7-{[4-(dimethylamino)phenyl]formamido}-N-hydroxyheptanamide

• ChemBase ID: 153871
• Molecular Formular: C16H25N3O3
• Molecular Mass: 307.388
• Monoisotopic Mass: 307.18959168
• SMILES: CN(C)c1ccc(cc1)C(=O)NCCCCCCC(=O)NO
• Canonical SMILES: ONC(=O)CCCCCCNC(=O)c1ccc(cc1)N(C)C
• InChI: InChI=1S/C16H25N3O3/c1-19(2)14-10-8-13(9-11-14)16(21)17-12-6-4-3-5-7-15(20)18-22/h8-11,22H,3-7,12H2,1-2H3,(H,17,21)(H,18,20)
• InChIKey: MXWDSZWTBOCWBK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{[4-(dimethylamino)phenyl]formamido}-N-hydroxyheptanamide
• IUPAC Traditional name: 7-{[4-(dimethylamino)phenyl]formamido}-N-hydroxyheptanamide
• Synonyms: 4-(Dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]-benzamide; MS 344, D237; N-Hydroxy-7-(4-dimethylaminobenzoyl)-aminoheptanamide; M344; M344; 4-(Dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]benzamide; D 237; M 344; M 344 (Enzyme Inhibitor); MS 344; N-Hydroxy-7-(4-dimethylaminobenzoyl)aminoheptanamide

Database IDs

• CAS Number: 251456-60-7
• MDL Number: MFCD03453554
• PubChem SID: 162248010
• PubChem CID: 3994

CALCULATED PROPERTIES

• Acid pKa: 8.907539
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.678456
• LogD (pH = 7.4): 1.669563
• Log P: 1.682845
• Molar Refractivity: 87.3905 cm^3
• Polarizability: 32.717518 Å^3
• Polar Surface Area: 81.67 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble10 mg/mL, clear
• Apperance: white to beige powder

Safety Information

• Storage Condition: protect from light
• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: HDAC

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C16H25N3O3

DETAILS

Sigma Aldrich - M5820

Biochem/physiol Actions
M344 is a HDAC inhibitor; subtype selective for HDAC6 over HDAC1. M344 inhibits HDAC (IC50 = 100 nM) and also inhibits hyperacetylation of histone H4, terminal cell differentiation, transcription (γ-globin), and tumor cell death.

Toronto Research Chemicals - H941480

Histone deacetylase inhibitor III. A cell-permeable amide analog of Trichostatin A that potently inhibits HDACs.

REFERENCES

• Jung, M., et al.: J. Med. Chem., 42, 4669 (1999)
• Ramiszewski, S.W., et al.: J. Med. Chem., 45, 753 (1999)
• Gregoretti, I., et al.: J. Mol. Biol., 338, 17 (1999)
• Gennadios, H., et al.: Biochemistry, 45, 7940 (1999)
• Bottomley, M., et al.: J. Biol. Chem.,