3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate

• ChemBase ID: 175710
• Molecular Formular: C16H19NO4
• Molecular Mass: 289.32636
• Monoisotopic Mass: 289.13140809
• SMILES: O(C(=O)[C@@H](c1ccccc1)CO)C1CC2C3C(C(N2)C1)O3
• Canonical SMILES: OC[C@H](c1ccccc1)C(=O)OC1CC2NC(C1)C1C2O1
• InChI: InChI=1S/C16H19NO4/c18-8-11(9-4-2-1-3-5-9)16(19)20-10-6-12-14-15(21-14)13(7-10)17-12/h1-5,10-15,17-18H,6-8H2/t10?,11-,12?,13?,14?,15?/m1/s1
• InChIKey: MOYZEMOPQDTDHA-AOAHJRJYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate
• IUPAC Traditional name: 3-oxa-9-azatricyclo[3.3.1.0^2,^4]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate
• Synonyms: 6β,7β-Epoxy-1αH,5αH-nortropan-3α-ol (-)-Tropate Ester; [7(S)-(1α,2β,4β,5α,7β)]-α-(Hydroxymethyl)-benzeneacetic Acid 3-Oxa-9-azatricyclo[3.3.1.02,4]non-7-yl Ester; Norhyoscine; Nor Scopolamine

Database IDs

• CAS Number: 4684-28-0
• PubChem SID: 164231620
• PubChem CID: 71751243

CALCULATED PROPERTIES

• Acid pKa: 15.1457405
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.4682107
• LogD (pH = 7.4): -0.9213078
• Log P: 0.51190436
• Molar Refractivity: 74.4266 cm^3
• Polarizability: 30.17853 Å^3
• Polar Surface Area: 71.09 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Diethyl Ether; Ethyl Acetate
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - N825880

Scopolamine (S200000) metabolite.

REFERENCES

• Wada, S. et al.; Xenobiotica 21, 1289 (1991)