KEGG   ENZYME: 2.1.1.374
Entry
EC 2.1.1.374                Enzyme                                 
Name
2-heptyl-1-hydroxyquinolin-4(1H)-one methyltransferase;
htm (gene name)
Class
Transferases;
Transferring one-carbon groups;
Methyltransferases
Sysname
S-adenosyl-L-methionine:2-heptyl-1-hydroxyquinolin-4(1H)-one methyltransferase
Reaction(IUBMB)
S-adenosyl-L-methionine + 2-heptyl-1-hydroxyquinolin-4(1H)-one = S-adenosyl-L-homocysteine + 2-heptyl-1-methoxyquinolin-4(1H)-one [RN:R12667]
Reaction(KEGG)
R12667
Substrate
S-adenosyl-L-methionine [CPD:C00019];
2-heptyl-1-hydroxyquinolin-4(1H)-one
Product
S-adenosyl-L-homocysteine [CPD:C00021];
2-heptyl-1-methoxyquinolin-4(1H)-one [CPD:C22317]
Comment
The enzyme, found in mycobacteria, is a member of a family of heterocyclic toxin methyltransferases. It is involved in defense against several antimicrobial natural compounds and drugs. 4-Hydroxyquinolin-2(1H)-one, 2-heptylquinolin-4(1H)-one, 2-heptyl-3-hydroxyquinolin-4(1H)-one (the "Pseudomonas quinolone signal", PQS) and the flavonol quercetin are also O-methylated, albeit with lower activity [2]. The enzyme also N-methylates the bactericidal compound 3-methyl-1-oxo-2-[3-oxo-3-(pyrrolidin-1-yl)propyl]-1,5-dihydrobenzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile [1].
History
EC 2.1.1.374 created 2020
Orthology
K24667  2-heptyl-1-hydroxyquinolin-4(1H)-one methyltransferase
Genes
MTURv0560c
MTVRVBD_0560c
MTCMT0586
MRAMRA_0567
MTFTBFG_10570
MTBTBMG_00565
MTKTBSG_00571
MTZTBXG_000562
MTGMRGA327_03515
MTIMRGA423_03505
MTECCDC5079_0526
MTURCFBS_0584
MTLCCDC5180_0518
MTOMTCTRI2_0568
MTDUDA_0560c
MTNERDMAN_0613
MTJJ112_03000
MTUBMT7199_0574
MTUCJ113_04005
MTUEJ114_02995
MTXM943_02900
MTUHI917_03995
MTULTBHG_00557
MTUTHKBT1_0584
MTUUHKBT2_0584
MTQHKBS1_0584
MBOBQ2027_MB0575C
MBBBCG_0605c
MBTJTY_0575
MBMBCGMEX_0576c
MBKK60_005940
MBXBCGT_0343
MAFMAF_05670
MMICRN08_0626
MCEMCAN_05631
MCQBN44_10621
MCVBN43_10612
MCXBN42_20299
MCZBN45_10627
MPAMAP_0125c
MAOMAP4_3749
MAVIRC58_18615
MAVURE97_18660
MAVMAV_0119
MITOCO_01230
MIAOCU_01270
MIDMIP_00388
MYOOEM_01320
MCHIAN480_00665
MIROCQ_01220
MMALCKJ54_00535
MMANMMAN_43710
MSAMycsm_02369
MULMUL_0662
MMIMMAR_0909
MMAEMMARE11_08590
MMMW7S_00600
MLIMULP_00937
MKNMKAN_16420
MYVG155_11960
MYEAB431_10915
MGOAFA91_26865
MHADB586_19215
MDXBTO20_22865
MSHGMSG_00788
MFJMFLOJ_26820
MSTOMSTO_30690
MSIMMSIM_16860
MSAKMSAS_34690
MKUI2456_00925 I2456_04650
MGROFZ046_16315
MXEMYXE_02970 MYXE_17930
MNVMNVI_14790
MPAGC0J29_04925
MNMMNVM_12680
MGORH0P51_04530
MCOOMCOO_00570 MCOO_45570 MCOO_45580
MBAIMB901379_00779(bchM_1)
MSEOMSEO_39320
MPSEMPSD_10400
MSHOMSHO_26690
MHEKJMUB5695_00259
MGAUMGALJ_06920
MLJMLAC_35930
MBRDMBRA_07810 MBRA_47430
MKRMKOR_16730
MMAMK3U93_08185 K3U93_20575
MHOLK3U96_16650
MHERK3U94_03230
MSENK3U95_02110 K3U95_02120 K3U95_17845
MPAEK0O64_10575
MOTLTS72_09505
MVMMJO54_03250
MRFMJO55_10060
MPAAMKK62_16090
MCROMI149_11440
MSMMSMEG_2539
MSGMSMEI_2479
MSBLJ00_12640
MSNLI99_12640
MSHLI98_12645
MCBMycch_1969
MNED174_11235
MYNMyAD_11020
MFTXA26_24570
MPHLMPHLCCUG_02170(tpm)
MLLB1R94_18185
MRHMycrhN_5771
MHASMHAS_02535(ubiG_2)
MAUUNCTC10437_02077
MMAGMMAD_22030
MAICMAIC_18860
MALVMALV_14720
MPSCMPSYJ_44270
MARZMARA_18220
MGADMGAD_17110
MHEVMHEL_44010
MSARMSAR_31760
MAUBMAUB_55180
MPHUMPHO_13970
MMATMMAGJ_55410
MBOKMBOE_50310
MFGK6L26_20265
MSEIMSEDJ_34330 MSEDJ_59000
MFLVNCTC10271_03297
MCEEMCEL_15170
MABMAB_0393 MAB_2834c
MMVMYCMA_08040 MYCMA_13185
MABBMASS_0387 MASS_2775
MABLMMASJCM_0386 MMASJCM_2793
MCHEBB28_01940 BB28_14145
MIZBAB75_02490 BAB75_15285
MSTEMSTE_00354 MSTE_02782
MSAOMYCSP_01760
MSALDSM43276_00346(tehB)
MJDJDM601_0554
MTER4434518_00554(tehB)
MMINMMIN_22630
MHIBMHIB_00540
MPAKMIU77_12410
NNONONO_c28860
NTPCRH09_23710
NWLNWFMUON74_51090
SROIIAG44_40890
APRTMUY14_09075
 » show all
Reference
1  [PMID:27432954]
  Authors
Warrier T, Kapilashrami K, Argyrou A, Ioerger TR, Little D, Murphy KC, Nandakumar M, Park S, Gold B, Mi J, Zhang T, Meiler E, Rees M, Somersan-Karakaya S, Porras-De Francisco E, Martinez-Hoyos M, Burns-Huang K, Roberts J, Ling Y, Rhee KY, Mendoza-Losana A, Luo M, Nathan CF.
  Title
N-methylation of a bactericidal compound as a resistance mechanism in Mycobacterium tuberculosis.
  Journal
Proc Natl Acad Sci U S A 113:E4523-30 (2016)
DOI:10.1073/pnas.1606590113
  Sequence
[mtu:Rv0560c]
Reference
2  [PMID:33064871]
  Authors
Sartor P, Bock J, Hennecke U, Thierbach S, Fetzner S.
  Title
Modification of the Pseudomonas aeruginosa toxin 2-heptyl-1-hydroxyquinolin-4(1H)-one and other secondary metabolites by methyltransferases from mycobacteria.
  Journal
FEBS J (2020)
DOI:10.1111/febs.15595
  Sequence
[mtu:Rv0560c] [mab:MAB_2834c]
Other DBs
ExplorEnz - The Enzyme Database: 2.1.1.374
IUBMB Enzyme Nomenclature: 2.1.1.374
ExPASy - ENZYME nomenclature database: 2.1.1.374
BRENDA, the Enzyme Database: 2.1.1.374

DBGET integrated database retrieval system