ECMDB: 4-Hydroxy-3-polyprenylbenzoate (ECMDB23756) (M2MDB004183)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (737)

Record Information

Version

2.0

Creation Date

2015-06-04 15:13:06 -0600

Update Date

2015-08-05 16:22:04 -0600

Secondary Accession Numbers

ECMDB23756

Identification

Name:

4-Hydroxy-3-polyprenylbenzoate

Description

A member of the class of benzoates obtained by deprotonation of the carboxy group of any 4-hydroxy-3-polyprenylbenzoic acid; major species at pH 7.3

Structure

MOL SDF PDB SMILES InChI

Synonyms:

4-Hydroxy-3-polyprenylbenzoic acid

Chemical Formula:

C₁₇H₂₂O₃

Weight:

Average: 274.3548
Monoisotopic: 274.15689457

InChI Key:

HKIMBCGCVPYUTJ-NTUHNPAUSA-N

InChI:

InChI=1S/C17H22O3/c1-12(2)5-4-6-13(3)7-8-14-11-15(17(19)20)9-10-16(14)18/h5,7,9-11,18H,4,6,8H2,1-3H3,(H,19,20)/b13-7+

CAS number:

Not Available

IUPAC Name:

3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-4-hydroxybenzoic acid

Traditional IUPAC Name:

4-hydroxy-3-polyprenylbenzoate

SMILES:

CC(C)=CCC\C(C)=C\CC1=CC(=CC=C1O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Aromatic monoterpenoid
Hydroxybenzoic acid
Monocyclic monoterpenoid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:61122 )
Other Prenol lipids (C05848 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.01 g/L	ALOGPS
logP	4.32	ALOGPS
logP	4.72	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.34 m³·mol⁻¹	ChemAxon
Polarizability	31.46 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	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-Polyprenylphenol + Carbon dioxide + 4-Hydroxy-3-polyprenylbenzoate <> 4-Hydroxy-3-polyprenylbenzoate + 2-Polyprenylphenol
all-trans-Polyprenyl diphosphate + 4-Hydroxybenzoic acid + Geranyl-PP <> 4-Hydroxy-3-polyprenylbenzoate + Pyrophosphate + 4-Hydroxy-3-polyprenylbenzoate

SMPDB Pathways:

Not Available

KEGG Pathways:

Metabolic pathways eco01100
Ubiquinone and other terpenoid-quinone biosynthesis ec00130

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-8980000000-c5f21b9f2315023b8667	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0uk9-8119600000-af4084cfa0588ff40691	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0290000000-5d0c21c1fa97609e5405	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0adi-2950000000-e585e5a13ccaa004bcc8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ldi-8910000000-63c5d4612f9d7c67e790	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-7f80711f214d202e0cb3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-0090000000-aa0418550a1f9c60fa4f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0nou-3690000000-b3f087074c5c3915fcb4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-2590000000-39bbee729d92ce577091	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05ar-9800000000-aa69e3364a0f7a35d806	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-7900000000-090695f713cd5a105558	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-0090000000-b909803416c1dfda8bb5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05i0-1590000000-789b13156788008d75ed	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0900-2920000000-7363aa31358a49cf1043	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:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	61122
HMDB ID	HMDB0060388
Pubchem Compound ID	5280844
Kegg ID	C05848
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 4-hydroxybenzoate octaprenyltransferase

General function:: Involved in prenyltransferase activity
Specific function:: Synthesis of 3-octaprenyl-4-hydroxybenzoate
Gene Name:: ubiA
Uniprot ID:: P0AGK1
Molecular weight:: 32511

Reactions

4-hydroxybenzoate + farnesylfarnesylgeraniol = 3-octaprenyl-4-hydroxybenzoate.

Protein Details

2. 3-octaprenyl-4-hydroxybenzoate carboxy-lyase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of 3-octaprenyl-4-hydroxy benzoate to 2-octaprenylphenol
Gene Name:: ubiD
Uniprot ID:: P0AAB4
Molecular weight:: 55603

Protein Details

3. 3-octaprenyl-4-hydroxybenzoate carboxy-lyase

General function:: Coenzyme transport and metabolism
Specific function:: Specific function unknown
Gene Name:: ubiX
Uniprot ID:: P0AG03
Molecular weight:: 20695

4-Hydroxy-3-polyprenylbenzoate (ECMDB23756) (M2MDB004183)

Structure for #<Compound:0x54367f0>

Enzymes

Reactions