2.0 2015-06-04 15:13:44 -0600 2015-07-23 12:06:48 -0600 ECMDB23762 M2MDB004197 Alkanesulfonate Alkanesulfonic acid Alkanesulphonate Alkanesulphonic acid C18H24O3 288.3814 288.172544634 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-dione 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-dione COC1=CC(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=O InChI=1S/C18H24O3/c1-12(2)7-6-8-13(3)9-10-15-14(4)16(19)11-17(21-5)18(15)20/h7,9,11H,6,8,10H2,1-5H3/b13-9+ GKCNNWJPOJGTLV-UKTHLTGXSA-N logp 4.16 ALOGPS logs -4.38 ALOGPS solubility 1.20e-02 g/l ALOGPS logp 4.28 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac 3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-dione ChemAxon average_mass 288.3814 ChemAxon mono_mass 288.172544634 ChemAxon smiles COC1=CC(=O)C(C)=C(C\C=C(/C)CCC=C(C)C)C1=O ChemAxon formula C18H24O3 ChemAxon inchi InChI=1S/C18H24O3/c1-12(2)7-6-8-13(3)9-10-15-14(4)16(19)11-17(21-5)18(15)20/h7,9,11H,6,8,10H2,1-5H3/b13-9+ ChemAxon inchikey GKCNNWJPOJGTLV-UKTHLTGXSA-N ChemAxon polar_surface_area 43.37 ChemAxon refractivity 89.47 ChemAxon polarizability 33.33 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 3 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Sulfur metabolism The sulfur metabolism pathway starts in three possible ways. The first is the uptake of sulfate through an active transport reaction via a sulfate transport system containing an ATP-binding protein which hydrolyses ATP. Sulfate is converted by the sulfate adenylyltransferase enzymatic complex to adenosine phosphosulfate through the addition of adenine from a molecule of ATP, along with one phosphate group. Adenosine phosphosulfate is further converted to phoaphoadenosine phosphosulfate through an ATP hydrolysis and dehydrogenation reaction by the adenylyl-sulfate kinase. Phoaphoadenosine phosphosulfate is finally dehydrogenated and converted to sulfite by phosphoadenosine phosphosulfate reductase. This reaction requires magnesium, and adenosine 3',5'-diphosphate is the bi-product. A thioredoxin is also oxidized. Sulfite can also be produced from the dehydrogenation of cyanide along with the conversion of thiosulfate to thiocyanate by the thiosulfate sulfurtransferase enzymatic complex. Sulfite next undergoes a series of reactions that lead to the production of pyruvic acid, which is a precursor for pathways such as gluconeogenesis. The first reaction in this series is the conversion of sulfite to hydrogen sulfide through hygrogenation and the deoxygenation of sulfite to form a water molecule. The reaction is catalyzed by the sulfite reductase [NADPH] flavoprotein alpha and beta components. Siroheme, 4Fe-4S, flavin mononucleotide, and FAD function as cofactors or prosthetic groups. Hydrogen sulfide next undergoes dehydrogenation in a reversible reaction to form L-Cysteine and acetic acid, via the cysteine synthase complex and the coenzyme pyridoxal 5'-phosphate. L-Cysteine is dehydrogenated and converted to 2-aminoacrylic acid (a bronsted acid) and hydrogen sulfide(which may be reused) by a larger enzymatic complex composed of cysteine synthase A/B, protein malY, cystathionine-β-lyase, and tryptophanase, along with the coenzyme pyridoxal 5'-phosphate. 2-aminoacrylic acid isomerizes to 2-iminopropanoate, which along with a water molecule and a hydrogen ion is lastly converted to pyruvic acid and ammonium in a spontaneous fashion. The second possible initial starting point for sulfur metabolism is the import of taurine(an alternate sulfur source) into the cytoplasm via the taurine ABC transporter complex. Taurine, oxoglutaric acid, and oxygen are converted to sulfite by the alpha-ketoglutarate-dependent taurine dioxygenase. Carbon dioxide, succinic acid, and aminoacetaldehyde are bi-products of this reaction. Sulfite next enters pyruvic acid synthesis as already described. The third variant of sulfur metabolism starts with the import of an alkyl sulfate into the cytoplasm via an aliphatic sulfonate ABC transporter complex which hydrolyses ATP. The alkyl sulfate is dehydrogenated and along with oxygen is converted to sulfite and an aldehyde by the FMNH2-dependent alkanesulfonate monooxygenase enzyme. Water and flavin mononucleotide(which is used in a subsequent reaction as a prosthetic group) are also produced. Sulfite is next converted to pyruvic acid by the process already described. PW000922 ec00920 Metabolic Specdb::CMs 33817 Specdb::CMs 170461 Specdb::MsMs 27230 Specdb::MsMs 27231 Specdb::MsMs 27232 Specdb::MsMs 33788 Specdb::MsMs 33789 Specdb::MsMs 33790 C15521 FMN reductase P80644 SSUE_ECOLI ssuE http://ecmdb.ca/proteins/P80644.xml Alkanesulfonate monooxygenase P80645 SSUD_ECOLI ssuD http://ecmdb.ca/proteins/P80645.xml Alkanesulfonate + FMNH + Oxygen <> Aldehyde + Flavin Mononucleotide + Sulfite + Water R07210 Alkanesulfonate + FMNH + Oxygen <> Aldehyde + Flavin Mononucleotide + Sulfite + Water