ChemFOnt: Showing chemical card for Coenzyme Q10 (CFc000000846)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:21 UTC

Chemfont ID

CFc000000846

Molecule Identification

Common Name

Coenzyme Q10

Definition

Coenzyme Q10 (ubiquinone) is a naturally occurring compound widely distributed in animal organisms and in humans. The primary compounds involved in the biosynthesis of ubiquinone are 4-hydroxybenzoate and the polyprenyl chain. An essential role of coenzyme Q10 is as an electron carrier in the mitochondrial respiratory chain. Moreover, coenzyme Q10 is one of the most important lipophilic antioxidants, preventing the generation of free radicals as well as oxidative modifications of proteins, lipids, and DNA, it and can also regenerate the other powerful lipophilic antioxidant, alpha-tocopherol. Antioxidant action is a property of the reduced form of coenzyme Q10, ubiquinol (CoQ10H2), and the ubisemiquinone radical (CoQ10H*). Paradoxically, independently of the known antioxidant properties of coenzyme Q10, the ubisemiquinone radical anion (CoQ10-) possesses prooxidative properties. Decreased levels of coenzyme Q10 in humans are observed in many pathologies (e.g. cardiac disorders, neurodegenerative diseases, AIDS, cancer) associated with intensive generation of free radicals and their action on cells and tissues. In these cases, treatment involves pharmaceutical supplementation or increased consumption of coenzyme Q10 with meals as well as treatment with suitable chemical compounds (i.e. folic acid or B-group vitamins) which significantly increase ubiquinone biosynthesis in the organism. Estimation of coenzyme Q10 deficiency and efficiency of its supplementation requires a determination of ubiquinone levels in the organism. Therefore, highly selective and sensitive methods must be applied, such as HPLC with UV or coulometric detection. For a number of years, coenzyme Q (CoQ10 in humans) was known for its key role in mitochondrial bioenergetics; later studies demonstrated its presence in other subcellular fractions and in plasma, and extensively investigated its antioxidant role. These two functions constitute the basis on which research supporting the clinical use of CoQ10 is founded. Also at the inner mitochondrial membrane level, coenzyme Q is recognized as an obligatory co-factor for the function of uncoupling proteins and a modulator of the transition pore. Furthermore, recent data reveal that CoQ10 affects expression of genes involved in human cell signalling, metabolism, and transport and some of the effects of exogenously administered CoQ10 may be due to this property. Coenzyme Q is the only lipid soluble antioxidant synthesized endogenously. In its reduced form, CoQH2, ubiquinol, inhibits protein and DNA oxidation but it is the effect on lipid peroxidation that has been most deeply studied. Ubiquinol inhibits the peroxidation of cell membrane lipids and also that of lipoprotein lipids present in the circulation. Dietary supplementation with CoQ10 results in increased levels of ubiquinol-10 within circulating lipoproteins and increased resistance of human low-density lipoproteins to the initiation of lipid peroxidation. Moreover, CoQ10 has a direct anti-atherogenic effect, which has been demonstrated in apolipoprotein E-deficient mice fed with a high-fat diet. (PMID: 15928598 , 17914161 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₅₉H₉₀O₄

Average Molecular Weight

863.3435

Monoisotopic Molecular Weight

862.683911368

IUPAC Name

2-[(2E,6E,10E,14E,18E,22Z,26Z,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]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

Traditional Name

2-[(2E,6E,10E,14E,18E,22Z,26Z,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]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione

CAS Registry Number

303-98-0

SMILES

[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CCC(C)=C([H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC1=C(C)C(=O)C(OC)=C(OC)C1=O)=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30-,48-32-,49-34+,50-36+,51-38+,52-40+,53-42+

InChI Key

ACTIUHUUMQJHFO-KIEOEACUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ubiquinones. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methyl(1,4-benzoquinone) moiety to which an isoprenyl group is attached at ring position 2(or 6).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Ubiquinones

Alternative Parents

Substituents

Polyterpenoid
Polyprenylbenzoquinone
Ubiquinone skeleton
Quinone
P-benzoquinone
Vinylogous ester
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16583456)

Organ

Cell

Leukocyte (HMDB: HMDB0001072)

Tissue

Muscle tissue

Skeletal muscle (HMDB: HMDB0001072)

Excreta

Biofluid or Excreta

Feces (PMID: 23210743)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0001072)

Source

Exogenous

Exogenous (HMDB: HMDB0001072)

Endogenous

Endogenous (HMDB: HMDB0001072)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

The Oncogenic Action of Succinate (PathBank: SMP0002292)
Glutaminolysis and Cancer (PathBank: SMP0108773)
Pyruvate Dehydrogenase Deficiency (E3) (PathBank: SMP0120833)
Pyruvate Dehydrogenase Deficiency (E2) (PathBank: SMP0120834)
The Oncogenic Action of 2-Hydroxyglutarate (PathBank: SMP0002291)
Congenital Lactic Acidosis (PathBank: SMP0120610)
2-Ketoglutarate Dehydrogenase Complex Deficiency (PathBank: SMP0120832)
Fumarase Deficiency (PathBank: SMP0120611)
Mitochondrial Complex II Deficiency (PathBank: SMP0120831)
The Oncogenic Action of Fumarate (PathBank: SMP0002295)
The Oncogenic Action of L-2-Hydroxyglutarate in Hydroxygluaricaciduria (PathBank: SMP0002358)
The Oncogenic Action of D-2-Hydroxyglutarate in Hydroxygluaricaciduria (PathBank: SMP0002359)

Metabolic pathway

TCA Cycle (PathBank: SMP0002414)
Citric Acid Cycle (PathBank: SMP0063477)
Warburg Effect (PathBank: SMP0087270)
Mitochondrial Electron Transport Chain (PathBank: SMP0087354)
TCA Cycle (PathBank: SMP0002304)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00019 g/L	ALOGPS
logP	9.94	ALOGPS
logP	17.16	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	31	ChemAxon
Refractivity	286.61 m³·mol⁻¹	ChemAxon
Polarizability	110.66 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014621

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Seo, Myung-Ji; Im, Eun-Mi; Hur, Jin-Haeng; Nam, Jung-Yeon; Hyun, Chang-Gu; Pyun, Yu-Ryang; Kim, Soon-Ok. Production of coenzyme Q10 by recombinant E. coli harboring the decaprenyl diphosphate synthase gene from Sinorhizobium meliloti. Journal of Microbiology and Biotechnology (2006), 16(6), 933-938.

Showing chemical card for Coenzyme Q10 (CFc000000846)

MOL for CFc000000846 (Coenzyme Q10)

3D MOL for CFc000000846 (Coenzyme Q10)

3D SDF for CFc000000846 (Coenzyme Q10)

3D-SDF for CFc000000846 (Coenzyme Q10)

PDB for CFc000000846 (Coenzyme Q10)

3D PDB for CFc000000846 (Coenzyme Q10)

SMILES for CFc000000846 (Coenzyme Q10)

INCHI for CFc000000846 (Coenzyme Q10)

Structure for CFc000000846 (Coenzyme Q10)

3D Structure for CFc000000846 (Coenzyme Q10)