Basic information
- CAS
176046-79-0- Standard SMILES
COc1[nH]c(C(Cl)(Cl)Cl)c(Cl)c(=O)c1Cl- InChIKey
GUYGGZGIKZIRFO-UHFFFAOYSA-N- Molecular formula
- C7H4Cl5NO2
- Average molar mass
- 311.4 g/mol
- Monoisotopic mass
- 308.868467
Overview
structure in first source
Names & identifiers
- Preferred name
- 4-O-Demethylpenclomedine
- IUPAC
- 3,5-dichloro-2-methoxy-6-(trichloromethyl)-1H-pyridin-4-one
Names & synonyms
4-O-Demethylpenclomedine176046-79-04-Demethylpenclomedine4-Dmpen4-Dm-penDM-PENNSC-682691XUK71J2M0Q4-Pyridinol, 3,5-dichloro-2-methoxy-6-(trichloromethyl)-RefChem:5260573,5-dichloro-2-methoxy-6-(trichloromethyl)-1,4-dihydropyridin-4-oneDMPEN
Show more names
3,5-dichloro-2-methoxy-6-(trichloromethyl)pyridin-4-ol3,5-dichloro-2-methoxy-6-(trichloromethyl)-1H-pyridin-4-one3,5-dichloro-2-methoxy-6-(trichloromethyl)pyridin-4(1h)-oneUNII-XUK71J2M0QNSC6826914-Demethyl-penclomedineCHEMBL11122orb3136814
Database identifiers
- CAS
176046-79-0- PubChem CID
- 388136
- DTXSID
DTXSID90327758- ChEMBL
CHEMBL11122- UNII
- XUK71J2M0Q
- Nikkaji
- J841.915I
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 38.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 368
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Chemistry & industry
Pharmacology
Mechanism of Action
DMPEN (4,o-demethylpenclomedine) is the highly reactive principal alkylating metabolite of Penclomedine (PEN), a multichlorinated alpha-picoline derivative. DM-PEN’s proposed mechanism of action begins with activation by free radical formation in the liver, where it is then transported to tumor cells via the circulation system. The free radical moiety forms an adduct with DNA, and interstrand crosslinking occurs through the 5-chloro moiety. The 5-chloro moiety is then activated by keto-enol tautomerism, producing the alkylating group, an alpha-haloketo function.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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