Showing Compound 2-Hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinol (FDB028804)

Record Information

Version

1.0

Creation date

2011-09-21 01:45:11 UTC

Update date

2015-07-21 06:59:32 UTC

Primary ID

FDB028804

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

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

Description

2-Hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinol is an ubiquinone derivative that is an intermediate in ubiquinone-6 biosynthesis. Ubiquinone (also known as coenzyme Q) is an isoprenoid quinone that functions as an electron carrier in membranes. In eukaryotes ubiquinone is found mostly within the inner mitochondrial membrane, where it functions in respiratory electron transport, transferring two electrons from either complex I (NADH dehydrogenase) or complex II (succinate-ubiquinone reductase) to complex III (bc1 complex). The quinone nucleus of ubiquinone is derived directly from 4-hydroxybenzoate , while the isoprenoid subunits of the polyisoprenoid tail are synthesized via the methylerythritol phosphate pathway , which feeds isoprene units into the Polyprenyl Biosynthesis pathways. The number of isoprenoid subunits in the ubiquinone side chain vary in different species. For example, Saccharomyces cerevisiae subsp (S288c) has 6 such subunits, Escherichia coli K-12 has 8, rat and mouse have 9, and Homo sapiens has 10. The ubiquinones are often named according to the number of carbons in the side chain or the number of isoprenoid subunits. The ubiquinone biosynthesis pathway has been elucidated primarily by the use of mutant strains that accumulate pathway intermediates. 2-Hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinol is a substrate for 5-demethoxyubiquinol hydroxylase (COQ7) and can be generated from 2-hexaprenyl-6-methoxy-1,4-benzoquinol. It is then converted by enzymatic oxidation into 2-hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol. [HMDB]

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.00034 g/L	ALOGPS
logP	8.69	ALOGPS
logP	11.75	ChemAxon
logS	-6.2	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	18	ChemAxon
Refractivity	184.78 m³·mol⁻¹	ChemAxon
Polarizability	71.27 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C38H58O3

IUPAC name

3-(3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl)-5-methoxy-2-methylbenzene-1,4-diol

InChI Identifier

InChI=1S/C38H58O3/c1-28(2)15-10-16-29(3)17-11-18-30(4)19-12-20-31(5)21-13-22-32(6)23-14-24-33(7)25-26-35-34(8)36(39)27-37(41-9)38(35)40/h15,17,19,21,23,25,27,39-40H,10-14,16,18,20,22,24,26H2,1-9H3

InChI Key

ATQQULXELMEJIX-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC(O)=C(C)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C1O

Average Molecular Weight

562.8653

Monoisotopic Molecular Weight

562.438595722

Classification

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

a 6-methoxy-3-methyl-2-<i>all-trans</i>-polyprenyl-1,4-benzoquinol (2-HEXAPRENYL-3-METHYL-6-METHOXY-14-BENZ )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
Predicted GC-MS	2-Hexaprenyl-3-methyl-6-methoxy-1,4-benzoquinol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0324090000-b5ae2a8009176d093984	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016v-0569320000-9fdad754276aa0a18050	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kb-3189410000-c62c425e34dd9a8f43c8	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000090000-9066908ab4b9c56c1133	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0000090000-4f68547cc33c50773cf1	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0072-2400590000-be63d2f0d60a0df7fd26	2015-09-15	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

30776601

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

53481382

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB12147

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB