2-({3-[(2S)-2-amino-2-carboxyethyl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl}methyl)benzoic acid

• ChemBase ID: 154639
• Molecular Formular: C15H15N3O6
• Molecular Mass: 333.2961
• Monoisotopic Mass: 333.09608522
• SMILES: c1ccc(c(c1)Cn1c(=O)ccn(c1=O)C[C@@H](C(=O)O)N)C(=O)O
• Canonical SMILES: N[C@H](C(=O)O)Cn1ccc(=O)n(c1=O)Cc1ccccc1C(=O)O
• InChI: InChI=1S/C15H15N3O6/c16-11(14(22)23)8-17-6-5-12(19)18(15(17)24)7-9-3-1-2-4-10(9)13(20)21/h1-6,11H,7-8,16H2,(H,20,21)(H,22,23)/t11-/m0/s1
• InChIKey: UUIYULWYHDSXHL-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({3-[(2S)-2-amino-2-carboxyethyl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-1-yl}methyl)benzoic acid
• IUPAC Traditional name: 2-({3-[(2S)-2-amino-2-carboxyethyl]-2,6-dioxopyrimidin-1-yl}methyl)benzoic acid
• Synonyms: (αS)-α-amino-3-[(2-carboxyphenyl)methyl]-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinepropanoic acid; UBP302

Database IDs

• CAS Number: 745055-91-8
• MDL Number: MFCD06411607
• PubChem SID: 162248777
• PubChem CID: 6420161

CALCULATED PROPERTIES

• Acid pKa: 1.5674251
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -4.0983276
• LogD (pH = 7.4): -5.6901836
• Log P: -2.469564
• Molar Refractivity: 81.4112 cm^3
• Polarizability: 31.04348 Å^3
• Polar Surface Area: 141.24 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL at 60 °C (with warming for 5 minutes)
• Apperance: white to off-white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H15N3O6

DETAILS

Sigma Aldrich - U4135

Biochem/physiol Actions
UBP302 is a selective GluR5 antagonist. UBP302 is the active enantiomer of UB296 and is one of the most potent GluR5 antagonists available for research use.