methyl (1S,5R,13R,16S,17S)-16,17-dihydroxy-10-methoxy-14-oxo-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene-4-carboxylate

• ChemBase ID: 166089
• Molecular Formular: C19H21NO7
• Molecular Mass: 375.37254
• Monoisotopic Mass: 375.13180202
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(=O)C[C@@H]4O)O2)CCN1C(=O)OC)O)OC
• Canonical SMILES: COC(=O)N1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2C(=O)C[C@@H]4O)c(cc1)OC)O
• InChI: InChI=1S/C19H21NO7/c1-25-11-4-3-9-7-12-19(24)13(22)8-10(21)16-18(19,14(9)15(11)27-16)5-6-20(12)17(23)26-2/h3-4,12-13,16,22,24H,5-8H2,1-2H3/t12-,13+,16+,18+,19+/m1/s1
• InChIKey: NXOJZPAMXKBXTA-RUXMKHLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,5R,13R,16S,17S)-16,17-dihydroxy-10-methoxy-14-oxo-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-4-carboxylate
• IUPAC Traditional name: methyl (1S,5R,13R,16S,17S)-16,17-dihydroxy-10-methoxy-14-oxo-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-4-carboxylate
• Synonyms: N-Des(cyclopropylmethyl)-N-methoxycarbonyl-3-O-methyl 8β-Hydroxy Naltrexone

Database IDs

• PubChem SID: 162260222
• PubChem CID: 71315556

CALCULATED PROPERTIES

• Acid pKa: 12.313509
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.03794535
• LogD (pH = 7.4): -0.037950575
• Log P: -0.03794528
• Molar Refractivity: 91.1441 cm^3
• Polarizability: 36.065132 Å^3
• Polar Surface Area: 105.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - D288615

Used in the preparation of Naltrexone by-product.