P. aeruginosa Metabolome Database: 2-methoxy-6-(all-trans-octaprenyl)phenol (PAMDB003827)

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

PAMDB003827

Identification

Name:

2-methoxy-6-(all-trans-octaprenyl)phenol

Description:

2-methoxy-6-(all-trans-octaprenyl)phenol is involved in the ubiquinol-8 biosynthesis pathway. It is a substrate for the 2-octaprenyl-6-methoxyphenol hydroxylase that catalyses the following reaction: 2-methoxy-6-(all-trans-octaprenyl)phenol + NADPH + oxygen + H+ => 2-methoxy-6-all trans-octaprenyl-2-methoxy-1,4-benzoquinol + NADP+ + H2O

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

2-Octaprenyl-6-methoxyphenol
6-methoxy-2-octaprenylphenol

Chemical Formula:

C₄₀H₅₈O₂

Average Molecular Weight:

570.8873

Monoisotopic Molecular Weight:

570.4436811

InChI Key:

CSWHQXJYVAFCED-KBSPPPJMSA-N

InChI:

InChI=1S/C40H58O2/c1-30(2)14-15-31(3)16-17-32(4)18-19-33(5)20-21-34(6)22-23-35(7)24-25-36(8)26-27-37(9)28-29-38-12-11-13-39(42-10)40(38)41/h11-14,16,18,20,22,24,26,28,41H,15,17,19,21,23,25,27,29H2,1-10H3/b31-16+,32-18+,33-20+,34-22+,35-24+,36-26+,37-28+

CAS number:

Not Available

IUPAC Name:

2-methoxy-6-[(2E,5E,8E,11E,14E,17E,20E)-3,6,9,12,15,18,21,24-octamethylpentacosa-2,5,8,11,14,17,20,23-octaen-1-yl]phenol

Traditional IUPAC Name:

2-methoxy-6-[(2E,5E,8E,11E,14E,17E,20E)-3,6,9,12,15,18,21,24-octamethylpentacosa-2,5,8,11,14,17,20,23-octaen-1-yl]phenol

SMILES:

COC1=CC=CC(C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)C\C=C(/C)CC=C(C)C)=C1O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenols and derivatives

Direct Parent

Methoxyphenols

Alternative Parents

Substituents

Methoxyphenol
Methoxybenzene
Phenol ether
Anisole
Alkyl aryl ether
Ether
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	0.00033 mg/mL	ALOGPS
logP	8.92	ALOGPS
logP	11.75	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	9.79	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	193.16 m³·mol^-1	ChemAxon
Polarizability	72.6 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-hydroxyphenol + S-adenosyl-L-methionine + 2-Octaprenyl-6-hydroxyphenol > Hydrogen ion + S-Adenosylhomocysteine + 2-methoxy-6-(all-trans-octaprenyl)phenol
Hydrogen ion + NADPH + Oxygen + 2-methoxy-6-(all-trans-octaprenyl)phenol + NADPH > Water + NADP + 2-Octaprenyl-6-methoxy-1,4-benzoquinol

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00fr-0443390000-e2611ffacd6bcc7489d9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-1955520000-784bc318b97421df8e6f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2937520000-44966b6def682f990704	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00fr-0443390000-e2611ffacd6bcc7489d9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-1955520000-784bc318b97421df8e6f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2937520000-44966b6def682f990704	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000090000-33b0abfce05062e92c9d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0000090000-28ae1f4f1bc610a02267	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zg0-0311190000-87e8ca04162634b98b69	View in MoNA

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	1235
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

• 3-demethylubiquinone-9 3-methyltransferase

General function:: Involved in 2-polyprenyl-6-methoxy-1,4-benzoquinone methyltransferase activity
Specific function:: S-adenosyl-L-methionine + 3- demethylubiquinone-9 = S-adenosyl-L-homocysteine + ubiquinone-9
Gene Name:: ubiG
Locus Tag:: PA3171
Molecular weight:: 25.9 kDa

Reactions

S-adenosyl-L-methionine + 3-demethylubiquinone-n = S-adenosyl-L-homocysteine + ubiquinone-n.
S-adenosyl-L-methionine + 3-(all-trans-polyprenyl)benzene-1,2-diol = S-adenosyl-L-homocysteine + 2-methoxy-6-(all-trans-polyprenyl)phenol.

Protein Details

• 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
Locus Tag:: PA5223
Molecular weight:: 43 kDa

2-methoxy-6-(all-trans-octaprenyl)phenol (PAMDB003827)

Structure for 2-methoxy-6-(all-trans-octaprenyl)phenol (PAMDB003827)

Enzymes

Reactions