ChemFOnt: Showing chemical card for 3-Decaprenyl-4-hydroxybenzoic acid (CFc000002687)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:38 UTC

Chemfont ID

CFc000002687

Molecule Identification

Common Name

3-Decaprenyl-4-hydroxybenzoic acid

Definition

3-Decaprenyl-4-hydroxybenzoic acid is the first intermediate in the conversion of p-hydroxybenzoate (PHB) to ubiquinone. It is a 3-polyprenyl derivative of PHB. It has been found that PPHB is located primarily in the inner membrane of liver mitochondria. (PMID: 4338233 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Decaprenyl-4-hydroxybenzoate	ChEBI
PPHB-10	ChEBI
3-Decaprenyl-4-hydroxybenzoic acid	ChEBI
4-Hydroxy-3-all-trans-decaprenylbenzoate	Generator, HMDB

Chemical Formula

C₅₇H₈₆O₃

Average Molecular Weight

819.2909

Monoisotopic Molecular Weight

818.657696618

IUPAC Name

3-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-4-hydroxybenzoic acid

Traditional Name

pphb-10

CAS Registry Number

636-57-7

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C=CC(=C1)C(O)=O

InChI Identifier

InChI=1S/C57H86O3/c1-44(2)21-12-22-45(3)23-13-24-46(4)25-14-26-47(5)27-15-28-48(6)29-16-30-49(7)31-17-32-50(8)33-18-34-51(9)35-19-36-52(10)37-20-38-53(11)39-40-54-43-55(57(59)60)41-42-56(54)58/h21,23,25,27,29,31,33,35,37,39,41-43,58H,12-20,22,24,26,28,30,32,34,36,38,40H2,1-11H3,(H,59,60)/b45-23+,46-25+,47-27+,48-29+,49-31+,50-33+,51-35+,52-37+,53-39+

InChI Key

CMPNJZREBHCPHN-LTNIBBDRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as polyprenylphenols. Polyprenylphenols are compounds containing a polyisoprene chain attached to a phenol group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenylphenols

Direct Parent

Polyprenylphenols

Alternative Parents

Substituents

Polyterpenoid
Polyprenylphenol
Hydroxybenzoic acid
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
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

olefinic compound (CHEBI:64136 )
monohydroxybenzoic acid (CHEBI:64136 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0006251)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006251)

Source

Endogenous

Endogenous (HMDB: HMDB0006251)

Animal

Animal (HMDB: HMDB0006251)

Exogenous

Food

Food (HMDB: HMDB0006251)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0006251)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006251)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006251)

Lipid metabolism pathway (HMDB: HMDB0006251)

Cellular process

Cell signaling (HMDB: HMDB0006251)

Biochemical process

Lipid transport (HMDB: HMDB0006251)

Role

Biological role

Energy source (HMDB: HMDB0006251)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006251)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00023 g/L	ALOGPS
logP	9.96	ALOGPS
logP	17.99	ChemAxon
logS	-6.6	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	30	ChemAxon
Refractivity	273.76 m³·mol⁻¹	ChemAxon
Polarizability	107.7 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

External Links

HMDB ID

HMDB0006251

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023861

KNApSAcK ID

Not Available

Chemspider ID

4956995

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2266634

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6454686

PDB ID

Not Available

ChEBI ID

64136

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-Decaprenyl-4-hydroxybenzoic acid (CFc000002687)

MOL for CFc000002687 (3-Decaprenyl-4-hydroxybenzoic acid)

3D MOL for CFc000002687 (3-Decaprenyl-4-hydroxybenzoic acid)

3D SDF for CFc000002687 (3-Decaprenyl-4-hydroxybenzoic acid)

3D-SDF for CFc000002687 (3-Decaprenyl-4-hydroxybenzoic acid)

PDB for CFc000002687 (3-Decaprenyl-4-hydroxybenzoic acid)

3D PDB for CFc000002687 (3-Decaprenyl-4-hydroxybenzoic acid)

SMILES for CFc000002687 (3-Decaprenyl-4-hydroxybenzoic acid)

INCHI for CFc000002687 (3-Decaprenyl-4-hydroxybenzoic acid)

Structure for CFc000002687 (3-Decaprenyl-4-hydroxybenzoic acid)

3D Structure for CFc000002687 (3-Decaprenyl-4-hydroxybenzoic acid)