methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-14,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-10-yl]oxy}oxane-2-carboxylate

• ChemBase ID: 174946
• Molecular Formular: C33H41NO13
• Molecular Mass: 659.67754
• Monoisotopic Mass: 659.25779038
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H]([C@@H](CC4)O)O2)CCN1CC1CC1)O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc3c4c2O[C@@H]2[C@@]54CCN([C@H](C3)[C@]5(O)CC[C@H]2O)CC2CC2)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C33H41NO13/c1-15(35)42-25-26(43-16(2)36)28(44-17(3)37)31(47-27(25)30(39)41-4)45-21-8-7-19-13-22-33(40)10-9-20(38)29-32(33,23(19)24(21)46-29)11-12-34(22)14-18-5-6-18/h7-8,18,20,22,25-29,31,38,40H,5-6,9-14H2,1-4H3/t20-,22-,25+,26+,27+,28-,29+,31-,32+,33-/m1/s1
• InChIKey: KQDCAOOISMGCLO-OWIJTNONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-14,17-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-10-yl]oxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(1S,5R,13R,14R,17S)-4-(cyclopropylmethyl)-14,17-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-10-yl]oxy}oxane-2-carboxylate
• Synonyms: (5α,6β)-17-(Cyclopropylmethyl)-4,5-epoxy-6,14-dihydroxy-morphinan-3-yl 3-(2’,3’,4’-Tri-O-acetyl)-β-D-glucuronide Methyl Ester; 6β-Naltrexol 3-(2',3',4'-Tri-O-acetyl)-β-D-glucuronide Methyl Ester

Database IDs

• PubChem SID: 164230856
• PubChem CID: 71750922

CALCULATED PROPERTIES

• Acid pKa: 13.476466
• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): -2.6259055
• LogD (pH = 7.4): -1.4102522
• Log P: 0.77968687
• Molar Refractivity: 156.6343 cm^3
• Polarizability: 63.66439 Å^3
• Polar Surface Area: 176.59 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - N285715

Protected 6β-Naltrexol 3-O-β-D-Glucuronide (N285710). A metabolite of 6β-Naltrexol (N285700). Narcotic antagonist.

REFERENCES

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