(1S,5R,13R,14R,17S)-4-(cyclobutylmethyl)-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: 174914
• Molecular Formular: C21H28ClNO4
• Molecular Mass: 393.90432
• Monoisotopic Mass: 393.17068606
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H]([C@@H](CC4)O)O2)CCN1CC1CCC1)O)O.Cl
• Canonical SMILES: O[C@@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CCC2)ccc1O)O.Cl
• InChI: InChI=1S/C21H27NO4.ClH/c23-14-5-4-13-10-16-21(25)7-6-15(24)19-20(21,17(13)18(14)26-19)8-9-22(16)11-12-2-1-3-12;/h4-5,12,15-16,19,23-25H,1-3,6-11H2;1H/t15-,16-,19+,20+,21-;/m1./s1
• InChIKey: YZLZPSJXMWGIFH-IXDUCOGUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14R,17S)-4-(cyclobutylmethyl)-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-(cyclobutylmethyl)-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)-17-(Cyclobutylmethyl)-4,5-epoxy-morphinan-3,6,14-triol Hydrochloride; 6β-Nalbuphine Hydrochloride

Database IDs

• CAS Number: 60018-68-0
• PubChem SID: 164230824
• PubChem CID: 71750896

CALCULATED PROPERTIES

• Acid pKa: 10.392419
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.743254
• LogD (pH = 7.4): -0.7291438
• Log P: 1.1929245
• Molar Refractivity: 96.9999 cm^3
• Polarizability: 38.206367 Å^3
• Polar Surface Area: 73.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N232505

6β-Nalbuphine is an analog of Nalbuphine (N232500).

REFERENCES

• Yeh, S., et al.: J. Pharm. Sci., 50, 35 (1961)
• Yoo, Y., et al.: J. Anal. Toxicol., 19, 120, (1961)
• Wetzelsberger, N., et al.: Arzneim-Forsch., 38, 1768 (1961)