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

• ChemBase ID: 174951
• 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)CCN1CC1CC1)O)OC
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@]4(O)CCC1=O)CC1CC1
• InChI: InChI=1S/C21H25NO4/c1-25-15-5-4-13-10-16-21(24)7-6-14(23)19-20(21,17(13)18(15)26-19)8-9-22(16)11-12-2-3-12/h4-5,12,16,19,24H,2-3,6-11H2,1H3/t16-,19+,20+,21-/m1/s1
• InChIKey: DSMNGWOUQMYTJH-MBPVOVBZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-4-(cyclopropylmethyl)-17-hydroxy-10-methoxy-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-(cyclopropylmethyl)-17-hydroxy-10-methoxy-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: O3-Methyl-(-)-naltrexone; Naltrexone-3-methyl Ether; 3-Methoxynaltrexone; N-Cyclopropylmethylnoroxycodone; 3-O-Methylnaltrexone; 17-(Cyclopropylmethyl)-4,5α-epoxy-14-hydroxy-3-methoxy-morphinan-6-one; Naltrexone 3-Methyl Ether

Database IDs

• CAS Number: 16617-07-5
• PubChem SID: 164230861
• PubChem CID: 5487695

CALCULATED PROPERTIES

• Acid pKa: 13.562589
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.3415529
• LogD (pH = 7.4): 0.28866398
• Log P: 1.8154427
• Molar Refractivity: 95.9838 cm^3
• Polarizability: 37.80974 Å^3
• Polar Surface Area: 59.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - N285765

A potent antagonist of the antinociceptive effects of heroin.

REFERENCES

• Teppema, L., et al.: Anesthesiol., 109, 689 (2008)
• Cami-Kobeci, G., et al.: J. Med. Chem., 52, 1546 (2008)
• Nagase, H., et al.: Bioorg. Med. Chem. Lett., 20, 121 (2008)