(1S,5S,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene-6,14-dione

• ChemBase ID: 176025
• Molecular Formular: C19H19NO5
• Molecular Mass: 341.35786
• Monoisotopic Mass: 341.12632271
• SMILES: c12[C@]34[C@@]5([C@@H](C(=O)c1ccc(c2O[C@H]3C(=O)CC5)O)N(CC=C)CC4)O
• Canonical SMILES: C=CCN1CC[C@@]23[C@@]4([C@H]1C(=O)c1c3c(O[C@H]2C(=O)CC4)c(cc1)O)O
• InChI: InChI=1S/C19H19NO5/c1-2-8-20-9-7-18-13-10-3-4-11(21)15(13)25-17(18)12(22)5-6-19(18,24)16(20)14(10)23/h2-4,16-17,21,24H,1,5-9H2/t16-,17+,18+,19-/m1/s1
• InChIKey: IKMNPTIPIBFNPV-YDZRNGNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13R,17S)-10,17-dihydroxy-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-triene-6,14-dione
• IUPAC Traditional name: (1S,5S,13R,17S)-10,17-dihydroxy-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-triene-6,14-dione
• Synonyms: (5α)-4,5-Epoxy-3,14-dihydroxy-10-oxo-17-(2-propenyl)morphinan-6-one; 10-Keto Naloxone; 10-Oxo Naloxone

Database IDs

• PubChem SID: 164231935
• PubChem CID: 9905989

CALCULATED PROPERTIES

• Acid pKa: 8.060362
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.742262
• LogD (pH = 7.4): 0.901756
• Log P: 0.9914984
• Molar Refractivity: 89.3314 cm^3
• Polarizability: 34.700623 Å^3
• Polar Surface Area: 87.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O858150

A keto analog of the opioid antagonist Naloxone (N285000).