-oxa-10-azatetracyclo[8.7.0.0^1,^1^3.0^2,^7]heptadeca-2(7),13-dien-4-one hydrobromide
• IUPAC Traditional name: dihydro β erythroidine hydrobromide
• Synonyms: 3β-1,6-Didehydro-14,17-dihydro-3-methoxy-16(15H)-oxaerythrinan-15-one hydrobromide; Dihydro-β-erythroidine hydrobromide

Database IDs

• CAS Number: 29734-68-7
• MDL Number: MFCD00153793
• PubChem SID: 24278808; 162225694
• PubChem CID: 11957537

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -2.927037
• LogD (pH = 7.4): -1.3592727
• Log P: 0.29973823
• Molar Refractivity: 76.9995 cm^3
• Polarizability: 29.788475 Å^3
• Polar Surface Area: 38.77 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble5 mg/mL; H2O: soluble800 mg/mL
• Apperance: white solid
• Optical Rotation: [α]22/D +99.2°, c = 0.90 in H2O(lit.)

Safety Information

• RTECS: KF3325000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... CHRNA1(1134), CHRNA10(57053), CHRNA2(1135), CHRNA3(1136), CHRNA4(1137), CHRNA5(1138), CHRNA6(8973), CHRNA7(1139), CHRNA9(55584), CHRNB1(1140), CHRNB2(1141), CHRNB3(1142), CHRNB4(1143)

DETAILS

Sigma Aldrich - D149

Biochem/physiol Actions
Competitive nicotinic receptor antagonist.