Reaction participants Show >> << Hide
- Name help_outline menaquinone-9 Identifier CHEBI:44147 (CAS: 523-39-7) help_outline Charge 0 Formula C56H80O2 InChIKeyhelp_outline WCRXHNIUHQUASO-UVZVDVBNSA-N SMILEShelp_outline C1(=O)C(C)=C(C(=O)C2=CC=CC=C12)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline AH2 Identifier CHEBI:17499 Charge 0 Formula RH2 SMILEShelp_outline *([H])[H] 2D coordinates Mol file for the small molecule Search links Involved in 2,812 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline β-dihydromenaquinone-9 Identifier CHEBI:134607 Charge 0 Formula C56H82O2 InChIKeyhelp_outline SJOKRFJLUXNKIK-ISIUCFNPSA-N SMILEShelp_outline C1(=O)C(C)=C(C(=O)C2=CC=CC=C12)C/C=C(\C)/CCCC(C)CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline A Identifier CHEBI:13193 Charge Formula R SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 2,883 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:51924 | RHEA:51925 | RHEA:51926 | RHEA:51927 | |
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Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Partial saturation of menaquinone in Mycobacterium tuberculosis: function and essentiality of a novel reductase, MenJ.
Upadhyay A., Fontes F.L., Gonzalez-Juarrero M., McNeil M.R., Crans D.C., Jackson M., Crick D.C.
Menaquinone (MK) with partially saturated isoprenyl moieties is found in a wide range of eubacteria and Archaea. In many Gram-positive organisms, including mycobacteria, it is the double bond found in the β-isoprene unit that is reduced. Mass spectral characterization of menaquinone from mycobacte ... >> More
Menaquinone (MK) with partially saturated isoprenyl moieties is found in a wide range of eubacteria and Archaea. In many Gram-positive organisms, including mycobacteria, it is the double bond found in the β-isoprene unit that is reduced. Mass spectral characterization of menaquinone from mycobacterial knockout strains and heterologous expression hosts demonstrates that <i>Rv0561c</i> (designated <i>menJ</i>) encodes an enzyme which reduces the β-isoprene unit of menaquinone in <i>Mycobacterium tuberculosis</i>, forming the predominant form of menaquinone found in mycobacteria. MenJ is highly conserved in mycobacteria species but is not required for growth in culture. Disruption of <i>menJ</i> reduces mycobacterial electron transport efficiency by 3-fold, but mycobacteria are able to maintain ATP levels by increasing the levels of the total menaquinone in the membrane; however, MenJ is required for <i>M. tuberculosis</i> survival in host macrophages. Thus, MK with partially hydrogenated isoprenyl moieties represents a novel virulence factor and MenJ is a contextually essential enzyme and a potential drug target in pathogenic mycobacteria and other Gram-positive pathogens. << Less