ECMDB: 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol (ECMDB21157) (M2MDB001566)

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 14:54:42 -0600

Update Date

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

Secondary Accession Numbers

ECMDB21157

Identification

Name:

2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol

Description

2-octaprenyl-3-methyl-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-octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol
2Oct3Me6Meth1,4BQ
6-Methoxy-3-methyl-2-octaprenyl-1,4-benzoquinol

Chemical Formula:

C₄₈H₇₆O₃

Weight:

Average: 701.1152
Monoisotopic: 700.579446298

InChI Key:

GCGITSVDDBZRNB-KFSSTAEESA-N

InChI:

InChI=1S/C48H76O3/c1-36(2)19-12-20-37(3)21-13-22-38(4)23-14-24-39(5)25-15-26-40(6)27-16-28-41(7)29-17-30-42(8)31-18-32-43(9)33-34-45-44(10)46(49)35-47(51-11)48(45)50/h19,21,23,25,27,29,31,33,35,46,48-50H,12-18,20,22,24,26,28,30,32,34H2,1-11H3/b37-21+,38-23+,39-25+,40-27+,41-29+,42-31+,43-33+

CAS number:

Not Available

IUPAC Name:

5-methoxy-2-methyl-3-[(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]cyclohexa-2,5-diene-1,4-diol

Traditional IUPAC Name:

5-methoxy-2-methyl-3-[(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]cyclohexa-2,5-diene-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])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(C)C(O)C=C(OC)C1O)=C(\C)CCC=C(C)C

Chemical Taxonomy

Description

belongs to the class of organic compounds known as polyterpenoids. These are terpenoids consisting of more than eight isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyterpenoids

Direct Parent

Polyterpenoids

Alternative Parents

Substituents

Polyterpenoid
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic 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	0.00035 g/L	ALOGPS
logP	8.72	ALOGPS
logP	12.56	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	-3.2	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	233.59 m³·mol⁻¹	ChemAxon
Polarizability	90.99 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-3-methyl-6-methoxy-1,4-benzoquinol + Oxygen > 2-Octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol
2-Octaprenyl-6-methoxy-1,4-benzoquinol + S-Adenosylmethionine > 2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + S-Adenosylhomocysteine + Hydrogen ion
2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol + Oxygen + a reduced electron acceptor > 2-octaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinone + Water + an oxidized electron acceptor

SMPDB Pathways:

Not Available

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_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-0201129300-b370fd90c550be15594d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0935473000-8b2674a6e3a93817872d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kaj-1888791000-94ff8725c06c7e8da687	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000009000-d448fee2cccb2ff33d80	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000t-0000009000-92cbfd128078572fcb92	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-2000019000-b0c83fb8fbb6ae19b855	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	60656
HMDB ID	Not Available
Pubchem Compound ID	49852330
Kegg ID	C05814
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	OCTAPRENYL-METHYL-METHOXY-BENZQ
EcoCyc ID	OCTAPRENYL-METHYL-METHOXY-BENZQ

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.

2-Octaprenyl-3-methyl-6-methoxy-1,4-benzoquinol (ECMDB21157) (M2MDB001566)

Structure for #<Compound:0x3b3b0d68>

Enzymes

Reactions