(1S,5R,13S,17S)-4-(cyclopropylmethyl)-9-[(1S,13S,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-14-methylidene-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-9-yl]-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: 162369
• Molecular Formular: C42H48N2O6
• Molecular Mass: 676.84032
• Monoisotopic Mass: 676.35123727
• SMILES: c1(c2c3c(cc1c1c(c4c5c(c1)CC1[C@]6([C@@]5([C@H](C(=C)CC6)O4)CCN1CC1CC1)O)O)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(CC2N(CC3)CC2CC2)cc(c1O)c1cc2C[C@H]3N(CC[C@]45c2c(c1O)O[C@H]4C(=C)CC[C@@]35O)CC1CC1)O
• InChI: InChI=1S/C42H48N2O6/c1-21-7-9-41(47)29-17-25-15-27(33(45)35-31(25)39(41,37(21)49-35)11-13-43(29)19-23-3-4-23)28-16-26-18-30-42(48)10-8-22(2)38-40(42,32(26)36(50-38)34(28)46)12-14-44(30)20-24-5-6-24/h15-16,23-24,29-30,37-38,45-48H,1-14,17-20H2/t29?,30?,37-,38-,39-,40-,41+,42+/m0/s1
• InChIKey: DEKUTJDLMXTWRE-YXCFLIRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13S,17S)-4-(cyclopropylmethyl)-9-[(1S,13S,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-14-methylidene-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-9-yl]-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-(cyclopropylmethyl)-9-[(1S,13S,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-14-methylidene-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-9-yl]-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)-(5'α)-17,17'-Bis(cyclopropylmethyl)-4,5:4',5'-diepoxy-6,6'-bis(methylene)-[2,2'-bimorphinan]-3,3',14,14'-tetrol; 2,2'-Bis(6-deoxo-6-methylenenaltrexone); Nalmefene Impurity; 2,2'-Bisnalmefene (Nalmefene Impurity)

Database IDs

• CAS Number: 176220-84-1
• PubChem SID: 162256504
• PubChem CID: 46780837

CALCULATED PROPERTIES

• Acid pKa: 9.04821
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.3670528
• LogD (pH = 7.4): -0.34409443
• Log P: 3.1112757
• Molar Refractivity: 189.4972 cm^3
• Polarizability: 75.28673 Å^3
• Polar Surface Area: 105.86 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Light Yellow solid
• Melting Point: 266-268°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B504000

Degradation product of Nalmefene.

REFERENCES

• Brittain, H.G., et al.: J. Pham. Sci. Tech., 50, 35 (1996)
• Murthy, S., et al.: J. Pharm. Biomed. Anal., 15, 221 (1996)