(3S)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione; 2,3-dihydroxybutanedioic acid

• ChemBase ID: 160101
• Molecular Formular: C17H22N2O8
• Molecular Mass: 382.36518
• Monoisotopic Mass: 382.13761567
• SMILES: N1C(=O)CC[C@](C1=O)(c1ccc(cc1)N)CC.C(C(O)C(=O)O)(O)C(=O)O
• Canonical SMILES: OC(C(C(=O)O)O)C(=O)O.CC[C@]1(CCC(=O)NC1=O)c1ccc(cc1)N
• InChI: InChI=1S/C13H16N2O2.C4H6O6/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9;5-1(3(7)8)2(6)4(9)10/h3-6H,2,7-8,14H2,1H3,(H,15,16,17);1-2,5-6H,(H,7,8)(H,9,10)/t13-;/m0./s1
• InChIKey: DQUXPVVSVXIQNE-ZOWNYOTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione; 2,3-dihydroxybutanedioic acid
• IUPAC Traditional name: (.+-.)-tartaric acid; dl-aminoglutethimide
• Synonyms: R-(+)-3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione L-Tartrate Salt; d-Aminoglutethimide L-tartrate; R-(+)-Aminoglutethimide L-Tartrate Salt

Database IDs

• CAS Number: 57344-88-4
• PubChem SID: 162254236
• PubChem CID: 15179484

CALCULATED PROPERTIES

• Acid pKa: 11.691995
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.2744231
• LogD (pH = 7.4): 1.2991968
• Log P: 1.2995443
• Molar Refractivity: 65.3543 cm^3
• Polarizability: 24.911802 Å^3
• Polar Surface Area: 72.19 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Hexane
• Apperance: White Solid
• Melting Point: 149-150°C

DETAILS

Toronto Research Chemicals - A609815

An aromatase inhibitor. Also blocks adrenal steroidogenesis.

REFERENCES

• Santen, R.J. and Misbin, R.I.: Pharmacotherapy, 1, 95 (1981)
• Havlin, K.A. and Trump, D.L.: Cancer Threat. Res., 39, 83 (1988)