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

• ChemBase ID: 133607
• Molecular Formular: C17H22N2O8
• Molecular Mass: 382.36518
• Monoisotopic Mass: 382.13761567
• SMILES: CC[C@@]1(CCC(=O)NC1=O)c1ccc(cc1)N.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
• Canonical SMILES: O[C@H]([C@H](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-;1-,2-/m11/s1
• InChIKey: DQUXPVVSVXIQNE-IMXLTCNTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid; (3R)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione
• IUPAC Traditional name: (R)-aminoglutethimide; L(+)-tartaric acid
• Synonyms: R-(+)-p-Aminoglutethimide (+)-tartrate salt

Database IDs

• CAS Number: 57344-88-4
• PubChem SID: 162227884; 24890514
• PubChem CID: 71308691

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

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

Sigma Aldrich - A123

Biochem/physiol Actions
Inhibitor of aromatases involved in conversion of androgens to estrogens, and thus useful in chemotherapy of hormone-sensitive tumors (e.g., breast cancer).1 Also inhibits corticosteroid biosynthesis, termed a "medical adrenalectomy."2