(1S,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5,9-tetraen-14-one

• ChemBase ID: 1943
• Molecular Formular: C18H20O2
• Molecular Mass: 268.3502
• Monoisotopic Mass: 268.14632988
• SMILES: c1(cc2c(cc1)[C@@H]1C(=CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)O
• Canonical SMILES: Oc1ccc2c(c1)CC=C1[C@@H]2CC[C@]2([C@H]1CCC2=O)C
• InChI: InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3-5,10,14,16,19H,2,6-9H2,1H3/t14-,16+,18+/m1/s1
• InChIKey: WKRLQDKEXYKHJB-HFTRVMKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5,9-tetraen-14-one; (1S,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6,9-tetraen-14-one
• IUPAC Traditional name: equilin
• Synonyms: 1,3,5,7-Estratetraen-3-ol-17-one; 3-Hydroxyestra-1,3,5(10),7-tetraen-17-one; NSC 10971; Equilin; 1,3,5(10),7-Estratetraen-3-ol-17-one; 3-Hydroxy-1,3,5(10),7-estratetraen-17-one; 7-Dehydroestrone; Equilin; 1,3,5(10),7-雌甾四烯-3-醇-17-酮; 3-羟基-1,3,5(10),7-雌甾四烯-17-酮; 7-脱氢雌酮; 马烯雌甾酮

Database IDs

• CAS Number: 474-86-2
• EC Number: 207-488-6
• MDL Number: MFCD00046223
• Beilstein Number: 2624302
• PubChem SID: 46506633; 24869978; 24894666; 160965398
• PubChem CID: 223368

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.414163
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.9033968
• LogD (pH = 7.4): 3.8992908
• Log P: 3.9034495
• Molar Refractivity: 79.9324 cm^3
• Polarizability: 30.675314 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.8
• LOG S: -4.3
• Solubility (Water): 1.33e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.00141 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Chloroform; Dioxane; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 233-235°C; 238-240 °C(lit.)

Safety Information

• Storage Condition: Refrigerator
• RTECS: KG6650000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-40-62
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351-H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C18H20O2

DETAILS

DrugBank - DB02187

• Drug Groups: experimental
• Description: An estrogenic steroid produced by horses. It has a total of four double bonds in the A- and B-ring. High concentration of euilin is found in the urine of pregnant mares. [PubChem]
• External Links: Wikipedia

Sigma Aldrich - 46247

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - E592800

An estrogen found in Premarin, which is a mixture of conjugated estrogens widely used in hormone replacement therapy.

REFERENCES

• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2009)
• Okamoto, Y., et al.: Toxicol. Lett., 193, 224 (2009)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)
• Suri, R., et al.: Environ. Sci. Technol., 44, 1373 (2009)