(1S,2S,5R,7R,10S,11S,14R,15S)-5,14-dihydroxy-14-[2-hydroxy(2H2)acetyl]-2,15-dimethyl(1,16,16-2H3)tetracyclo[8.7.0.02,7.011,15]heptadecan-17-one

• ChemBase ID: 136535
• Molecular Formular: C21H32O5
• Molecular Mass: 364.47578
• Monoisotopic Mass: 364.22497412
• SMILES: [C@H]12[C@@H](CC[C@H]3[C@@]1(CC[C@H](C3)O)C)[C@@H]1CC[C@@]([C@]1(CC2=O)C)(C(=O)CO)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-APMKBJTNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7R,10S,11S,14R,15S)-5,14-dihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,15-dimethyl(1,16,16-^2H₃)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-hydroxy(^2H₂)acetyl]-2,15-dimethyl(1,16,16-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-17-one
• Synonyms: Tetrahydrocortisone-d5; 5β-Pregnan-3α,17α,21-triol-11,20-dione-9,12,12,21,21-d5; (3α,5β)-3,17,21-Trihydroxypregnane-11,20-dione-d5; 3α,17,21-Trihydroxy-5β-pregnan-11,20-dione-d4; 5β-Pregnan-3α,17α,21-triol-11,20-dione-d5; 5β-Tetrahydrocortisone-d5; Ba 2681-d5; NSC 76984-d5; THE-d5; Tetrahydro E-d5; Tetrahydrocompound E-d5; Urocortisone-d5; Tetrahydro Cortisone-d5

Database IDs

• EC Number: 200-161-9
• MDL Number: MFCD08705069
• PubChem SID: 162230805
• PubChem CID: 71309898

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

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol
• Apperance: White Solid
• Mass Shift: M+5

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3

Product Information

• Isotopic Purity: 98 atom % D
• Mol. Weight: mol wt 369.41 by atom % calculation
• Empirical Formula (Hill Notation): C21D5H27O5

DETAILS

Sigma Aldrich - 695971

Packaging
This product may be available from bulk stock and can be packaged on demand. For information on pricing, availability and packaging, please contact Stable Isotopes Customer Service.

Toronto Research Chemicals - T293378

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)