(11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2,4,6,8-pentaen-14-one

• ChemBase ID: 3187
• Molecular Formular: C18H18O2
• Molecular Mass: 266.33432
• Monoisotopic Mass: 266.13067982
• SMILES: c1(cc2c(cc1)c1c(cc2)[C@H]2[C@](CC1)(C(=O)CC2)C)O
• Canonical SMILES: Oc1ccc2c(c1)ccc1c2CC[C@]2([C@H]1CCC2=O)C
• InChI: InChI=1S/C18H18O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16,19H,6-9H2,1H3/t16-,18-/m0/s1
• InChIKey: PDRGHUMCVRDZLQ-WMZOPIPTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2,4,6,8-pentaen-14-one; (11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1(10),2,4,6,8-pentaen-14-one
• IUPAC Traditional name: equilenin
• Synonyms: Equilenin; 3-Hydroxyestra-1,3,5,7,9-pentaen-17-one; (+)-Equilenin; 3-Hydroxyestra-1,3,5(10),6,8-pentaen-17-one; E 400; Equilenine; NSC 9901; d-Equilenin; 3-Hydroxy-1,3,5(10),6,8-estrapentaen-17-one; Equilenin solution; 3-羟基-1,3,5(10),6,8-雌甾五烯-17-酮; 马萘雌甾酮 溶液

Database IDs

• CAS Number: 517-09-9
• EC Number: 200-835-2
• MDL Number: MFCD00003619
• PubChem SID: 160966631; 24860441; 46509080
• PubChem CID: 444865

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.778881
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.2990336
• LogD (pH = 7.4): 4.2972555
• Log P: 4.299056
• Molar Refractivity: 79.0356 cm^3
• Polarizability: 31.821459 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.32
• LOG S: -4.71
• Solubility (Water): 5.20e-03 g/l

PROPERTIES

Physical Property

• Flash Point: 2 °C; 35.6 °F

Safety Information

• European Hazard Symbols: Flammable (F); Harmful (Xn)
• UN Number: 1648
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-20/21/22-36
• Safety Statements: 16-36/37
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H312-H319-H332
• GHS Precautionary statements: P210-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1648 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Concentration: 100 ng/μL in acetonitrile
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C18H18O2

DETAILS

DrugBank - DB03515

• Drug Groups: experimental
• Description: An estrogenic steroid produced by HORSES. It has a total of five double bonds in the A- and B-ring. High concentration of equilenin is found in the URINE of pregnant mares. [PubChem]

Sigma Aldrich - 33693

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

Toronto Research Chemicals - E592400

Estrogenic steroidal hormone isolated from urine of pregnant mares. Occurs naturally in the d-form. Not found in human urine. Component of conjugated estrogenic hormones. Estrogen.

REFERENCES

• Corbellini et al.: Farmaco Ed. Sci., 19, 913 (1964)
• Stein, et al.: Tetrahedron, 26, 1917 (1964)