(3S,6S)-3-benzyl-6-(hydroxymethyl)piperazine-2,5-dione

• ChemBase ID: 131736
• Molecular Formular: C12H14N2O3
• Molecular Mass: 234.25116
• Monoisotopic Mass: 234.10044232
• SMILES: c1ccc(cc1)C[C@H]1C(=O)N[C@H](C(=O)N1)CO
• Canonical SMILES: OC[C@@H]1NC(=O)[C@@H](NC1=O)Cc1ccccc1
• InChI: InChI=1S/C12H14N2O3/c15-7-10-12(17)13-9(11(16)14-10)6-8-4-2-1-3-5-8/h1-5,9-10,15H,6-7H2,(H,13,17)(H,14,16)/t9-,10-/m0/s1
• InChIKey: WIJKWEYCUNYTGY-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S)-3-benzyl-6-(hydroxymethyl)piperazine-2,5-dione
• IUPAC Traditional name: (3S,6S)-3-benzyl-6-(hydroxymethyl)piperazine-2,5-dione
• Synonyms: Cyclo(Phe-Ser)

Database IDs

• CAS Number: 35591-00-5
• MDL Number: MFCD00056023
• PubChem SID: 24892499; 162226013
• PubChem CID: 6951076

CALCULATED PROPERTIES

• Acid pKa: 10.68975
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.4636241
• LogD (pH = 7.4): -0.463819
• Log P: -0.4636216
• Molar Refractivity: 60.7575 cm^3
• Polarizability: 23.719204 Å^3
• Polar Surface Area: 78.43 Å^2
• Rotatable Bonds: 3
• 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
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (TLC)

DETAILS

Sigma Aldrich - C2524

Biochem/physiol Actions
Intermediate in the biosynthesis of gliotoxin by Trichoderma viride.