5-{7-chloro-2,4-dioxo-1H,2H,3H,4H,5H-chromeno[2,3-d]pyrimidin-5-yl}-1,3-diazinane-2,4,6-trione

• ChemBase ID: 153285
• Molecular Formular: C15H9ClN4O6
• Molecular Mass: 376.70816
• Monoisotopic Mass: 376.02106171
• SMILES: c1cc2c(cc1Cl)C(c1c(=O)[nH]c(=O)[nH]c1O2)C1C(=O)NC(=O)NC1=O
• Canonical SMILES: O=C1NC(=O)C(C(=O)N1)C1c2cc(Cl)ccc2Oc2c1c(=O)[nH]c(=O)[nH]2
• InChI: InChI=1S/C15H9ClN4O6/c16-4-1-2-6-5(3-4)7(8-10(21)17-14(24)18-11(8)22)9-12(23)19-15(25)20-13(9)26-6/h1-3,7-8H,(H2,19,20,23,25)(H2,17,18,21,22,24)
• InChIKey: GGEVZGGAQHNWQN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{7-chloro-2,4-dioxo-1H,2H,3H,4H,5H-chromeno[2,3-d]pyrimidin-5-yl}-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: 5-{7-chloro-2,4-dioxo-1H,3H,5H-chromeno[2,3-d]pyrimidin-5-yl}-1,3-diazinane-2,4,6-trione
• Synonyms: 5-(6-Chloro-2,4-dioxo-1,3,4,10-tetrahydro-2H-9-oxa-1,3-diaza-anthracen-10-yl)-pyrimidine-2,4,6-trione; EM20-25

Database IDs

• CAS Number: 141266-44-6
• MDL Number: MFCD00624842
• PubChem SID: 162247424
• PubChem CID: 4583626

CALCULATED PROPERTIES

• Acid pKa: 2.1083674
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.182592
• LogD (pH = 7.4): -2.2186618
• Log P: -0.10463589
• Molar Refractivity: 93.4013 cm^3
• Polarizability: 32.288235 Å^3
• Polar Surface Area: 142.7 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL at ~60 °C
• Apperance: light yellow to yellow powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H9ClN4O6

DETAILS

Sigma Aldrich - SML0183

Biochem/physiol Actions
EM20-25 is an analog of HA14-1 that antagonizes the effects of the anti-apoptotic protein BCL-2, and causes opening of the mitochondrial permeability transition pore. Unlike HA14-1, EM20-25 does not effect mitochondrial respiration.