(1R,9R,10S,13R)-3,4-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-10,13-diol

• ChemBase ID: 127194
• Molecular Formular: C19H27NO4
• Molecular Mass: 333.42198
• Monoisotopic Mass: 333.19400835
• SMILES: CN1CC[C@]23C[C@@H](CC[C@]2([C@H]1Cc1c3c(c(cc1)OC)OC)O)O
• Canonical SMILES: COc1c(OC)ccc2c1[C@@]13CCN([C@H](C2)[C@]3(O)CC[C@H](C1)O)C
• InChI: InChI=1S/C19H27NO4/c1-20-9-8-18-11-13(21)6-7-19(18,22)15(20)10-12-4-5-14(23-2)17(24-3)16(12)18/h4-5,13,15,21-22H,6-11H2,1-3H3/t13-,15-,18-,19-/m1/s1
• InChIKey: LCAHPIFLPICNRW-SVYNMNNPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10S,13R)-3,4-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-triene-10,13-diol
• IUPAC Traditional name: drotebanol
• Synonyms: Drotebanol; Oxymethebanol; Drotebanol

Database IDs

• CAS Number: 3176-03-2
• PubChem SID: 162221516
• PubChem CID: 5463863
• Chemspider ID: 16736125
• KEGG ID: D01496
• Unique Ingredient Identifier: 7RS2Q8MCK8
• Wikipedia Title: Drotebanol

CALCULATED PROPERTIES

• Acid pKa: 13.643597
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.12219
• LogD (pH = 7.4): -0.48397934
• Log P: 1.0239459
• Molar Refractivity: 91.993 cm^3
• Polarizability: 36.04947 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 165-167 °C (329-332.6°F)

Pharmacology Properties

• Legal Status: Schedule I (US)