(1S,2S,5R,7R,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl(4,4,6,6-2H4)tetracyclo[8.7.0.02,7.011,15]heptadecan-17-one

• ChemBase ID: 178330
• Molecular Formular: C21H32O5
• Molecular Mass: 364.47578
• Monoisotopic Mass: 364.22497412
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1=O)([C@](CC2)(C(=O)CO)O)C)C)O
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@H](C2)O
• InChI: InChI=1S/C21H32O5/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/h12-15,18,22-23,26H,3-11H2,1-2H3/t12-,13-,14+,15+,18-,19+,20+,21+/m1/s1
• InChIKey: SYGWGHVTLUBCEM-ZIZPXRJBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7R,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl(4,4,6,6-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-17-one
• IUPAC Traditional name: (1S,2S,5R,7R,10S,11S,14R,15S)-5,14-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl(4,4,6,6-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-17-one
• Synonyms: (3α,5β)-3,17,21-Trihydroxypregnane-11,20-dione-d4; 3α,17,21-Trihydroxy-5β-pregnan-11,20-dione-d4; 5β-Pregnan-3α,17α,21-triol-11,20-dione-d4; 5β-Tetrahydrocortisone-d4; Ba 2681-d4; NSC 76984-d4; THE-d4; Tetrahydro E-d4; Tetrahydrocompound E-d4; Urocortisone-d4; Tetrahydro Cortisone-d4

Database IDs

• PubChem SID: 164234240
• PubChem CID: 71752445

CALCULATED PROPERTIES

• Acid pKa: 12.576202
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.4990141
• LogD (pH = 7.4): 1.4990113
• Log P: 1.4990143
• Molar Refractivity: 96.6762 cm^3
• Polarizability: 38.530174 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T293377

Labelled Tetrahydrocortisone (T293375). A normal mammalian metabolite of Cortisone (C696500).

REFERENCES

• Schneider, et al.: J. Biol. Chem., 183, 365 (1950)
• Barkemeyer, et al.: Appl. Microbiol., 8, 237 (1950)