(1S,5R,13R,16S,17S)-10,16,17-trihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one

• ChemBase ID: 166093
• Molecular Formular: C16H17NO5
• Molecular Mass: 303.30988
• Monoisotopic Mass: 303.11067265
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(=O)C[C@@H]4O)O2)CCN1)O)O
• Canonical SMILES: O=C1C[C@H](O)[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2NCC3)ccc1O)O
• InChI: InChI=1S/C16H17NO5/c18-8-2-1-7-5-10-16(21)11(20)6-9(19)14-15(16,3-4-17-10)12(7)13(8)22-14/h1-2,10-11,14,17-18,20-21H,3-6H2/t10-,11+,14+,15+,16+/m1/s1
• InChIKey: OSKFABMIIYXDPB-DKDKVSGOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,16S,17S)-10,16,17-trihydroxy-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,13R,16S,17S)-10,16,17-trihydroxy-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: N-Des(cyclopropylmethyl) 8β-Hydroxy Naltrexone

Database IDs

• PubChem SID: 162260226
• PubChem CID: 71315560

CALCULATED PROPERTIES

• Acid pKa: 10.104156
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -3.472612
• LogD (pH = 7.4): -2.0377955
• Log P: -0.73197967
• Molar Refractivity: 75.4723 cm^3
• Polarizability: 29.941547 Å^3
• Polar Surface Area: 99.02 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Dimethylformamide; Methanol
• Apperance: Light Brown Solid

DETAILS

Toronto Research Chemicals - D288630

Used in the preparation of Naltrexone by-product.