P. aeruginosa Metabolome Database: 2-Octaprenyl-6-methoxy-1,4-benzoquinol (PAMDB001567)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001567

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 View Structure

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

Average Molecular Weight:

685.0728

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound belongs to the class of organic compounds known as 2-polyprenyl-6-methoxyphenols. These 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
Prenylbenzoquinol
Methoxyphenol
Hydroxyquinol derivative
Methoxybenzene
Phenol ether
Hydroquinone
Anisole
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Ether
Hydrocarbon derivative
Organooxygen compound
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	0.000261 mg/mL	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:

2-Octaprenyl-6-methoxyphenol + Oxygen > 2-Octaprenyl-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-6-methoxyphenol + Oxygen + NADPH + Hydrogen ion > 2-Octaprenyl-6-methoxy-1,4-benzoquinol + Water + NADP
Hydrogen ion + NADPH + Oxygen + 2-methoxy-6-(all-trans-octaprenyl)phenol + NADPH > Water + NADP + 2-Octaprenyl-6-methoxy-1,4-benzoquinol
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

Pathways:

Not Available

Spectra

Spectra:

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

2-Octaprenyl-6-methoxy-1,4-benzoquinol (PAMDB001567)

Structure for 2-Octaprenyl-6-methoxy-1,4-benzoquinol (PAMDB001567)