Basic information
- CAS
251456-60-7- Standard SMILES
CN(C)c1ccc(C(=O)NCCCCCCC(=O)NO)cc1- InChIKey
MXWDSZWTBOCWBK-UHFFFAOYSA-N- Molecular formula
- C16H25N3O3
- Average molar mass
- 307.39 g/mol
- Monoisotopic mass
- 307.18959167
Overview
4-(dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]benzamide is a benzamide resulting from the formal condensation of the carboxy group of 4-(dimethylamino)benzoic acid with the amino group of 7-amino-N-hydroxyheptanamide. It is a potent inhibitor of histone deacetylases and induces cell cycle arrest and apoptosis in several human cancer cell lines. It has a role as an antineoplastic agent, an EC 3.5.1.98 (histone deacetylase) inhibitor and an apoptosis inducer. It is a secondary carboxamide, a member of benzamides, a hydroxamic acid and a tertiary amino compound.
Names & identifiers
- Preferred name
- 4-(dimethylamino)-N-(7-(hydroxyamino)-7-oxoheptyl)benzamide
- IUPAC
- 4-(dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]benzamide
- English name
- M344
- Molecular formula
- C16H25N3O3
- Molecular weight
- 307.39
Names & synonyms
4-(dimethylamino)-n-[7-(hydroxyamino)-7-oxoheptyl]benzamide4-(dimethylamino)-N-(7-(hydroxyamino)-7-oxoheptyl)benzamideHistone Deacetylase Inhibitor IIIN-Hydroxy-7-(4-dimethylaminobenzoyl)aminoheptanamide4-Dimethylamino-N-(6-hydroxycarbamoylhexyl)benzamideCHEBI:1255627-{[4-(DIMETHYLAMINO)PHENYL]FORMAMIDO}-N-HYDROXYHEPTANAMIDE7-((4-(dimethylamino)phenyl)formamido)-N-hydroxyheptanamideRefChem:974374-(dimethylamino)-NHAOBzNH2251456-60-7m344
Show more names
CS-661MS 344MS 344, D237M344 (D 237)M344 USP/EP/BPM344, 10 mM in DMSOM344, HDAC inhibitorM 344 (enzyme inhibitor)
M 344M-344Benzamide, 4-(dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]-MFCD03453554J8W4VF5ZEJD 237;MS 344CHEMBL140000CS-1342
Database identifiers
- CAS
251456-60-7- PubChem CID
- 3994
- DTXSID
DTXSID90274415- ChEMBL
CHEMBL140000- ChEBI
CHEBI:125562- UNII
- J8W4VF5ZEJ
- Nikkaji
- J1.216.507B
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 81.7 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 340
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 161 ℃ · 161℃
- Density
- 1.137 · 1.137±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 10 mg/mL, · DMSO: soluble10mg/mL, clear
- pka
- 9.48 · 9.48±0.20(Predicted)
- form
- White solid
- color
- white to beige
- Sensitive
- Light Sensitive
- 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
- SMILES
- CN(C)c1ccc(cc1)C(=O)NCCCCCCC(=O)NO
- CAS DataBase Reference
- 251456 · 251456-60-7
- FDA UNII
- 8 W4VF5ZEJ · J8W4VF5ZEJ
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P302+P352-P305+P351+P338-P321-P405-P501
- WGK Germany
- 3 · 3
- HS Code
- 2928 · 2928.00.2500
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- hs_code
- 2928.00.2500
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P302+P352-P305+P351+P338-P321-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCompounds that inhibit HISTONE DEACETYLASES. This class of drugs may influence gene expression by increasing the level of acetylated HISTONES in specific CHROMATIN domains.
Applications
UsesHistone deacetylase inhibitor III. A cell-permeable amide analog of Trichostatin A that potently inhibits HDACs.
UsesM 344 is an inhibitor of histone deacetylases (HDACs), inhibiting maize HDAC (IC50 = 100 nM) as well as human HDAC1 (IC50 = 46 nM). It shows a three-fold selectivity for inhibition of HDAC6 over HDAC1. M 344 enhances the sensitivity of human squamous carcinoma cells to radiation and promotes cell cycle arrest and apoptosis in human endometrial cancer and ovarian cancer cells (ED50 = 2.3 μM).
General DescriptionA cell-permeable amide analog of Trichostatin A (Cat. No. 647925) that potently inhibits histone deacetylases (IC50 = 40 nM for rat liver HDAC and IC50 = 100 nM for maize HD). Induces differentiation and inhibits proliferation (~2 μM) of murine erythroleukemia cells.
Suppliers95 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
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Additional notes
DefinitionChEBI: 4-(dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]benzamide is a benzamide resulting from the formal condensation of the carboxy group of 4-(dimethylamino)benzoic acid with the amino group of 7-amino-N-hydroxyheptanamide. It is a potent inhibitor of histone deacetylases and induces cell cycle arrest and apoptosis in several human cancer cell lines. It has a role as an apoptosis inducer, an antineoplastic agent and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a member of benzamides, a hydroxamic acid, a secondary carboxamide and a tertiary amino compound.
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