2-hydroxy-1-[(2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]ethan-1-one

• ChemBase ID: 159663
• Molecular Formular: C21H34O5
• Molecular Mass: 366.49166
• Monoisotopic Mass: 366.24062419
• SMILES: C1[C@H](C[C@H]2[C@](C1)(C1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)CO)O)C)C)O
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)C1[C@H]2CC[C@@H]2[C@]1(C)CC[C@H](C2)O
• InChI: InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18?,19-,20-,21-/m0/s1
• InChIKey: AODPIQQILQLWGS-ZLSPLEKWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-1-[(2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]ethan-1-one
• IUPAC Traditional name: 2-hydroxy-1-[(2S,5R,7S,10S,11S,14R,15S,17S)-5,14,17-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]ethanone
• Synonyms: allo-Tetrahydrocortisol; α-THF; Allo-3α-tetrahydro Cortisol; (3α,5α,11β)-3,11,17,21-Tetrahydroxypregnan-20-one; 3α,11β,17,21-Tetrahydroxy-5α-pregnan-20-one; 3α,5α-Tetrahydrocortisol; 5α-Pregnane-3α,11β,17α,21-tetraol-20-one; 5α-Tetrahydrocortisol; AL 3308; ATHF; Allotetrahydrocortisol; NSC 86469

Database IDs

• CAS Number: 302-91-0
• PubChem SID: 162253798
• PubChem CID: 50990134

CALCULATED PROPERTIES

• Acid pKa: 12.584778
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.1134999
• LogD (pH = 7.4): 1.1134971
• Log P: 1.1135
• Molar Refractivity: 97.6014 cm^3
• Polarizability: 39.0728 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 253-255°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A548500

A metabolite of Cortisol (H714615).

REFERENCES

• Quinkler, M., et al.: J. Clin. Endocrinol. Metab., 88, 2384 (2003)
• Draper, N., et al.: J. Endocrinol., 186, 251 (2003)
• Kotlowska, A., et al.: Clin. Biochem., 42, 448 (2003)