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

• ChemBase ID: 174942
• Molecular Formular: C20H25NO4
• Molecular Mass: 343.4168
• Monoisotopic Mass: 343.17835829
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H]([C@@H](CC4)O)O2)CCN1CC1CC1)O)O
• Canonical SMILES: O[C@@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CC2)ccc1O)O
• InChI: InChI=1S/C20H25NO4/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11/h3-4,11,14-15,18,22-24H,1-2,5-10H2/t14-,15-,18+,19+,20-/m1/s1
• InChIKey: JLVNEHKORQFVQJ-PYIJOLGTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-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-10,14,17-triol
• IUPAC Traditional name: (1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-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-10,14,17-triol
• Synonyms: 17-(Cyclopropylmethyl)-4,5-epoxy-(5α,6β)-morphinan-3,6,14-triol; 6β-Hydroxynaltrexone; β-Naltrexol; 6β-Naltrexol

Database IDs

• CAS Number: 49625-89-0
• PubChem SID: 164230852
• PubChem CID: 5486554

CALCULATED PROPERTIES

• Acid pKa: 10.297444
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.1513104
• LogD (pH = 7.4): -0.9519057
• Log P: 0.8429298
• Molar Refractivity: 92.3989 cm^3
• Polarizability: 36.369213 Å^3
• Polar Surface Area: 73.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White to Pale-Yellow Solid
• Melting Point: 90-96°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - N285700

A metabolite of Naltrexone. Narcotic antagonist.

REFERENCES

• Portoghese, P., et al,: J. Med. Chem., 37, 579 (1994)
• Ohkawa, S., et al.: J. Med. Chem., 41, 4177 (1998).