(1S,5R,13R,16S,17S)-4-(cyclopropylmethyl)-10,16,17-trihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one

• ChemBase ID: 170956
• Molecular Formular: C20H23NO5
• Molecular Mass: 357.40032
• Monoisotopic Mass: 357.15762284
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(=O)C[C@@H]4O)O2)CCN1CC1CC1)O)O
• Canonical SMILES: O=C1C[C@H](O)[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O
• InChI: InChI=1S/C20H23NO5/c22-12-4-3-11-7-14-20(25)15(24)8-13(23)18-19(20,16(11)17(12)26-18)5-6-21(14)9-10-1-2-10/h3-4,10,14-15,18,22,24-25H,1-2,5-9H2/t14-,15+,18+,19+,20+/m1/s1
• InChIKey: GEJUGVQZUBDPAB-KRUJCJHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,16S,17S)-4-(cyclopropylmethyl)-10,16,17-trihydroxy-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,16S,17S)-4-(cyclopropylmethyl)-10,16,17-trihydroxy-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: 8β-Hydroxy Naltrexone

Database IDs

• PubChem SID: 164226866
• PubChem CID: 71749201

CALCULATED PROPERTIES

• Acid pKa: 10.076394
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.1681013
• LogD (pH = 7.4): -0.42825112
• Log P: 0.57872957
• Molar Refractivity: 92.709 cm^3
• Polarizability: 36.550724 Å^3
• Polar Surface Area: 90.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Brown Solid
• Melting Point: 220-225°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H948540

A by-product of Naltrexone.