(1S,2R,10S,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 138841
• Molecular Formular: C21H32O2
• Molecular Mass: 316.47758
• Monoisotopic Mass: 316.24023026
• SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C)O
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](O)C)C)C
• InChI: InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16-,17+,18-,19-,20-,21+/m0/s1
• InChIKey: RWBRUCCWZPSBFC-RXRZZTMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: dihydroprogesterone
• Synonyms: 20α-Hydroxy-4-pregnen-3-one; 20α-Hydroxyprogesterone; 4-Pregnen-20α-ol-3-one; 20(S)-Hydroxyprogesterone; 20-Hydroxypregn-4-en-3-one; 20α-Dihydroprogesterone; 20α-Hydroxy-Δ4-pregnen-3-one; 20α-Hydroxydihydroprogesterone; 20α-Hydroxypregn-4-en-3-one; 20α-Progerol; 4-Pregnen-3-one-20α-ol; NSC 68630; Pregn-4-en-20α-ol-3-one; Pregn-4-ene-20α-ol-3-one; Progesterol-20α; Δ4-Pregnene-20α-ol-3-one; Δ4-Pregnen-20α-ol-3-one; 20α-羟基-4-孕烯-3-酮; 20α-羟基黄体酮; 4-孕烯-20α-醇-3-酮

Database IDs

• CAS Number: 145-14-2
• EC Number: 205-649-5
• MDL Number: MFCD00009823
• PubChem SID: 162233092
• PubChem CID: 8956

CALCULATED PROPERTIES

• Acid pKa: 19.003403
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.9411035
• LogD (pH = 7.4): 3.9411037
• Log P: 3.9411037
• Molar Refractivity: 93.7334 cm^3
• Polarizability: 36.94731 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: TU5559900
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C21H32O2

DETAILS

Toronto Research Chemicals - P712215

Δ4-Pregnen-20α-ol-3-one is the main metabolite of Progesterone (P755900). Studies shows regulation of estrogen receptor levels in breast cancer by Δ4-Pregnen-20α-ol-3-one and other progesterone metabolites.

REFERENCES

• Zhang, L. et al.: Yaoz. Xueb., 39, 613 (2004)
• Pawlak, K.J. et al.: J. Steroid. Biochem. Mol. Biol., 107, 172 (2004)