(3S,8aS)-3-[(4-hydroxyphenyl)methyl]-octahydropyrrolo[1,2-a]piperazine-1,4-dione

• ChemBase ID: 4091
• Molecular Formular: C14H16N2O3
• Molecular Mass: 260.28844
• Monoisotopic Mass: 260.11609238
• SMILES: N1[C@H](C(=O)N2[C@H](C1=O)CCC2)Cc1ccc(cc1)O
• Canonical SMILES: O=C1N[C@@H](Cc2ccc(cc2)O)C(=O)N2[C@H]1CCC2
• InChI: InChI=1S/C14H16N2O3/c17-10-5-3-9(4-6-10)8-11-14(19)16-7-1-2-12(16)13(18)15-11/h3-6,11-12,17H,1-2,7-8H2,(H,15,18)/t11-,12-/m0/s1
• InChIKey: LSGOTAXPWMCUCK-RYUDHWBXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,8aS)-3-[(4-hydroxyphenyl)methyl]-octahydropyrrolo[1,2-a]piperazine-1,4-dione
• IUPAC Traditional name: (3S,8aS)-3-[(4-hydroxyphenyl)methyl]-hexahydropyrrolo[1,2-a]piperazine-1,4-dione
• Synonyms: Maculosin; Cyclo-(Pro-Tyr); (3s,8ar)-3-(4-Hydroxybenzyl)Hexahydropyrrolo[1,2-a]Pyrazine-1,4-Dione

Database IDs

• CAS Number: 4549-02-4
• MDL Number: MFCD03093467
• PubChem SID: 46507651; 160967524; 24893082
• PubChem CID: 119404

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.489837
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.55234456
• LogD (pH = 7.4): 0.5489038
• Log P: 0.5523886
• Molar Refractivity: 68.8838 cm^3
• Polarizability: 26.65249 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.44
• LOG S: -1.37
• Solubility (Water): 1.12e+01 g/l

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: >99% (TLC)
• Empirical Formula (Hill Notation): C14H16N2O3

DETAILS

DrugBank - DB04520

Drug information: experimental

Sigma Aldrich - C8607

Application
Phytotoxin that induces a high degree of phosphorylation of histones.