(1S,5R,13R,17S)-4-(but-3-en-1-yl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one hydrochloride

• ChemBase ID: 163116
• Molecular Formular: C20H24ClNO4
• Molecular Mass: 377.86186
• Monoisotopic Mass: 377.13938593
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(=O)CC4)O2)CCN1CCC=C)O)O.Cl
• Canonical SMILES: C=CCCN1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2C(=O)CC4)c(cc1)O)O.Cl
• InChI: InChI=1S/C20H23NO4.ClH/c1-2-3-9-21-10-8-19-16-12-4-5-13(22)17(16)25-18(19)14(23)6-7-20(19,24)15(21)11-12;/h2,4-5,15,18,22,24H,1,3,6-11H2;1H/t15-,18+,19+,20-;/m1./s1
• InChIKey: UMLGCEOOYPDDJJ-ITLPAZOVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-4-(but-3-en-1-yl)-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-trien-14-one hydrochloride
• IUPAC Traditional name: (1S,5R,13R,17S)-4-(but-3-en-1-yl)-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-trien-14-one hydrochloride
• Synonyms: (5α)-17-(3-Butenyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride; NIH 10458; N-(3-Butenyl) Noroxymorphone Hydrochloride

Database IDs

• CAS Number: 131670-05-8
• PubChem SID: 162257251
• PubChem CID: 71314313

CALCULATED PROPERTIES

• Acid pKa: 10.098057
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.1992264
• LogD (pH = 7.4): 0.46281904
• Log P: 1.6424692
• Molar Refractivity: 93.4772 cm^3
• Polarizability: 36.38 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B689940

An impurity of Naltrexone (N285750) with opioid activity.

REFERENCES

• Woods, J. et al.: NIDA Res. Monogr., 90, 421 (1988)