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Showing metabocard for Ubiquinone-4 (HMDB06710)

Record Information
Version 3.5
Creation Date 2007-07-11 03:24:51 -0600
Update Date 2013-02-08 17:15:11 -0700
HMDB ID HMDB06710
Secondary Accession Numbers None
Metabolite Identification
Common Name Ubiquinone-4
Description Ubiquinone-4 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-4 has just 4 isoprene units. Normally in humans it has 10 (CoQ10). Ubiquinone-4 is an intermediate in the synthesis of Ubiquionone 10. Ubiquinone-4 is a Coenzyme Q analogue that have been identified in brain. Based on the isoprenoid moiety, the presence of various coenzyme Q homologues in prokaryotes and eurkaryotes has been confirmed, and these homologues are classified as Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, and Q12. The numbers, Qn, refer to the number of isoprenoid units attached at the 6- position on the benzoquinone ring of the coenzyme Q moiety. (PMID: 12064350 Link_out) Coenzyme Q is the only type of Quinone naturally found in animals (other quinones such as vitamin K is provided by foods). Coenzyme Q is a fat-soluble and amphipathic compound that is the integral component of the electron transport chain in mitochondria. It is ubiquitous in nature and is found in subcellular organelles, serum lipoproteins, blood plasma, urine, and feces. Ubiquinones are amphipathic because of the benzoquinone ring (hydrophilic) and the polyisoprenoid side chain moiety (lipophilic). The primary role of coenzyme Q is to transfer electrons between redox components of the electron transport chain, to create a proton gradient across the inner mitochondrial membrane and drive ATP formation. Additional functions of coenzyme Q are to influence membrane fluidity; to recycle the radical forms of vitamin C and E; and, most important, to act as a lipid antioxidant protecting membrane phospholipids against peroxidation. Coenzyme Q is the only endogenously occurring lipid-soluble antioxidant that occurs ubiquitously and can be synthesized in all organisms.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2,3-Dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-2,5-Cyclohexadiene-1,4-dione
  2. 2,3-Dimethoxy-5-methyl-6-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-p-Benzoquinone
  3. 2,3-Dimethoxy-5-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-2,5-Cyclohexadiene-1,4-dione
  4. Coenzyme Q4
  5. CoQ4
  6. Ubiquinone 4
  7. Ubiquinone Q4
Chemical Formula C29H42O4
Average Molecular Weight 454.6414
Monoisotopic Molecular Weight 454.308309832
IUPAC Name 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]cyclohexa-2,5-diene-1,4-dione
Traditional IUPAC Name coenzyme Q4
CAS Registry Number 4370-62-1
SMILES COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O
InChI Identifier InChI=1S/C29H42O4/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-17-23(5)18-19-25-24(6)26(30)28(32-7)29(33-8)27(25)31/h12,14,16,18H,9-11,13,15,17,19H2,1-8H3/b21-14+,22-16+,23-18+
InChI Key XGCJRRDNIMSYNC-INVBOZNNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Homomonocyclic Compounds
Class Benzoquinones
Sub Class N/A
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Ubiquinones(Lipidmaps)
Substituents
  • Isoprene
  • Ketone
Direct Parent Benzoquinones
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 6.53 ALOGPS
LogP 7.2 ChemAxon
LogS -5.71 ALOGPS
pKa (strongest basic) -4.7 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 52.6 A2 ChemAxon
Rotatable Bond Count 13 ChemAxon
Refractivity 143.79 ChemAxon
Polarizability 55.21 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB018340
KNApSAcK ID Not Available
Chemspider ID 4446658 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06710 Link_out
Metagene Link HMDB06710 Link_out
METLIN ID Not Available
PubChem Compound 5283545 Link_out
PDB ID Not Available
ChEBI ID 529178 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available