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

• ChemBase ID: 172085
• Molecular Formular: C21H25NO4
• Molecular Mass: 355.4275
• Monoisotopic Mass: 355.17835829
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(=O)CC4)O2)CCN1CC1CCC1)O)O
• Canonical SMILES: O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CCC2)ccc1O)O
• InChI: InChI=1S/C21H25NO4/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/h4-5,12,16,19,23,25H,1-3,6-11H2/t16-,19+,20+,21-/m1/s1
• InChIKey: VANAVLBJMFLURS-MBPVOVBZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-4-(cyclobutylmethyl)-10,17-dihydroxy-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,17S)-4-(cyclobutylmethyl)-10,17-dihydroxy-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)-17-(Cyclobutylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one; 17-(Cyclobutylmethyl)-4,5α-epoxy-3,14-dihydroxymorphinan-6-one; 6-Deoxy-6-oxonalbuphine; 6-Ketonalbuphine; EN 1655; N-(Cyclobutylmethyl)noroxymorphone; Nalbuphone; 6-Keto Nalbuphine

Database IDs

• CAS Number: 16676-33-8
• PubChem SID: 164227995
• PubChem CID: 44465003

CALCULATED PROPERTIES

• Acid pKa: 10.136171
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.1617802
• LogD (pH = 7.4): 0.34527996
• Log P: 1.7772841
• Molar Refractivity: 96.1025 cm^3
• Polarizability: 37.739212 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K195500

A metabolite of Nalbuphine (N232500).

REFERENCES

• Kotick, M.P., et al.: J. Med. Chem., 24, 1445 (1981)