P. aeruginosa Metabolome Database: Menaquinol 6 (PAMDB001946)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB001946

Identification

Name:

Menaquinol 6

Description:

Menaquinol 6 is a polyprenylhydroquinone having a hexaprenyl moiety at position 2 and a methyl group at position 3. It is a substrate for Dimethyl sulfoxide reductase (dmsA). This enzyme catalyzes the reduction of dimethyl sulfoxide (DMSO) to dimethyl sulfide (DMS) using the following reaction: Dimethylsulfide + menaquinone + H2O = dimethylsulfoxide + menaquinol. DMSO reductase serves as the terminal reductase under anaerobic conditions, with DMSO being the terminal electron acceptor. Terminal reductase during anaerobic growth on various sulfoxides and N-oxide compounds. This enzyme allows P. aeruginosa to grow anaerobically on DMSO as respiratory oxidant. Menaquinol 6 is generated by Ubiquinone/menaquinone biosynthesis methyltransferase (ubiE). This enzyme is required for the conversion of demethylmenaquinone (DMKH2) to menaquinone (MKH2) and has the following catalytic activity: A demethylmenaquinone + S-adenosyl-L-methionine = a menaquinol + S-adenosyl-L-homocysteine.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

A Menaquinol
Menaquinol
Reduced menaquinone
Reduced vitamin K2
Vitamin K2 hydroquinone

Chemical Formula:

C₄₁H₅₈O₂

Average Molecular Weight:

582.898

Monoisotopic Molecular Weight:

582.4436811

InChI Key:

ZVENTDGZQVBWNA-RCIYGOBDSA-N

InChI:

InChI=1S/C41H58O2/c1-30(2)16-11-17-31(3)18-12-19-32(4)20-13-21-33(5)22-14-23-34(6)24-15-25-35(7)28-29-37-36(8)40(42)38-26-9-10-27-39(38)41(37)43/h9-10,16,18,20,22,24,26-28,42-43H,11-15,17,19,21,23,25,29H2,1-8H3/b31-18+,32-20+,33-22+,34-24+,35-28+

CAS number:

39776-48-2

IUPAC Name:

2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methylnaphthalene-1,4-diol

Traditional IUPAC Name:

2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-3-methylnaphthalene-1,4-diol

SMILES:

[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(O)C2=CC=CC=C2C(O)=C1C)=C(\C)CCC=C(C)C

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as polyprenyl quinols. These are compounds containing a polyisoprene chain attached to a quinol(hydroquinone) at the second ring position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Polyprenyl quinols

Alternative Parents

Substituents

Polyprenylbenzoquinol
Polyprenylphenol
Sesterterpenoid
1-naphthol
Naphthalene
Hydroquinone
Benzenoid
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.000276 mg/mL	ALOGPS
logP	9.29	ALOGPS
logP	12.9	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	9.38	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	194.77 m³·mol^-1	ChemAxon
Polarizability	74.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Membrane

Reactions:

Protoporphyrinogen IX + 3 Menaquinone + 3 Menaquinone <> Protoporphyrin IX +3 Menaquinol 6
Demethylmenaquinol + S-Adenosylmethionine + Demethylmenaquinol <> Menaquinol 6 + S-Adenosylhomocysteine
Dimethyl sulfide + Menaquinone + Water > Dimethyl sulfoxide + Menaquinol 6
Protoporphyrinogen IX + 3 Menaquinone > Protoporphyrin IX +3 Menaquinol 6
Menaquinone + Water + Dimethyl sulfide <> Menaquinol 6
Protoporphyrinogen IX + menaquinone-8 > Protoporphyrin IX + Menaquinol 6

Pathways:

Metabolic pathways pae01100
Porphyrin and chlorophyll metabolism pae00860
Sulfur metabolism pae00920
Ubiquinone and other terpenoid-quinone biosynthesis pae00130

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0223090000-23a445bdcbe0768e162d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-054y-0549220000-1badad58095ed0f65fae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k92-2159410000-e96cf420729fd4eb7066	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000090000-e521a6b39bcfc988308d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0100090000-c01fde52bc298d1c3773	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01b9-1703190000-697d8ca95a75ab4e5b61	View in MoNA

References

References:

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." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	18151
HMDB ID	Not Available
Pubchem Compound ID	6441040
Kegg ID	C05819
ChemSpider ID	4945264
Wikipedia ID	Not Available
BioCyc ID	Not Available

Menaquinol 6 (PAMDB001946)

Structure for Menaquinol 6 (PAMDB001946)