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

• ChemBase ID: 129097
• Molecular Formular: C21H36O3
• Molecular Mass: 336.50874
• Monoisotopic Mass: 336.26644501
• SMILES: O[C@H]1C[C@@H]2[C@]([C@@H]3[C@H]([C@H]4[C@](C)(CC3)[C@@](O)([C@@H](O)C)CC4)CC2)(C)CC1
• 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@@H](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-/m0/s1
• InChIKey: SCPADBBISMMJAW-UHHUKTEYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5R,7R,10R,11S,14R,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane-5,14-diol
• IUPAC Traditional name: pregnanetriol
• Synonyms: 5β-Pregnane-3α,17α,20α-triol; Pregnanetriol; (3α,5β,20S)-Pregnane-3,17,20-triol; 5β-Pregnane-3α,17,20α-triol; NSC 52760; 3α,17α,20α-Trihydroxy-5β-pregnane; Pregnanetriol; 5β-Pregnane-3α,17α,20α-triol; 3α,17α,20α-三羟基-5β-孕烷; 孕三醇; 5β-孕烷-3α,17α,20α-三醇

Database IDs

• CAS Number: 1098-45-9
• EC Number: 214-148-0
• MDL Number: MFCD00003678
• Beilstein Number: 2619975
• PubChem SID: 24898959; 162223396
• PubChem CID: 101967
• Chemspider ID: 92121
• Wikipedia Title: Pregnanetriol

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

PROPERTIES

Physical Property

• Solubility: chloroform/methanol (9:1): soluble50 mg/mL, clear, colorless

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (TLC); 98%
• Empirical Formula (Hill Notation): C21H36O3

DETAILS

Sigma Aldrich - 81575

Other Notes
Reference substance for the identification of pregnanetriol in body fluids1

Toronto Research Chemicals - P705160

Pregnanetriol is 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. Pregnanetriol is

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)