(3S,3aR,4R,4aS,8aR,9aS)-4-[(E)-2-[(2S,6R)-1,6-dimethylpiperidin-2-yl]ethenyl]-3-methyl-dodecahydronaphtho[2,3-c]furan-1-one

• ChemBase ID: 131553
• Molecular Formular: C22H35NO2
• Molecular Mass: 345.5188
• Monoisotopic Mass: 345.26677937
• SMILES: C[C@@H]1CCC[C@H](N1C)/C=C/[C@@H]1[C@H]2CCCC[C@@H]2C[C@H]2[C@@H]1[C@@H](OC2=O)C
• Canonical SMILES: C[C@@H]1OC(=O)[C@@H]2[C@H]1[C@H](/C=C/[C@@H]1CCC[C@H](N1C)C)[C@H]1CCCC[C@@H]1C2
• InChI: InChI=1S/C22H35NO2/c1-14-7-6-9-17(23(14)3)11-12-19-18-10-5-4-8-16(18)13-20-21(19)15(2)25-22(20)24/h11-12,14-21H,4-10,13H2,1-3H3/b12-11+/t14-,15+,16-,17+,18+,19-,20+,21-/m1/s1
• InChIKey: FMPNFDSPHNUFOS-YKCJDCANSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,3aR,4R,4aS,8aR,9aS)-4-[(E)-2-[(2S,6R)-1,6-dimethylpiperidin-2-yl]ethenyl]-3-methyl-dodecahydronaphtho[2,3-c]furan-1-one
• IUPAC Traditional name: himbafcine
• Synonyms: (3S,3aR,4R,4aS,8aR,9aS)-4-[(1E)-2-[(2R,6S)-1,6-dimethyl-2-piperdinyl]ethenyl]decahydro-3-methyl-naphtho[2,3-c]furan-1(3H)-one; (+)-Himbacine

Database IDs

• CAS Number: 6879-74-9
• MDL Number: MFCD00274559
• PubChem SID: 24895661; 162225831
• PubChem CID: 5281825

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.2873052
• LogD (pH = 7.4): 2.898734
• Log P: 4.467865
• Molar Refractivity: 102.2695 cm^3
• Polarizability: 40.390057 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble50 mg/mL; H2O: insoluble
• Apperance: off-white powder
• Optical Rotation: [α]/D +51.4°, c = 1.01 in chloroform(lit.)

Safety Information

• RTECS: QL0843500
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: rat ... Chrm1(25229), Chrm2(81645)

Product Information

• Purity: ~98% (GC)

DETAILS

Sigma Aldrich - H4904

Biochem/physiol Actions
Selective M2/M4 muscarinic acetylcholine receptor antagonist.
Caution
Hygroscopic