(1S,5R,13R,14R,17S)-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-10,14,17-triol hydrochloride

• ChemBase ID: 174929
• Molecular Formular: C19H24ClNO4
• Molecular Mass: 365.85116
• Monoisotopic Mass: 365.13938593
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H]([C@@H](CC4)O)O2)CCN1CC=C)O)O.Cl
• Canonical SMILES: C=CCN1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2[C@@H](CC4)O)c(cc1)O)O.Cl
• InChI: InChI=1S/C19H23NO4.ClH/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11;/h2-4,13-14,17,21-23H,1,5-10H2;1H/t13-,14-,17+,18+,19-;/m1./s1
• InChIKey: VFEZXRHXAKHILC-NHJKEJMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14R,17S)-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-10,14,17-triol hydrochloride
• IUPAC Traditional name: (1S,5R,13R,14R,17S)-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-10,14,17-triol hydrochloride
• Synonyms: (5α,6β)-4,5-Epoxy-17-(2-propenyl)morphinan-3,6,14-triol Hydrochloride; 6β-Naloxol Hydrochloride

Database IDs

• CAS Number: 55488-85-2
• PubChem SID: 164230839
• PubChem CID: 71750910

CALCULATED PROPERTIES

• Acid pKa: 10.144141
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.711431
• LogD (pH = 7.4): 0.02817055
• Log P: 1.0421176
• Molar Refractivity: 89.6196 cm^3
• Polarizability: 35.009438 Å^3
• Polar Surface Area: 73.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N284505

A metabolite of Naloxone (N285000). Naltrexone analog and Naloxone analog neutral μ-opioid antagonists and use thereof in treating drug abuse and pain.

REFERENCES

• Chatterjie, N., et al.: J. Med. Chem., 18, 490 (1975)
• Bilsky, E., et al.: J. Pharmacol. Exp. Ther., 277, 484 (1975)
• Blokhina, E., et al.: Eur. J, Pharmacol., 406, 227 (1975)