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Record Information

Version

2.0

Creation Date

2012-10-22 13:35:01 -0600

Update Date

2015-06-03 17:26:44 -0600

Secondary Accession Numbers

ECMDB23436

Identification

Name:

6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol

Description

6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol is involved in the ubiquinol-8 biosynthesis pathway. It is a substrate of 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinone hydroxylase that catalyses the following reaction: 6-methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol + a reduced electron acceptor + oxygen => 3-demethylubiquinol-8 + an oxidized electron acceptor + H2O

Structure

MOL SDF PDB SMILES InChI

Synonyms:

Not Available

Chemical Formula:

C₄₆H₇₀O₃

Weight:

Average: 671.0462
Monoisotopic: 670.532496106

InChI Key:

CRUUXCIHJFUTIZ-WZVGXJGASA-N

InChI:

InChI=1S/C46H70O3/c1-34(2)27-28-41(9)30-29-39(7)25-15-23-37(5)21-13-19-35(3)17-12-18-36(4)20-14-22-38(6)24-16-26-40(8)31-32-43-42(10)44(47)33-45(49-11)46(43)48/h17,20-21,24-25,27,30-31,33,47-48H,12-16,18-19,22-23,26,28-29,32H2,1-11H3/b35-17+,36-20+,37-21+,38-24+,39-25+,40-31+,41-30+

CAS number:

Not Available

IUPAC Name:

5-methoxy-2-methyl-3-[(2E,6E,10E,14E,18E,22E,25E)-3,7,11,15,19,23,26,29-octamethyltriaconta-2,6,10,14,18,22,25,28-octaen-1-yl]benzene-1,4-diol

Traditional IUPAC Name:

5-methoxy-2-methyl-3-[(2E,6E,10E,14E,18E,22E,25E)-3,7,11,15,19,23,26,29-octamethyltriaconta-2,6,10,14,18,22,25,28-octaen-1-yl]benzene-1,4-diol

SMILES:

COC1=C(O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C\C=C(/C)CC=C(C)C)=C(C)C(O)=C1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. 2-polyprenyl-6-methoxyphenols are compounds containing a polyisoprene chain attached at the 2-position of a 6-methoxyphenol group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenylphenols

Direct Parent

2-polyprenyl-6-methoxyphenols

Alternative Parents

Substituents

2-polyprenyl-6-methoxyphenol
Polyprenylbenzoquinol
Sesterterpenoid
Prenylbenzoquinol
Methoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
O-cresol
M-cresol
Hydroquinone
Anisole
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	0.00028 g/L	ALOGPS
logP	9.24	ALOGPS
logP	14.18	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	9.98	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	223.18 m³·mol⁻¹	ChemAxon
Polarizability	85.91 Å³	ChemAxon
Number of Rings	1	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:

2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-adenosyl-L-methionine > S-Adenosylhomocysteine + Hydrogen ion + 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol
Oxygen + Reduced acceptor + 6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol > Water + oxidized electron acceptor + 3-demethylubiquinol-8

SMPDB Pathways:

Secondary Metabolites: Ubiquinol biosynthesis

PW000981

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0221229000-fc661d3ce4b8ec708206	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-0697784000-61ea24af909b8f4eaeaa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1299-0497741000-99e4dc3be0546c0018d9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000009000-7ec3740028f154d9651f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0000009000-30798e5bd8328f980a0d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f79-2400079000-a2f5bffa69a3a8b673c0	View in MoNA
MS	Mass Spectrum (Electron Ionization)	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol hydroxylase

General function:: Involved in oxidoreductase activity
Specific function:: Oxygenase that introduces the hydroxyl group at carbon five of 2-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol resulting in the formation of 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4- benzoquinol
Gene Name:: ubiF
Uniprot ID:: P75728
Molecular weight:: 42953

Protein Details

2. Ubiquinone/menaquinone biosynthesis methyltransferase ubiE

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.

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6-Methoxy-3-methyl-2-all-trans-octaprenyl-1,4-benzoquinol (M2MDB003826)

Structure for #<Compound:0xa8a3a0a4>

Enzymes

Reactions