(1S,5S,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene-6,14-dione

• ChemBase ID: 176026
• Molecular Formular: C20H21NO5
• Molecular Mass: 355.38444
• Monoisotopic Mass: 355.14197278
• SMILES: c1(c2c3c(cc1)C(=O)[C@@H]1[C@]4([C@@]3([C@H](C(=O)CC4)O2)CCN1CC1CC1)O)O
• Canonical SMILES: O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C(=O)[C@H]2N(CC3)CC2CC2)ccc1O)O
• InChI: InChI=1S/C20H21NO5/c22-12-4-3-11-14-16(12)26-18-13(23)5-6-20(25)17(15(11)24)21(9-10-1-2-10)8-7-19(14,18)20/h3-4,10,17-18,22,25H,1-2,5-9H2/t17-,18+,19+,20-/m1/s1
• InChIKey: MLHMRULRADVYER-FUMNGEBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-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)-10,17-dihydroxy-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: (5α)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6,10-dione; 10-Ketonaltrexone; 10-Oxo Naltrexone

Database IDs

• CAS Number: 96445-14-6
• PubChem SID: 164231936
• PubChem CID: 5486980

CALCULATED PROPERTIES

• Acid pKa: 8.074142
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.02259397
• LogD (pH = 7.4): 0.9045845
• Log P: 0.8893295
• Molar Refractivity: 92.1107 cm^3
• Polarizability: 36.063473 Å^3
• Polar Surface Area: 87.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 160-165°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - O858200

Naltrexone derivative. It is less potent than Naltrexone (N285750) and Oxymorphone (O876800).

REFERENCES

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