(1S,5R,6S,13R,17S)-6,10,17-trihydroxy-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-14-one

• ChemBase ID: 170978
• Molecular Formular: C19H21NO5
• Molecular Mass: 343.37374
• Monoisotopic Mass: 343.14197278
• SMILES: c12[C@]34[C@@]5([C@@H]([C@H](c1ccc(c2O[C@H]3C(=O)CC5)O)O)N(CC=C)CC4)O
• Canonical SMILES: C=CCN1CC[C@@]23[C@@]4([C@H]1[C@@H](O)c1c3c(O[C@H]2C(=O)CC4)c(cc1)O)O
• InChI: InChI=1S/C19H21NO5/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/h2-4,14,16-17,21,23-24H,1,5-9H2/t14-,16+,17-,18-,19+/m0/s1
• InChIKey: INQPEYLRYLSPCY-YCVVXREPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,6S,13R,17S)-6,10,17-trihydroxy-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-14-one
• IUPAC Traditional name: (1S,5R,6S,13R,17S)-6,10,17-trihydroxy-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-14-one
• Synonyms: (5α)-4,5-Epoxy-3,10α,14-trihydroxy-17-(2-propenyl)morphinan-6-one; 10α-Hydroxy Naloxone

Database IDs

• PubChem SID: 164226888
• PubChem CID: 71749209

CALCULATED PROPERTIES

• Acid pKa: 9.746083
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.63011515
• LogD (pH = 7.4): 0.5992566
• Log P: 0.70122504
• Molar Refractivity: 89.9297 cm^3
• Polarizability: 35.258068 Å^3
• Polar Surface Area: 90.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H948660

10α-Hydroxy Naloxone is a hydroxylated analog of the opioid antagonist Naloxone (N285000).