Record Information
Version2.0
Creation Date2012-07-30 14:54:42 -0600
Update Date2015-06-03 17:20:46 -0600
Secondary Accession Numbers
  • ECMDB21155
Identification
Name:2-Demethylmenaquinone 8
Description:2-demethylmenaquinone 8 belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure)
Structure
Thumb
Synonyms:
  • 2-demethylmenaquinone 8
  • Demethylmenaquinone
  • DMK-8
Chemical Formula:C50H70O2
Weight:Average: 703.0896
Monoisotopic: 702.537581484
InChI Key:GDUBPWSFXUAETN-AENDIINCSA-N
InChI:InChI=1S/C50H70O2/c1-38(2)19-12-20-39(3)21-13-22-40(4)23-14-24-41(5)25-15-26-42(6)27-16-28-43(7)29-17-30-44(8)31-18-32-45(9)35-36-46-37-49(51)47-33-10-11-34-48(47)50(46)52/h10-11,19,21,23,25,27,29,31,33-35,37H,12-18,20,22,24,26,28,30,32,36H2,1-9H3/b39-21+,40-23+,41-25+,42-27+,43-29+,44-31+,45-35+
CAS number:Not Available
IUPAC Name:2-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-yl]-1,4-dihydronaphthalene-1,4-dione
Traditional IUPAC Name:demethylmenaquinone
SMILES:[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=CC(=O)C2=CC=CC=C2C1=O)=C(\C)CCC=C(C)C
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as tetraterpenoids. These are terpenoid molecules containing 10 consecutively linked isoprene units.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentTetraterpenoids
Alternative Parents
Substituents
  • Tetraterpenoid
  • Menaquinone
  • Naphthoquinone
  • Naphthalene
  • Aryl ketone
  • Quinone
  • Benzenoid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.000202 mg/mLALOGPS
logP10.02ALOGPS
logP14.72ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)12.48ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count23ChemAxon
Refractivity236.36 m3·mol-1ChemAxon
Polarizability90.34 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:
Menaquinol biosythesisPW001897 Pw001897Pw001897 greyscalePw001897 simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0323238900-c1cf779f996405bed20eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kcs-0426591000-f3dcc006b4aab412fcdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-100r-1225591000-3dd566bd125705c2fe7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000900-32834522502b0efa06b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0100002900-ddf9f8fd8f34480c9d8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-1611139000-116bcc6bbe7a44846bccView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID48455
HMDB IDNot Available
Pubchem Compound ID5376004
Kegg IDC05818
ChemSpider ID4525368
Wikipedia IDNot Available
BioCyc IDDEMETHYLMENAQUINONE
EcoCyc IDDEMETHYLMENAQUINONE

Enzymes

General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
frdA
Uniprot ID:
P00363
Molecular weight:
65971
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in oxidation-reduction process
Specific function:
Transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone. Does not couple the redox reaction to proton translocation
Gene Name:
ndh
Uniprot ID:
P00393
Molecular weight:
47358
Reactions
NADH + acceptor = NAD(+) + reduced acceptor.
General function:
Energy production and conversion
Specific function:
Seems to be involved in the anchoring of the catalytic components of the fumarate reductase complex to the cytoplasmic membrane
Gene Name:
frdC
Uniprot ID:
P0A8Q0
Molecular weight:
15015
General function:
Involved in fumarate metabolic process
Specific function:
Seems to be involved in the anchoring of the catalytic components of the fumarate reductase complex to the cytoplasmic membrane
Gene Name:
frdD
Uniprot ID:
P0A8Q3
Molecular weight:
13107
General function:
Involved in iron-sulfur cluster binding
Specific function:
Electron transfer protein; may also function as the membrane anchor for the glpAB dimer
Gene Name:
glpC
Uniprot ID:
P0A996
Molecular weight:
44108
General function:
Involved in oxidoreductase activity
Specific function:
Conversion of glycerol 3-phosphate to dihydroxyacetone. Uses fumarate or nitrate as electron acceptor
Gene Name:
glpA
Uniprot ID:
P0A9C0
Molecular weight:
58958
Reactions
sn-glycerol 3-phosphate + a quinone = glycerone phosphate + a quinol.
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
frdB
Uniprot ID:
P0AC47
Molecular weight:
27123
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in nickel cation binding
Specific function:
This is one of three E.coli hydrogenases synthesized in response to different physiological conditions. HYD1 is believed to have a role in hydrogen cycling during fermentative growth
Gene Name:
hyaB
Uniprot ID:
P0ACD8
Molecular weight:
66253
Reactions
H(2) + A = AH(2).
General function:
Involved in nickel cation binding
Specific function:
This is one of three E.coli hydrogenases synthesized in response to different physiological conditions. HYD2 is involved in hydrogen uptake
Gene Name:
hybC
Uniprot ID:
P0ACE0
Molecular weight:
62491
Reactions
H(2) + A = AH(2).
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
glcD
Uniprot ID:
P0AEP9
Molecular weight:
53811
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoA
Uniprot ID:
P0AFC3
Molecular weight:
16457
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoB
Uniprot ID:
P0AFC7
Molecular weight:
25056
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidoreductase activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoE
Uniprot ID:
P0AFD1
Molecular weight:
18590
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidation-reduction process
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient. This subunit may bind ubiquinone
Gene Name:
nuoH
Uniprot ID:
P0AFD4
Molecular weight:
36219
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in electron carrier activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoI
Uniprot ID:
P0AFD6
Molecular weight:
20538
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoJ
Uniprot ID:
P0AFE0
Molecular weight:
19874
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
There are 2 NADH dehydrogenases in E.coli, however only this complex is able to use dNADH (reduced nicotinamide hypoxanthine dinucleotide, deamino-NADH) and dNADH-DB (dimethoxy- 5-methyl-6-decyl-1,4-benzoquinone) as substrates
Gene Name:
nuoK
Uniprot ID:
P0AFE4
Molecular weight:
10845
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoM
Uniprot ID:
P0AFE8
Molecular weight:
56524
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoN
Uniprot ID:
P0AFF0
Molecular weight:
52044
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in electron carrier activity
Specific function:
Conversion of glycerol 3-phosphate to dihydroxyacetone. Uses fumarate or nitrate as electron acceptor
Gene Name:
glpB
Uniprot ID:
P13033
Molecular weight:
45357
Reactions
sn-glycerol 3-phosphate + a quinone = glycerone phosphate + a quinol.
General function:
Involved in dimethyl sulfoxide reductase activity
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. Allows E.coli to grow anaerobically on Me(2)SO as respiratory oxidant
Gene Name:
dmsA
Uniprot ID:
P18775
Molecular weight:
90398
Reactions
Dimethylsulfide + menaquinone + H(2)O = dimethylsulfoxide + menaquinol.
General function:
Involved in electron carrier activity
Specific function:
Electron transfer subunit of the terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds
Gene Name:
dmsB
Uniprot ID:
P18776
Molecular weight:
22869
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoF
Uniprot ID:
P31979
Molecular weight:
49292
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in transferase activity
Specific function:
Conversion of 1,4-dihydroxy-2-naphthoate (DHNA) to dimethylmenaquinone (DMK). Attaches octaprenylpyrophosphate, a membrane-bound 40-carbon side chain to DHNA. The conversion of DHNA to DMK proceeds in three stages:the removal of the carboxyl group of DHNA as CO(2), the attachment of the isoprenoid side chain, and a quinol-to-quinone oxidation, which is thought to be spontaneous
Gene Name:
menA
Uniprot ID:
P32166
Molecular weight:
33594
Reactions
An all-trans-polyprenyl diphosphate + 1,4-dihydroxy-2-naphthoate = a demethylmenaquinol + diphosphate + CO(2).
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoC
Uniprot ID:
P33599
Molecular weight:
68236
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in electron carrier activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoG
Uniprot ID:
P33602
Molecular weight:
100298
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
NDH-1 shuttles electrons from NADH, via FMN and iron- sulfur (Fe-S) centers, to quinones in the respiratory chain. The immediate electron acceptor for the enzyme in this species is believed to be ubiquinone. Couples the redox reaction to proton translocation (for every two electrons transferred, four hydrogen ions are translocated across the cytoplasmic membrane), and thus conserves the redox energy in a proton gradient
Gene Name:
nuoL
Uniprot ID:
P33607
Molecular weight:
66438
Reactions
NADH + quinone = NAD(+) + quinol.
General function:
Involved in iron-sulfur cluster binding
Specific function:
Specific function unknown
Gene Name:
glcF
Uniprot ID:
P52074
Molecular weight:
45110
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
This is one of three E.coli hydrogenases synthesized in response to different physiological conditions. HYD1 is believed to have a role in hydrogen cycling during fermentative growth
Gene Name:
hyaA
Uniprot ID:
P69739
Molecular weight:
40681
Reactions
H(2) + A = AH(2).
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
This is one of three E.coli hydrogenases synthesized in response to different physiological conditions. HYD2 is involved in hydrogen uptake
Gene Name:
hybO
Uniprot ID:
P69741
Molecular weight:
39652
Reactions
H(2) + A = AH(2).
General function:
Involved in oxidoreductase activity
Specific function:
Reduces trimethylamine-N-oxide (TMAO) into trimethylamine; an anaerobic reaction coupled to energy-yielding reactions. Can also reduce other N- and S-oxide compounds such as 4-methylmorpholine-N-oxide and biotin sulfoxide (BSO), but with a lower catalytic efficiency
Gene Name:
torZ
Uniprot ID:
P46923
Molecular weight:
88964
Reactions
Trimethylamine + 2 (ferricytochrome c)-subunit + H(2)O = trimethylamine N-oxide + 2 (ferrocytochrome c)-subunit + 2 H(+).
General function:
Involved in coenzyme binding
Specific function:
Specific function unknown
Gene Name:
mdaB
Uniprot ID:
P0AEY5
Molecular weight:
21891
General function:
Involved in iron ion binding
Specific function:
Part of the anaerobic respiratory chain of trimethylamine-N-oxide reductase torZ. Required for electron transfer to the torZ terminal enzyme
Gene Name:
torY
Uniprot ID:
P52005
Molecular weight:
40286
General function:
Involved in anaerobic electron transport chain
Specific function:
Terminal reductase during anaerobic growth on various sulfoxide and N-oxide compounds. DmsC anchors the dmsAB dimer to the membrane and stabilizes it
Gene Name:
dmsC
Uniprot ID:
P18777
Molecular weight:
30826
General function:
Involved in electron carrier activity
Specific function:
Probable b-type cytochrome
Gene Name:
hyaC
Uniprot ID:
P0AAM1
Molecular weight:
27597
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
glcE
Uniprot ID:
P52073
Molecular weight:
38361
General function:
Involved in electron carrier activity
Specific function:
Participates in the periplasmic electron-transferring activity of hydrogenase 2 during its catalytic turnover
Gene Name:
hybA
Uniprot ID:
P0AAJ8
Molecular weight:
36003
General function:
Involved in oxidoreductase activity
Specific function:
Reduces trimethylamine-N-oxide (TMAO) into trimethylamine; an anaerobic reaction coupled to energy-yielding reactions
Gene Name:
torA
Uniprot ID:
P33225
Molecular weight:
94455
Reactions
Trimethylamine + 2 (ferricytochrome c)-subunit + H(2)O = trimethylamine N-oxide + 2 (ferrocytochrome c)-subunit + 2 H(+).
General function:
Involved in metal ion binding
Specific function:
Probable b-type cytochrome
Gene Name:
hybB
Uniprot ID:
P37180
Molecular weight:
43602
General function:
Involved in iron ion binding
Specific function:
Part of the anaerobic respiratory chain of trimethylamine-N-oxide reductase torA. Acts by transferring electrons from the membranous menaquinones to torA. This transfer probably involves an electron transfer pathway from menaquinones to the N-terminal domain of torC, then from the N-terminus to the C-terminus, and finally to torA. TorC apocytochrome negatively autoregulates the torCAD operon probably by inhibiting the torS kinase activity
Gene Name:
torC
Uniprot ID:
P33226
Molecular weight:
43606
General function:
Involved in methyltransferase activity
Specific function:
Methyltransferase required for the conversion of dimethylmenaquinone (DMKH2) to menaquinone (MKH2) and the conversion of 2-polyprenyl-6-methoxy-1,4-benzoquinol (DDMQH2) to 2-polyprenyl-3-methyl-6-methoxy-1,4-benzoquinol (DMQH2)
Gene Name:
ubiE
Uniprot ID:
P0A887
Molecular weight:
28073
Reactions
A demethylmenaquinone + S-adenosyl-L-methionine = a menaquinol + S-adenosyl-L-homocysteine.
S-adenosyl-L-methionine + 2-methoxy-6-all-trans-polyprenyl-1,4-benzoquinol = S-adenosyl-L-homocysteine + 6-methoxy-3-methyl-2-all-trans-polyprenyl-1,4-benzoquinol.