(1S,5S,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-triene-6,14-dione

• ChemBase ID: 176027
• Molecular Formular: C21H23NO5
• Molecular Mass: 369.41102
• Monoisotopic Mass: 369.15762284
• SMILES: c1(c2c3c(cc1)C(=O)[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=O)[C@]4(O)CCC1=O)CC1CC1
• InChI: InChI=1S/C21H23NO5/c1-26-14-5-4-12-15-17(14)27-19-13(23)6-7-21(25)18(16(12)24)22(10-11-2-3-11)9-8-20(15,19)21/h4-5,11,18-19,25H,2-3,6-10H2,1H3/t18-,19+,20+,21-/m1/s1
• InChIKey: MPULCDMBFAYJIX-IVAOSVALSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,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-triene-6,14-dione
• IUPAC Traditional name: (1S,5S,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-triene-6,14-dione
• Synonyms: 10-Oxo-3-O-methylnaltrexone; 10-Ketonaltrexone-3-methyl Ether; (5α)-17-(Cyclopropylmethyl)-4,5-epoxy-14-hydroxy-3-methoxy-morphinan-6,10-dione; 10-Oxo Naltrexone Methyl Ether

Database IDs

• CAS Number: 96445-13-5
• PubChem SID: 164231937
• PubChem CID: 11303169

CALCULATED PROPERTIES

• Acid pKa: 13.301368
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.17688915
• LogD (pH = 7.4): 1.138852
• Log P: 1.1867199
• Molar Refractivity: 96.593 cm^3
• Polarizability: 37.966232 Å^3
• Polar Surface Area: 76.07 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO
• Apperance: Yellow Solid
• Melting Point: 90-95°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - O858210

Naltrexone derivative, showing significantly less potency than pure Naltrexone.

REFERENCES

• Archer, S., et al.: J. Med. Chem., 28, 974 (1985)