2.02012-05-31 14:05:03 -06002015-09-13 12:56:14 -0600ECMDB04102M2MDB000610MenaquinoneMenaquinone 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-naftochinon2-Methyl-1,4-naphthalendione2-Methyl-1,4-naphthalenedione2-Methyl-1,4-naphthochinon2-Methyl-1,4-naphthodione2-Methyl-1,4-naphthoquinone2-Methylnaphthoquinone3-Methyl-1,4-naphthoquinoneAquakayAquinoneHemodalJuva-KK-ThrombylK-VitanKaergonaKanoneKappaxanKappaxinKarconKareonKativ-GKayklotKaykotKaynoneKayquinoneKipcaKipca-Oil SolubleKlottoneKoaxinKolklotMenadionMenadioneMenaphtheneMenaphthonMenaphthoneMenaphtoneMenaquinoneMenaquinone OMitenonMitenoneMK-8MNQPanosineProkayvitSynkayThyloquinoneVitamin K0Vitamin K2Vitamin K3Vitamin K3: 1,4-Dihydro-1,4-dioxo-2-methylnaphthaleneVitamin K<sub>2</sub>C11H8O2172.18172.05242952-methyl-1,4-dihydronaphthalene-1,4-dionemenadione58-27-5CC1=CC(=O)C2=CC=CC=C2C1=OInChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3MJVAVZPDRWSRRC-UHFFFAOYSA-NSolidOuter membraneInner membranelogp1.91logs-2.53solubility5.04e-01 g/lmelting_point107 oClogp1.89pka_strongest_acidic12.94pka_strongest_basic-7.2iupac2-methyl-1,4-dihydronaphthalene-1,4-dioneaverage_mass172.18mono_mass172.0524295smilesCC1=CC(=O)C2=CC=CC=C2C1=OformulaC11H8O2inchiInChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3inchikeyMJVAVZPDRWSRRC-UHFFFAOYSA-Npolar_surface_area34.14refractivity50.54polarizability17.64rotatable_bond_count0acceptor_count2donor_count0physiological_charge0formal_charge0Sulfur metabolismThe 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.PW000922ec00920MetabolicPorphyrin and chlorophyll metabolismec00860Specdb::CMs1233Specdb::CMs1423Specdb::CMs1452Specdb::CMs13996Specdb::CMs29011Specdb::CMs31366Specdb::CMs31367Specdb::CMs31368Specdb::CMs172123Specdb::EiMs1009Specdb::NmrOneD1785Specdb::NmrOneD2498Specdb::NmrOneD3195Specdb::NmrOneD345248Specdb::NmrOneD345249Specdb::NmrOneD345250Specdb::NmrOneD345251Specdb::NmrOneD345252Specdb::NmrOneD345253Specdb::NmrOneD345254Specdb::NmrOneD345255Specdb::NmrOneD345256Specdb::NmrOneD345257Specdb::NmrOneD345258Specdb::NmrOneD345259Specdb::NmrOneD345260Specdb::NmrOneD345261Specdb::NmrOneD345262Specdb::NmrOneD345263Specdb::NmrOneD345264Specdb::NmrOneD345265Specdb::NmrOneD345266Specdb::NmrOneD345267Specdb::MsMs1801Specdb::MsMs1802Specdb::MsMs1803Specdb::MsMs5575Specdb::MsMs19895Specdb::MsMs19896Specdb::MsMs19897Specdb::MsMs21446Specdb::MsMs21447Specdb::MsMs21448Specdb::MsMs374287Specdb::MsMs450779Specdb::MsMs2701285Specdb::MsMs2701286Specdb::MsMs2701287Specdb::MsMs3007340Specdb::MsMs3007341Specdb::MsMs3007342Specdb::NmrTwoD1725HMDB0189240553915C0082828869CPD-9728VK3MenadioneKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510Winder, 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?1358894850Protoporphyrinogen oxidaseP0ACB4HEMG_ECOLIhemGhttp://ecmdb.ca/proteins/P0ACB4.xmlAnaerobic dimethyl sulfoxide reductase chain AP18775DMSA_ECOLIdmsAhttp://ecmdb.ca/proteins/P18775.xmlAnaerobic dimethyl sulfoxide reductase chain BP18776DMSB_ECOLIdmsBhttp://ecmdb.ca/proteins/P18776.xmlAnaerobic dimethyl sulfoxide reductase chain CP18777DMSC_ECOLIdmsChttp://ecmdb.ca/proteins/P18777.xmlUbiquinone/menaquinone biosynthesis methyltransferase ubiEP0A887UBIE_ECOLIubiEhttp://ecmdb.ca/proteins/P0A887.xmlProtein PhsC homologP77409PHSC_ECOLIydhUhttp://ecmdb.ca/proteins/P77409.xmlDimethyl sulfide + Menaquinone + Water > Dimethyl sulfoxide + Menaquinol 6Protoporphyrinogen IX + 3 Menaquinone > Protoporphyrin IX +3 Menaquinol 6R09489Menaquinone + Water + Dimethyl sulfide <> Menaquinol 6R09501 Protoporphyrinogen IX + 3 Menaquinone + 3 Menaquinone <> Protoporphyrin IX +3 Menaquinol 6R094892 2-Demethylmenaquinone 8 + S-Adenosylmethionine <> Menaquinone + S-Adenosylhomocysteine