ECMDB: 2-Octaprenyl-6-methoxy-1,4-benzoquinol (ECMDB21158) (M2MDB001567)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (2)

Record Information

Version

2.0

Creation Date

2012-07-30 14:54:43 -0600

Update Date

2015-06-03 17:20:46 -0600

Secondary Accession Numbers

ECMDB21158

Identification

Name:

2-Octaprenyl-6-methoxy-1,4-benzoquinol

Description

2-octaprenyl-6-methoxy-1,4-benzoquinol belongs to the class of Tetraterpenes. These are terpene molecules containing 10 consecutively linked isoprene units. (inferred from compound structure)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Methoxy-6-octaprenyl-2-methoxy-1,4-benzoquinol
2-Methoxy-6-[(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]benzene-1,4-diol
2-Octaprenyl-6-methoxy-1,4-benzoquinol
6-Methoxy-2-octaprenylquinol

Chemical Formula:

C₄₇H₇₂O₃

Weight:

Average: 685.0728
Monoisotopic: 684.54814617

InChI Key:

CZFRMASEEPTBAQ-MYCGWMCTSA-N

InChI:

InChI=1S/C47H72O3/c1-36(2)18-11-19-37(3)20-12-21-38(4)22-13-23-39(5)24-14-25-40(6)26-15-27-41(7)28-16-29-42(8)30-17-31-43(9)32-33-44-34-45(48)35-46(50-10)47(44)49/h18,20,22,24,26,28,30,32,34-35,48-49H,11-17,19,21,23,25,27,29,31,33H2,1-10H3/b37-20+,38-22+,39-24+,40-26+,41-28+,42-30+,43-32+

CAS number:

Not Available

IUPAC Name:

2-methoxy-6-[(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]benzene-1,4-diol

Traditional IUPAC Name:

6-methoxy-2-octaprenylquinol

SMILES:

[H]OC1=C([H])C(=C(O[H])C(OC([H])([H])[H])=C1[H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C(\[H])=C(/C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as polyprenyl quinols. Polyprenyl quinols 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

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

polyprenylhydroquinone (CHEBI:60655 )

Physical Properties

State:

Not Available

Charge:

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.00026 g/L	ALOGPS
logP	9.57	ALOGPS
logP	14.56	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	9.73	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	24	ChemAxon
Refractivity	227.34 m³·mol⁻¹	ChemAxon
Polarizability	89.19 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:

SMPDB Pathways:

Secondary Metabolites: Ubiquinol biosynthesis	PW000981
Secondary Metabolites: Ubiquinol biosynthesis 2	PW002036

KEGG Pathways:

Not Available

EcoCyc Pathways:

ubiquinol-8 biosynthesis (prokaryotic) PWY-6708

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	splash10-000i-0322129000-00e9dd4c8ebd79b2296d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a7i-1757975000-f9e82632c52857a482ee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5a-2475952000-a487a42f019ee5849295	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000009000-61a2783a089edc6cdd98	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0000009000-ab1554d5ffef09769e2b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00r2-2200039000-deb9347e6e9c23a721df	View in MoNA
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:

Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	60655
HMDB ID	Not Available
Pubchem Compound ID	49852329
Kegg ID	Not Available
ChemSpider ID	26331999
Wikipedia ID	Not Available
BioCyc ID	OCTAPRENYL-METHOXY-BENZOQUINONE
EcoCyc ID	OCTAPRENYL-METHOXY-BENZOQUINONE

Enzymes

Protein Details

1. 2-octaprenyl-6-methoxyphenol hydroxylase

General function:: Involved in oxidoreductase activity
Specific function:: Oxygenase that introduces the hydroxyl group at carbon four of 2-octaprenyl-6-methoxyphenol resulting in the formation of 2-octaprenyl-6-methoxy-1,4-benzoquinone
Gene Name:: ubiH
Uniprot ID:: P25534
Molecular weight:: 42288

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.

2-Octaprenyl-6-methoxy-1,4-benzoquinol (ECMDB21158) (M2MDB001567)

Structure for #<Compound:0xa55045ec>

Enzymes

Reactions