(1S,5R,13S,17S)-4-[(1-2H)cyclopropyl(2H2)methyl]-14-methylidene-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene-10,17-diol

• ChemBase ID: 174924
• Molecular Formular: C21H25NO3
• Molecular Mass: 339.4281
• Monoisotopic Mass: 339.18344367
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(=C)CC4)O2)CCN1CC1CC1)O)O
• Canonical SMILES: C=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O
• InChI: InChI=1S/C21H25NO3/c1-12-6-7-21(24)16-10-14-4-5-15(23)18-17(14)20(21,19(12)25-18)8-9-22(16)11-13-2-3-13/h4-5,13,16,19,23-24H,1-3,6-11H2/t16-,19+,20+,21-/m1/s1
• InChIKey: WJBLNOPPDWQMCH-MBPVOVBZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13S,17S)-4-[(1-^2H)cyclopropyl(^2H₂)methyl]-14-methylidene-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-10,17-diol
• IUPAC Traditional name: (1S,5R,13S,17S)-4-[(1-^2H)cyclopropyl(^2H₂)methyl]-14-methylidene-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-10,17-diol
• Synonyms: (5α)-17-(Cyclopropylmethyl-d3)-4,5-epoxy-6-methylenemorphinan-3,14-diol; (-)-Nalmefene-d3; 6-Deoxo-6-methylenenaltrexone-d3; 6-Desoxy-6-methylenenaltrexone-d3; JF 1-d3; Nalmetrene-d3; ORF 11676-d3; Nalmefene-d3

Database IDs

• PubChem SID: 164230834
• PubChem CID: 71750904

CALCULATED PROPERTIES

• Acid pKa: 10.35208
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.0076869
• LogD (pH = 7.4): 0.067021266
• Log P: 1.9476479
• Molar Refractivity: 95.2095 cm^3
• Polarizability: 37.331768 Å^3
• Polar Surface Area: 52.93 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N284402

A structural labelled analog of Naltrexone (N285780) with opiate antagonist activity used in pharmaceutical treatment of alcoholism. Other pharmacological applications of this compound aim to reduce food cravings, drug abuse and pulmonary disease in affec

REFERENCES

• Brittain, H.G., et al.: Anal. Profiles Drug Subs. Excip., 24, 351 (1996)
• Anton, R., et al.: J. Clin. Psychopharmacol., 24, 421 (1996)
• Bart, G., et al.: Neuropsychopharmacol., 30, 2254 (1996)
• Wu, X., et al.: Chem. Pharmacol. Bull., 54, 977 (1996)