(2R,3R,4R,5S,6R)-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}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 175615
• Molecular Formular: C26H34O8
• Molecular Mass: 474.54336
• Monoisotopic Mass: 474.22536805
• 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]1O)O)O)C(=O)O)C
• Canonical SMILES: C#C[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C26H34O8/c1-3-26(34-24-21(30)19(28)20(29)22(33-24)23(31)32)11-9-18-17-6-4-13-12-14(27)5-7-15(13)16(17)8-10-25(18,26)2/h1,12,15-22,24,28-30H,4-11H2,2H3,(H,31,32)/t15-,16+,17+,18-,19+,20+,21-,22+,24+,25-,26-/m0/s1
• InChIKey: CQOHDQNOAACQBL-LEUUCSQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-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}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-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}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (17α)-3-Οxo-19-norpregn-4-en-20-yn-17-yl β-D-Glucopyranosiduronic Acid; Norethindrone Glucuronide; Norethindrone β-D-Glucuronide

Database IDs

• CAS Number: 64701-11-7
• PubChem SID: 164231525
• PubChem CID: 71751192

CALCULATED PROPERTIES

• Acid pKa: 3.5531397
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.17386536
• LogD (pH = 7.4): -1.5921638
• Log P: 1.7666669
• Molar Refractivity: 119.7052 cm^3
• Polarizability: 47.578915 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White Solid
• Melting Point: 198-200°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - N676005

A metabolite of Norethindrone (N676000).

REFERENCES

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