(1S,5S,13S,16S,17R)-16-chloro-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,14-tetraen-10-ol

• ChemBase ID: 164467
• Molecular Formular: C17H18ClNO2
• Molecular Mass: 303.78332
• Monoisotopic Mass: 303.1026065
• SMILES: c1(c2c3c(cc1)C[C@H]1[C@H]4[C@@]3([C@H](C=C[C@@H]4Cl)O2)CCN1C)O
• Canonical SMILES: Cl[C@H]1C=C[C@H]2[C@]34[C@@H]1[C@H](Cc1c4c(O2)c(cc1)O)N(C)CC3
• InChI: InChI=1S/C17H18ClNO2/c1-19-7-6-17-13-5-3-10(18)15(17)11(19)8-9-2-4-12(20)16(21-13)14(9)17/h2-5,10-11,13,15,20H,6-8H2,1H3/t10-,11-,13-,15-,17+/m0/s1
• InChIKey: VSGXFWNZWWGPCT-SXCOJBNFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13S,16S,17R)-16-chloro-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,14-tetraen-10-ol
• IUPAC Traditional name: (1S,5S,13S,16S,17R)-16-chloro-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,14-tetraen-10-ol
• Synonyms: (5α,8β)-8-Chloro-6,7-didehydro-4,5-epoxy-17-methyl-morphinan-3-ol; β-Chloromorphide

Database IDs

• CAS Number: 60048-95-5
• PubChem SID: 162258602
• PubChem CID: 198403

CALCULATED PROPERTIES

• Acid pKa: 10.225239
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.7689037
• LogD (pH = 7.4): 0.8182871
• Log P: 2.1617951
• Molar Refractivity: 83.2286 cm^3
• Polarizability: 31.90313 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - C369595

Morphine (M652290) derivative. Possible irreversible binders to the narcotic receptor.

REFERENCES

• Yeh, H. et al.; J. Pharm. Sci. 65, 902 (1976)