(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-triene-5,6,14-triol

• ChemBase ID: 156057
• Molecular Formular: C18H24O3
• Molecular Mass: 288.38136
• Monoisotopic Mass: 288.17254463
• SMILES: C[C@]12CC[C@@H]3c4ccc(c(c4CC[C@H]3[C@@H]1CC[C@@H]2O)O)O
• Canonical SMILES: O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2O)O
• InChI: InChI=1S/C18H24O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,16,19-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1
• InChIKey: QOZFCKXEVSGWGS-ZHIYBZGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,6,14-triol
• IUPAC Traditional name: 4-hydroxyestradiol
• Synonyms: 1,3,5(10)-Estratriene-3,4,17β-triol; 4-Hydroxyestradiol; 4-Hydroxy-17β-estradiol; (17β)-Estra-1,3,5(10)-triene-3,4,17-triol; 4-Hydroxyestradiol

Database IDs

• CAS Number: 5976-61-4
• MDL Number: MFCD00063335
• PubChem SID: 24895648; 162250195
• PubChem CID: 5282360

CALCULATED PROPERTIES

• Acid pKa: 9.694773
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 3.4419084
• LogD (pH = 7.4): 3.439752
• Log P: 3.441936
• Molar Refractivity: 81.8856 cm^3
• Polarizability: 31.912842 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Light Brown Solid
• Melting Point: >210°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere
• RTECS: KG7676000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• 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
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... ESR1(2099)rat ... Ar(24208)

Product Information

• Empirical Formula (Hill Notation): C18H24O3

DETAILS

Sigma Aldrich - H4637

Biochem/physiol Actions
4-Hydroxyestradiol, an metabolite of estradiol, forms adducts with adenine (N3) and guanine (N7) by depurinating sites in DNA of cultured human breast epithelial cells. This effect may play an important role in malignant transformation of these cells.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H4637.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - H941895

A metabolite of Estradiol.

REFERENCES

• Bucala, R., et al.: J. Clin. Endocrinol. Metab., 60, 841 (1985)
• Telang, N., et al.: Anticancer Res., et al.: 11, 1021 (1985)
• Seeger, H., et al.: Med. Sci. Res., 26, 481 (1985)
• Bolton, J., et al.: Chem. Res. Toxicol., 13, 135 (1985)