(1S,5R,13R,17S)-4-(cyclopropylmethyl)-6,17-dihydroxy-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: 170955
• Molecular Formular: C21H25NO5
• Molecular Mass: 371.4269
• Monoisotopic Mass: 371.17327291
• SMILES: c1(c2c3c(cc1)C([C@@H]1[C@]4([C@@]3([C@H](C(=O)CC4)O2)CCN1CC1CC1)O)O)OC
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2O)[C@]4(O)CCC1=O)CC1CC1
• InChI: InChI=1S/C21H25NO5/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/h4-5,11,16,18-19,24-25H,2-3,6-10H2,1H3/t16?,18-,19+,20+,21-/m1/s1
• InChIKey: JAERZOFTLPSTBG-NDSPWTRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-4-(cyclopropylmethyl)-6,17-dihydroxy-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)-6,17-dihydroxy-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: 10-Hydroxynaltrexone-3-methyl Ether; (5α)-17-(Cyclopropylmethyl)-4,5-epoxy-10,14-dihydroxy-3-methoxy-morphinan-6-one; 10-Hydroxy Naltrexone Methyl Ether

Database IDs

• PubChem SID: 164226865
• PubChem CID: 71749200

CALCULATED PROPERTIES

• Acid pKa: 13.253329
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.8715269
• LogD (pH = 7.4): 0.6562633
• Log P: 0.8964465
• Molar Refractivity: 97.1913 cm^3
• Polarizability: 38.524048 Å^3
• Polar Surface Area: 79.23 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; DMSO
• Apperance: Pale Brown Solid

DETAILS

Toronto Research Chemicals - H948535

Naltrexone derivative.

REFERENCES

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