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

• ChemBase ID: 5404
• Molecular Formular: C19H28O2
• Molecular Mass: 288.42442
• Monoisotopic Mass: 288.20893014
• SMILES: C1CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@@H](CC2)O)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@H]2O)C)C
• InChI: InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17+,18-,19-/m0/s1
• InChIKey: MUMGGOZAMZWBJJ-KZYORJDKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one; (1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
• IUPAC Traditional name: epitestosterone
• Synonyms: (17α)-17-Ηydroxyandrost-4-en-3-one; 17-Epitestosterone; 17α-Testosterone; 17α-cis-Testosterone; 4-Androstene-17α-ol-3-one; NSC 26499; 17-epi-Testosterone; 17α-Hydroxy-4-androsten-3-one, 4-Androsten-17α-ol-3-one, cis-Testosterone, Isotestosterone; EPITESTOSTERONE; 17α-Hydroxy-4-androsten-3-one; 4-Androsten-17α-ol-3-one; cis-Testosterone; Isotestosterone; Epitestosterone; (10ALPHA,13ALPHA,14BETA,17ALPHA)-17-HYDROXYANDROST-4-EN-3-ONE

Database IDs

• CAS Number: 481-30-1
• MDL Number: MFCD00067129
• PubChem SID: 160968833; 24894346; 99444239
• PubChem CID: 10204

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.08686
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.3654232
• LogD (pH = 7.4): 3.3654232
• Log P: 3.3654232
• Molar Refractivity: 84.4298 cm^3
• Polarizability: 33.260063 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.99
• LOG S: -3.94
• Solubility (Water): 3.33e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 218-220°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: BV8395600
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 68
• Safety Statements: 22-36
• Personal Protective Equipment: Eyeshields, Gloves
• Drug Control: Home Office Schedule 4.2

Pharmacology Properties

• Gene Information: rat ... Ar(24208)

Product Information

• Empirical Formula (Hill Notation): C19H28O2

DETAILS

MP Biomedicals - 05213993

MP Biomedicals Rare Chemical collection

DrugBank - DB07768

Drug information: experimental

Sigma Aldrich - E5878

Biochem/physiol Actions
Epitestosterone is a naturally occurring steroid, an inactive epimer of testosterone.

Toronto Research Chemicals - T155005

Testosterone and epitestosterone are endogenous steroids that differ in the configuration of the hydroxyl-bearing carbon at C-17. Testosterone is the predominant male sex hormone, whereas the role of epitestosterone is largely unclear. In humans, both and

REFERENCES

• Wudy, S., et al.: Steroids, 66, 759 (2001)
• Kootstra, P., et al.: Anal. Chim. Acta., 586, 82 (2001)
• Sten, T., et al.: Drug Metab. Dispos., 37, 417 (2001)