(1S,5R,13R,17R)-10-(acetyloxy)-14-oxo-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-17-yl acetate

• ChemBase ID: 174935
• Molecular Formular: C23H25NO6
• Molecular Mass: 411.4477
• Monoisotopic Mass: 411.16818753
• SMILES: c12[C@]34[C@]5([C@@H](Cc1ccc(c2O[C@H]3C(=O)CC5)OC(=O)C)N(CC4)CC=C)OC(=O)C
• Canonical SMILES: C=CCN1CC[C@@]23[C@]4([C@H]1Cc1c3c(O[C@H]2C(=O)CC4)c(cc1)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C23H25NO6/c1-4-10-24-11-9-22-19-15-5-6-17(28-13(2)25)20(19)29-21(22)16(27)7-8-23(22,18(24)12-15)30-14(3)26/h4-6,18,21H,1,7-12H2,2-3H3/t18-,21+,22+,23+/m1/s1
• InChIKey: HXBIBDFSLORHLJ-PVSGBFIBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17R)-10-(acetyloxy)-14-oxo-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-trien-17-yl acetate
• IUPAC Traditional name: (1S,5R,13R,17R)-10-(acetyloxy)-14-oxo-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-trien-17-yl acetate
• Synonyms: Naloxone-3,14-diacetate; (5α)-3,14-Bis(acetyloxy)-4,5-epoxy-17-(2-propenyl)morphinan-6-one, Diacetylnaloxone

Database IDs

• CAS Number: 50510-01-5
• PubChem SID: 164230845
• PubChem CID: 71750915

CALCULATED PROPERTIES

• Acid pKa: 16.370201
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.20262757
• LogD (pH = 7.4): 1.7313017
• Log P: 1.9721729
• Molar Refractivity: 107.0252 cm^3
• Polarizability: 42.299316 Å^3
• Polar Surface Area: 82.14 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White Solid