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Details

Stereochemistry ACHIRAL
Molecular Formula C19H26O4
Molecular Weight 318.4073
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of UBIQUINONE Q2

SMILES

COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O

InChI

InChIKey=SQQWBSBBCSFQGC-JLHYYAGUSA-N
InChI=1S/C19H26O4/c1-12(2)8-7-9-13(3)10-11-15-14(4)16(20)18(22-5)19(23-6)17(15)21/h8,10H,7,9,11H2,1-6H3/b13-10+

HIDE SMILES / InChI

Molecular Formula C19H26O4
Molecular Weight 318.4073
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Ubiquinone Q2 (CoQ(2)) is a member of the chemical class known as Polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Ubiquione-2 has just 2 isoprene units. Normally in humans it has 10. Ubiquinone-2 is an intermediate in the synthesis of Ubiquionone 10. Ubiquionone is involved in cellular respiration. It is fat-soluble and is therefore mobile in cellular membranes; it plays a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP. The first ubiquinone was isolated in 1957. Since that time, ubiquinones have been extensively studied in Japan, Russia, and Europe with research in the US beginning more recently. Popular press accounts claim that roughly 12 million Japanese use ubiquinones as the medication of choice for management of cardiovascular diseases, with more than 250 commercially available preparations. Ubiquinone is touted as an effective treatment of congestive heart failure (CHF), heart rhythm irregularities, high blood pressure, and in reducing injury to the heart muscle caused by lack of oxygen. Other claims include increasing exercise tolerance, stimulating the immune system, and counteracting the aging process. Ubiquinone has not been approved for therapeutic use in the US, but it is available as a food supplement. Ubiquinone may have applications in heart disease, especially CHF, although there is a lack of consensus. Studies in neurological disorders are less promising. Limited clinical trials have been conducted to support its widespread use for other conditions.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Mitochondrial complex I encephalomyopathy and cerebral 5-methyltetrahydrofolate deficiency.
2007 Aug
Old and new inhibitors of quinone reductase 2.
2010 Jul 30
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: Coenzymes Q1 to Q3 inhibited the growth and to a greater extent exotoxin production of Staphylococcus aureus, Bacillus anthracis, Streptococcus pyogenes, and Streptococcus agalactiae at concentrations of 10 to 200 ug/ml. https://www.ncbi.nlm.nih.gov/pubmed/23959313
Ubiquinone Q2 (23 uM) reduced the respiratory control index by 32% and 57% (p<0.01) in heart and liver mitochondria respectively, mainly through an increased oxygen consumption in state. Addition of CoQ2 significantly decreased specific NADH DUb-reductase activity in both mitochondria averaging 196±15 nmol/min/mg prot in heart mitonchondria (p<0.05 vs control) and 20± 2 nmol/min/mg prot in liver mitochondria (p<0.05 vs control)
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:37:49 UTC 2023
Edited
by admin
on Fri Dec 15 19:37:49 UTC 2023
Record UNII
I7T5V2W47R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UBIQUINONE Q2
Common Name English
UBIQUINONE 2
Common Name English
2,3-DIMETHOXY-5-GERANYL-6-METHYL-1,4-BENZOQUINONE
Systematic Name English
Q 2
Common Name English
2,5-CYCLOHEXADIENE-1,4-DIONE, 2-((2E)-3,7-DIMETHYL-2,6-OCTADIEN-1-YL)-5,6-DIMETHOXY-3-METHYL-
Systematic Name English
COENZYME Q2
Common Name English
P-BENZOQUINONE, 2-GERANYL-5,6-DIMETHOXY-3-METHYL-
Common Name English
Code System Code Type Description
FDA UNII
I7T5V2W47R
Created by admin on Fri Dec 15 19:37:49 UTC 2023 , Edited by admin on Fri Dec 15 19:37:49 UTC 2023
PRIMARY
RXCUI
1423925
Created by admin on Fri Dec 15 19:37:49 UTC 2023 , Edited by admin on Fri Dec 15 19:37:49 UTC 2023
PRIMARY RxNorm
CAS
606-06-4
Created by admin on Fri Dec 15 19:37:49 UTC 2023 , Edited by admin on Fri Dec 15 19:37:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID001019698
Created by admin on Fri Dec 15 19:37:49 UTC 2023 , Edited by admin on Fri Dec 15 19:37:49 UTC 2023
PRIMARY
DAILYMED
I7T5V2W47R
Created by admin on Fri Dec 15 19:37:49 UTC 2023 , Edited by admin on Fri Dec 15 19:37:49 UTC 2023
PRIMARY
DRUG BANK
DB08690
Created by admin on Fri Dec 15 19:37:49 UTC 2023 , Edited by admin on Fri Dec 15 19:37:49 UTC 2023
PRIMARY
PUBCHEM
5280346
Created by admin on Fri Dec 15 19:37:49 UTC 2023 , Edited by admin on Fri Dec 15 19:37:49 UTC 2023
PRIMARY