2.0 2012-05-31 14:25:00 -0600 2015-06-04 15:11:33 -0600 ECMDB20053 M2MDB000902 2,2-Dichloroacetaldehyde 2,2-dichloroacetaldehyde is a member of the chemical class known as Organochlorides. These are organic compounds containing a chlorine atom. N2,3-Ethenoguanine (epsilon G) is a product of vinyl chloride reaction with DNA in vivo and of its ultimate metabolite, chloroacetaldehyde, in vitro. (PMID 2013138). It is a bifunctional compound, making it a useful building block chemical. 2, 2-Dichloroacetaldehyde 2,2-Dichloro-Acetaldehyde 2-Chloroacetaldehyde 2-Chloroethanal a,a-Dichloroacetaldehyde a-Chloroacetyl chloride Alpha,alpha-Dichloroacetaldehyde Alpha-Chloroacetyl chloride CH2ClCOCl CHCl2CHO Chloracetyl chloride Chloraldehyde Chlorid kyseliny chloroctove Chlorid kyseliny chloroctove [czech] Chloro-Acetyl chloride Chloroacetate chloride Chloroacetic acid chloride Chloroacetic chloride Chloroacetyl chloride [UN1752] [Poison] Chloroaldehyde Chloroethanal Chloroethanoyl chloride Chlorure de chloracetyle Chlorure de chloracetyle [french] Dichloro-Acetaldehyde Dichloroacetaldehyde InChI=1/C2H2Cl2O/c3-1-2(4)5/h1H Monochloroacetaldehyde Monochloroacetyl chloride α,α-Dichloroacetaldehyde α-Chloroacetyl chloride C2H3Cl3 133.404 131.930033217 1,1,2-trichloroethane 1,1, 2-trichloroethane 79-02-7 ClCC(Cl)Cl InChI=1S/C2H3Cl3/c3-1-2(4)5/h2H,1H2 UBOXGVDOUJQMTN-UHFFFAOYSA-N Liquid Inner membrane Membrane Outer membrane logp 2.02 ALOGPS logs -1.66 ALOGPS solubility 2.93e+00 g/l ALOGPS melting_point -37.5 oC logp 2.17 ChemAxon iupac 1,1,2-trichloroethane ChemAxon average_mass 133.404 ChemAxon mono_mass 131.930033217 ChemAxon smiles ClCC(Cl)Cl ChemAxon formula C2H3Cl3 ChemAxon inchi InChI=1S/C2H3Cl3/c3-1-2(4)5/h2H,1H2 ChemAxon inchikey UBOXGVDOUJQMTN-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 25.71 ChemAxon polarizability 10.43 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon glutathione metabolism II The biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione. This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione. Glutathione can then be degraded into various different glutathione containg compounds by reacting with a napthalene through a glutathione S-transferase PW001927 Metabolic Specdb::CMs 112450 Specdb::CMs 125940 Specdb::EiMs 846 Specdb::NmrOneD 2646 Specdb::NmrOneD 3333 Specdb::NmrOneD 168561 Specdb::NmrOneD 168562 Specdb::NmrOneD 168563 Specdb::NmrOneD 168564 Specdb::NmrOneD 168565 Specdb::NmrOneD 168566 Specdb::NmrOneD 168567 Specdb::NmrOneD 168568 Specdb::NmrOneD 168569 Specdb::NmrOneD 168570 Specdb::NmrOneD 168571 Specdb::NmrOneD 168572 Specdb::NmrOneD 168573 Specdb::NmrOneD 168574 Specdb::NmrOneD 168575 Specdb::NmrOneD 168576 Specdb::NmrOneD 168577 Specdb::NmrOneD 168578 Specdb::NmrOneD 168579 Specdb::NmrOneD 168580 Specdb::MsMs 27287 Specdb::MsMs 27288 Specdb::MsMs 27289 Specdb::MsMs 33845 Specdb::MsMs 33846 Specdb::MsMs 33847 Specdb::MsMs 3393448 Specdb::MsMs 3393449 Specdb::MsMs 3393450 Specdb::MsMs 3394735 Specdb::MsMs 3394736 Specdb::MsMs 3394737 6576 6326 C14858 CHLOROACETALDEHYDE Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 Singer, B., Kusmierek, J. T., Folkman, W., Chavez, F., Dosanjh, M. K. (1991). "Evidence for the mutagenic potential of the vinyl chloride induced adduct, N2, 3-etheno-deoxyguanosine, using a site-directed kinetic assay." Carcinogenesis 12:745-747. 2013138 Glutathione S-transferase P0A9D2 GST_ECOLI gst http://ecmdb.ca/proteins/P0A9D2.xml GSH-dependent disulfide bond oxidoreductase P77526 yfcG http://ecmdb.ca/proteins/P77526.xml 2,2-Dichloroacetaldehyde + Glutathione <> S-(2,2-Dichloro-1-hydroxy)ethyl glutathione R07091 2,2-Dichloroacetaldehyde + Glutathione <> S-(2-Chloroacetyl)glutathione + Hydrochloric acid R07093 Glutathione + 2,2-Dichloroacetaldehyde > S-(Formylmethyl)glutathione PW_R005505