methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl]oxy}oxane-2-carboxylate

• ChemBase ID: 175621
• Molecular Formular: C33H42O11
• Molecular Mass: 614.67998
• Monoisotopic Mass: 614.27271216
• SMILES: O=C1CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C#C)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)C
• Canonical SMILES: COC(=O)[C@H]1O[C@H](O[C@@]2(C#C)CC[C@@H]3[C@]2(C)CC[C@H]2[C@H]3CCC3=CC(=O)CC[C@H]23)[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C33H42O11/c1-7-33(15-13-25-24-10-8-20-16-21(37)9-11-22(20)23(24)12-14-32(25,33)5)44-31-29(42-19(4)36)27(41-18(3)35)26(40-17(2)34)28(43-31)30(38)39-6/h1,16,22-29,31H,8-15H2,2-6H3/t22-,23+,24+,25-,26+,27+,28+,29-,31+,32-,33-/m0/s1
• InChIKey: RFLHCSWBTWOZAI-WCNZIMLUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]oxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]oxy}oxane-2-carboxylate
• Synonyms: (17α)-3-Οxo-19-norpregn-4-en-20-yn-17-yl 2,3,4-Tri-O-acetyl-β-D-glucopyranosiduronic Acid Methyl Ester; Norethindrone 2,3,4-Tri-O-Acetyl-glucuronide Methyl Ester; Norethindrone 2,3,4-Tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• PubChem SID: 164231531
• PubChem CID: 71751196

CALCULATED PROPERTIES

• Acid pKa: 19.278296
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 3.235937
• LogD (pH = 7.4): 3.235937
• Log P: 3.235937
• Molar Refractivity: 151.9288 cm^3
• Polarizability: 61.209217 Å^3
• Polar Surface Area: 140.73 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N676040

A protected metabolite of Norethindrone (N676000).

REFERENCES

• Layne, D.S., et al.: Biochem. Pharmacol., 12, 905 (1963)