2.0 2012-05-31 14:05:03 -0600 2015-09-13 12:56:14 -0600 ECMDB04102 M2MDB000610 Menaquinone Menaquinone is a naphthoquinone without the isoprenoid side chain and biological activity. It is sometimes called vitamin K3, although derivatives of naphthoquinone without the sidechain in the 3-position cannot exert all the functions of the K vitamins. 2-Methyl-1,4-naftochinon 2-Methyl-1,4-naphthalendione 2-Methyl-1,4-naphthalenedione 2-Methyl-1,4-naphthochinon 2-Methyl-1,4-naphthodione 2-Methyl-1,4-naphthoquinone 2-Methylnaphthoquinone 3-Methyl-1,4-naphthoquinone Aquakay Aquinone Hemodal Juva-K K-Thrombyl K-Vitan Kaergona Kanone Kappaxan Kappaxin Karcon Kareon Kativ-G Kayklot Kaykot Kaynone Kayquinone Kipca Kipca-Oil Soluble Klottone Koaxin Kolklot Menadion Menadione Menaphthene Menaphthon Menaphthone Menaphtone Menaquinone Menaquinone O Mitenon Mitenone MK-8 MNQ Panosine Prokayvit Synkay Thyloquinone Vitamin K0 Vitamin K2 Vitamin K3 Vitamin K3: 1,4-Dihydro-1,4-dioxo-2-methylnaphthalene Vitamin K₂ C11H8O2 172.18 172.0524295 2-methyl-1,4-dihydronaphthalene-1,4-dione menadione 58-27-5 CC1=CC(=O)C2=CC=CC=C2C1=O InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 MJVAVZPDRWSRRC-UHFFFAOYSA-N Solid Outer membrane Inner membrane logp 1.91 ALOGPS logs -2.53 ALOGPS solubility 5.04e-01 g/l ALOGPS melting_point 107 oC logp 1.89 ChemAxon pka_strongest_acidic 12.94 ChemAxon pka_strongest_basic -7.2 ChemAxon iupac 2-methyl-1,4-dihydronaphthalene-1,4-dione ChemAxon average_mass 172.18 ChemAxon mono_mass 172.0524295 ChemAxon smiles CC1=CC(=O)C2=CC=CC=C2C1=O ChemAxon formula C11H8O2 ChemAxon inchi InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 ChemAxon inchikey MJVAVZPDRWSRRC-UHFFFAOYSA-N ChemAxon polar_surface_area 34.14 ChemAxon refractivity 50.54 ChemAxon polarizability 17.64 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 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 Porphyrin and chlorophyll metabolism ec00860 Specdb::CMs 1233 Specdb::CMs 1423 Specdb::CMs 1452 Specdb::CMs 13996 Specdb::CMs 29011 Specdb::CMs 31366 Specdb::CMs 31367 Specdb::CMs 31368 Specdb::CMs 172123 Specdb::EiMs 1009 Specdb::NmrOneD 1785 Specdb::NmrOneD 2498 Specdb::NmrOneD 3195 Specdb::NmrOneD 345248 Specdb::NmrOneD 345249 Specdb::NmrOneD 345250 Specdb::NmrOneD 345251 Specdb::NmrOneD 345252 Specdb::NmrOneD 345253 Specdb::NmrOneD 345254 Specdb::NmrOneD 345255 Specdb::NmrOneD 345256 Specdb::NmrOneD 345257 Specdb::NmrOneD 345258 Specdb::NmrOneD 345259 Specdb::NmrOneD 345260 Specdb::NmrOneD 345261 Specdb::NmrOneD 345262 Specdb::NmrOneD 345263 Specdb::NmrOneD 345264 Specdb::NmrOneD 345265 Specdb::NmrOneD 345266 Specdb::NmrOneD 345267 Specdb::MsMs 1801 Specdb::MsMs 1802 Specdb::MsMs 1803 Specdb::MsMs 5575 Specdb::MsMs 19895 Specdb::MsMs 19896 Specdb::MsMs 19897 Specdb::MsMs 21446 Specdb::MsMs 21447 Specdb::MsMs 21448 Specdb::MsMs 374287 Specdb::MsMs 450779 Specdb::MsMs 2701285 Specdb::MsMs 2701286 Specdb::MsMs 2701287 Specdb::MsMs 3007340 Specdb::MsMs 3007341 Specdb::MsMs 3007342 Specdb::NmrTwoD 1725 HMDB01892 4055 3915 C00828 28869 CPD-9728 VK3 Menadione 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." 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Kokai Tokkyo Koho (1986), 4 pp. http://hmdb.ca/system/metabolites/msds/000/001/483/original/HMDB01892.pdf?1358894850 Protoporphyrinogen oxidase P0ACB4 HEMG_ECOLI hemG http://ecmdb.ca/proteins/P0ACB4.xml Anaerobic dimethyl sulfoxide reductase chain A P18775 DMSA_ECOLI dmsA http://ecmdb.ca/proteins/P18775.xml Anaerobic dimethyl sulfoxide reductase chain B P18776 DMSB_ECOLI dmsB http://ecmdb.ca/proteins/P18776.xml Anaerobic dimethyl sulfoxide reductase chain C P18777 DMSC_ECOLI dmsC http://ecmdb.ca/proteins/P18777.xml Ubiquinone/menaquinone biosynthesis methyltransferase ubiE P0A887 UBIE_ECOLI ubiE http://ecmdb.ca/proteins/P0A887.xml Protein PhsC homolog P77409 PHSC_ECOLI ydhU http://ecmdb.ca/proteins/P77409.xml Dimethyl sulfide + Menaquinone + Water > Dimethyl sulfoxide + Menaquinol 6 Protoporphyrinogen IX + 3 Menaquinone > Protoporphyrin IX +3 Menaquinol 6 R09489 Menaquinone + Water + Dimethyl sulfide <> Menaquinol 6 R09501 Protoporphyrinogen IX + 3 Menaquinone + 3 Menaquinone <> Protoporphyrin IX +3 Menaquinol 6 R09489 2 2-Demethylmenaquinone 8 + S-Adenosylmethionine <> Menaquinone + S-Adenosylhomocysteine