(1S,2S,5R,7R,10R,11S,14R,15S)-14-[1-hydroxy(2H4)ethyl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecane-5,14-diol

• ChemBase ID: 176895
• Molecular Formular: C21H36O3
• Molecular Mass: 336.50874
• Monoisotopic Mass: 336.26644501
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(C(O)C)O)C)C)O
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(O)C(O)C)C)C
• InChI: InChI=1S/C21H36O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h13-18,22-24H,4-12H2,1-3H3/t13?,14-,15-,16-,17+,18+,19+,20+,21+/m1/s1
• InChIKey: SCPADBBISMMJAW-HWPIAJDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7R,10R,11S,14R,15S)-14-[1-hydroxy(^2H₄)ethyl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-diol
• IUPAC Traditional name: (1S,2S,5R,7R,10R,11S,14R,15S)-14-[1-hydroxy(^2H₄)ethyl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-diol
• Synonyms: (3α,5β,20S)-Pregnane-3,17,20-triol-d4; 5β-Pregnane-3α,17,20α-triol-d4; 3α,17α,20α-Trihydroxy-5β-pregnane; 5β-Pregnane-3α,17α,20α-triol-d4; NSC 52760-d4; Pregnanetriol-d4

Database IDs

• PubChem SID: 164232805
• PubChem CID: 71751756

CALCULATED PROPERTIES

• Acid pKa: 13.417381
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 2.8539984
• LogD (pH = 7.4): 2.8539982
• Log P: 2.8539987
• Molar Refractivity: 95.2319 cm^3
• Polarizability: 38.348473 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P705162

Labelled Pregnanetriol, a steroid present at elevated levels in the urine of patients with congenital adrenal hyperplasma. During treatment with cortisol replacement, elevated urine Pregnanetriol levels indicate insufficient dosage of cortisol. Pregnanetr

REFERENCES

• Kinoshita, K. et al.: J. Clin. Endocrinol., 26, 1219 (1966)
• Kotlowska, A. et al.: Clin. Biochem., 42, 448 (1966)
• Wang, J. et al.: Zhipu Xue., 25, 201 (1966)