ChemFOnt: Showing chemical card for 3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid (CFc000000777)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:16 UTC

Chemfont ID

CFc000000777

Molecule Identification

Common Name

3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid

Definition

3-Hexaprenyl-4-hydroxy-5-methoxybenzoic acid is an intermediate in the biosynthesis of Ubiquinone. It is a substrate for Hexaprenyldihydroxybenzoate methyltransferase (mitochondrial).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Hexaprenyl-4-hydroxy-5-methoxybenzoate	ChEBI
3-Methoxy-4-hydroxy-5-hexaprenylbenzoate	HMDB
3-Methoxy-4-hydroxy-5-hexaprenylbenzoic acid	HMDB, MeSH
3-MHHB	HMDB, MeSH
Hexaprenyl-4-hydroxy-5-methoxybenzoate	HMDB
Hexaprenyl-4-hydroxy-5-methoxybenzoic acid	HMDB

Chemical Formula

C₃₈H₅₆O₄

Average Molecular Weight

576.8488

Monoisotopic Molecular Weight

576.41786028

IUPAC Name

3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4-hydroxy-5-methoxybenzoic acid

Traditional Name

3-mhhb

CAS Registry Number

66551-60-8

SMILES

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

InChI Identifier

InChI=1S/C38H56O4/c1-28(2)14-9-15-29(3)16-10-17-30(4)18-11-19-31(5)20-12-21-32(6)22-13-23-33(7)24-25-34-26-35(38(40)41)27-36(42-8)37(34)39/h14,16,18,20,22,24,26-27,39H,9-13,15,17,19,21,23,25H2,1-8H3,(H,40,41)/b29-16+,30-18+,31-20+,32-22+,33-24+

InChI Key

YSZSVGFMAJXGMQ-FRICUITQSA-N

Chemical Taxonomy

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
Sesterterpenoid
M-methoxybenzoic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Benzoic acid or derivatives
Benzoic acid
Methoxybenzene
Benzoyl
Phenoxy compound
Anisole
Phenol ether
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:16835 )
methoxybenzoic acid (CHEBI:16835 )
Ubiquinones (LMPR02010044 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000977)

Source

Endogenous

Endogenous (HMDB: HMDB0000977)

Animal

Animal (HMDB: HMDB0000977)

Exogenous

Food

Food (HMDB: HMDB0000977)

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: HMDB0000977)

Process

Role

Biological role

Energy source (HMDB: HMDB0000977)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000977)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00036 g/L	ALOGPS
logP	8.61	ALOGPS
logP	11.2	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	4.12	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	185.01 m³·mol⁻¹	ChemAxon
Polarizability	72.35 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