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

• ChemBase ID: 175658
• Molecular Formular: C34H44O11
• Molecular Mass: 628.70656
• Monoisotopic Mass: 628.28836223
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@@](CC1)(CC)[C@](CC2)(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#C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](O[C@@]2(C#C)CC[C@@H]3[C@]2(CC)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/C34H44O11/c1-7-33-15-13-24-23-12-10-22(38)17-21(23)9-11-25(24)26(33)14-16-34(33,8-2)45-32-30(43-20(5)37)28(42-19(4)36)27(41-18(3)35)29(44-32)31(39)40-6/h2,17,23-30,32H,7,9-16H2,1,3-6H3/t23-,24+,25+,26-,27-,28-,29-,30+,32-,33-,34-/m0/s1
• InChIKey: MZFAJGPABMFVLB-IHVSJPMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-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 (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]oxy}oxane-2-carboxylate
• Synonyms: D-(-)-Norgestrel Tri-O-acetyl β-D-Glucuronide Methyl Ester; 17-Ethynyl-18-methyl-19-nortestosterone Tri-O-acetyl Glucuronide Methyl Ester; Levonorgestrel Tri-O-acetyl Glucuronide Methyl Ester

Database IDs

• PubChem SID: 164231568
• PubChem CID: 71751216

CALCULATED PROPERTIES

• Acid pKa: 19.278172
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 3.6805058
• LogD (pH = 7.4): 3.6805058
• Log P: 3.6805058
• Molar Refractivity: 156.5298 cm^3
• Polarizability: 63.03788 Å^3
• Polar Surface Area: 140.73 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - N689535

An intermediate to the glucuronide metabolite of Levonorgestrel.