N-[3-(2,3-dihydroxybenzamido)phenyl]-2,3-dihydroxybenzamide

• ChemBase ID: 154864
• Molecular Formular: C20H16N2O6
• Molecular Mass: 380.35084
• Monoisotopic Mass: 380.10083624
• SMILES: c1cc(cc(c1)NC(=O)c1cccc(c1O)O)NC(=O)c1cccc(c1O)O
• Canonical SMILES: O=C(c1cccc(c1O)O)Nc1cccc(c1)NC(=O)c1cccc(c1O)O
• InChI: InChI=1S/C20H16N2O6/c23-15-8-2-6-13(17(15)25)19(27)21-11-4-1-5-12(10-11)22-20(28)14-7-3-9-16(24)18(14)26/h1-10,23-26H,(H,21,27)(H,22,28)
• InChIKey: MIQUEZGHEJGPJB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[3-(2,3-dihydroxybenzamido)phenyl]-2,3-dihydroxybenzamide
• IUPAC Traditional name: N-[3-(2,3-dihydroxybenzamido)phenyl]-2,3-dihydroxybenzamide
• Synonyms: N,N′-1,3-Phenylenebis-[2,3-dihydroxy-benzamide]; MST-312

Database IDs

• CAS Number: 368449-04-1
• PubChem SID: 162249002
• PubChem CID: 10385095

CALCULATED PROPERTIES

• Acid pKa: 7.7810993
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): 2.9405022
• LogD (pH = 7.4): 2.780141
• Log P: 2.942754
• Molar Refractivity: 105.0486 cm^3
• Polarizability: 38.018444 Å^3
• Polar Surface Area: 139.12 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: off-white to light tan powder

Safety Information

• European Hazard Symbols: Nature polluting (N)
• German water hazard class: 2
• Risk Statements: 50
• Safety Statements: 61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H400
• GHS Precautionary statements: P273
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H16N2O6

DETAILS

Sigma Aldrich - M3949

Biochem/physiol Actions
MST-312 is a telomerase Inhibitor. Telomeres are nucleoprotein complexes present on the ends of chromosomes, containing DNA segment tandem repeats that shorten with each repetitive cell cycle. Telomere shortening leads to loss of function, resulting in cell senescence and limited survivability. The reverse transcriptase, telomerase, maintains telomere length and function in immortalized cell lines and most cancer cell lines, and telomerase activity is associated with tumorigenesis. Telomere elongation is also believed to be an important contributor to the genomic stability and indefinite self renewal of iPS cells. 1 μM MST-312 was shown to effectively reduce telomere length and inhibit proliferation in U937 cells.