(1S,5R,13R,14S,17S)-4-(cyclopropylmethyl)-14-(methylamino)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene-10,17-diol

• ChemBase ID: 165268
• Molecular Formular: C21H28N2O3
• Molecular Mass: 356.45862
• Monoisotopic Mass: 356.20999277
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H]([C@H](CC4)NC)O2)CCN1CC1CC1)O)O
• Canonical SMILES: CN[C@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O
• InChI: InChI=1S/C21H28N2O3/c1-22-14-6-7-21(25)16-10-13-4-5-15(24)18-17(13)20(21,19(14)26-18)8-9-23(16)11-12-2-3-12/h4-5,12,14,16,19,22,24-25H,2-3,6-11H2,1H3/t14-,16+,19-,20-,21+/m0/s1
• InChIKey: MDPFGNLTFZJSEZ-LAKPAKELSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17S)-4-(cyclopropylmethyl)-14-(methylamino)-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,13R,14S,17S)-4-(cyclopropylmethyl)-14-(methylamino)-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: Des-N-(3-furanyl-2-propenamide) Nalfurafine; (5α,6β)-17-(Cyclopropylmethyl)-4,5-epoxy-6-(methylamino)-morphinan-3,14-diol; 6-Dehydroxy-6-methylamine-6α-naltrexol; (5α,6α)-17-(Cyclopropylmethyl)-4,5-epoxy-6-(methylamino)-morphinan-3,14-diol

Database IDs

• CAS Number: 102869-99-8; 102919-85-7
• PubChem SID: 162259401
• PubChem CID: 15908858

CALCULATED PROPERTIES

• Acid pKa: 10.408209
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -5.013886
• LogD (pH = 7.4): -2.7897937
• Log P: 1.0131801
• Molar Refractivity: 98.831 cm^3
• Polarizability: 39.102043 Å^3
• Polar Surface Area: 64.96 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Ethyl Acetate; Methanol
• Apperance: Beige Solid; White Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C988740

Opioid receptor antagonist. Used in the preparation of opioid κ-agonist TRK-820 and other related compounds.

Toronto Research Chemicals - C988730

Opioid receptor antagonist.

REFERENCES

• Mohamed, M.S. et al.: J. Med. Chem. 29, 1551 (1986)
• Nagase, H. et al.: Chem. Pharm. Bull. 46, 366 (1998).
• Mohamed, M.S. et al.: J. Med. Chem. 29, 1551 (1986).