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Record Information
Version3.6
Creation Date2012-10-30 10:32:48 UTC
Update Date2016-02-11 07:50:30 UTC
HMDB IDHMDB59661
Secondary Accession NumbersNone
Metabolite Identification
Common NameQH(2)
DescriptionQh(2) is part of the Oxidative phosphorylation, Cardiac muscle contraction, Alzheimer's disease, Parkinson's disease, and Huntington's disease pathways. It is a substrate for: Cytochrome b-c1 complex subunit Rieske, mitochondrial.
Structure
Thumb
Synonyms
ValueSource
Ubiquinol(1)MetaCyc
Chemical FormulaC14H20O4
Average Molecular Weight252.3062
Monoisotopic Molecular Weight252.136159128
IUPAC Name2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol
Traditional Name2,3-dimethoxy-5-methyl-6-(3-methylbut-2-en-1-yl)benzene-1,4-diol
CAS Registry NumberNot Available
SMILES
COC1=C(O)C(C)=C(CC=C(C)C)C(O)=C1OC
InChI Identifier
InChI=1S/C14H20O4/c1-8(2)6-7-10-9(3)11(15)13(17-4)14(18-5)12(10)16/h6,15-16H,7H2,1-5H3
InChI KeyInChIKey=TVLSKGDBUQMDPR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as prenylated hydroquinones. These are quinones with a structure characterized by the hydroquinone ring substituted by an prenyl side-chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentPrenylated hydroquinones
Alternative Parents
Substituents
  • Prenylbenzoquinol
  • Ubiquinol skeleton
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Hydroxyquinol derivative
  • Methoxybenzene
  • Phenol ether
  • O-cresol
  • M-cresol
  • Hydroquinone
  • Anisole
  • Toluene
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.31 mg/mLALOGPS
logP2.7ALOGPS
logP3.29ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)10.27ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.23 m3·mol-1ChemAxon
Polarizability27.93 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0190000000-a6ad04484f30fd3e6542View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-3890000000-88f5855287f7c4803858View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-6910000000-2566d9b9220bdfd47f6eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d3c87a4ee5f1fc3e1e44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-1790000000-f43f7dda07b2e0c3a516View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00y0-8920000000-223ce579fce165e10c55View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
2-ketoglutarate dehydrogenase complex deficiencySMP00549Not Available
Citric Acid CycleSMP00057map00020
Congenital lactic acidosisSMP00546Not Available
Fumarase deficiencySMP00547Not Available
Mitochondrial complex II deficiencySMP00548Not Available
Pyruvate dehydrogenase deficiency (E2)SMP00551Not Available
Pyruvate dehydrogenase deficiency (E3)SMP00550Not Available
The oncogenic action of 2-hydroxyglutarateSMP02291Not Available
The oncogenic action of D-2-hydroxyglutarate in Hydroxygluaricaciduria SMP02359Not Available
The oncogenic action of L-2-hydroxyglutarate in HydroxygluaricaciduriaSMP02358Not Available
Warburg EffectSMP00654Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID394877
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB59661
Metagene LinkHMDB59661
METLIN IDNot Available
PubChem Compound447920
PDB IDNot Available
ChEBI ID17976
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidation reduction
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND1
Uniprot ID:
P03886
Molecular weight:
35660.055
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
NDUFS2
Uniprot ID:
O75306
Molecular weight:
51851.59
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND4L
Uniprot ID:
P03901
Molecular weight:
10741.005
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND5
Uniprot ID:
P03915
Molecular weight:
67025.67
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in oxidoreductase activity, acting on NADH or NADPH
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
NDUFS3
Uniprot ID:
O75489
Molecular weight:
30241.245
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in oxidoreductase activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
NDUFV2
Uniprot ID:
P19404
Molecular weight:
27391.36
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in electron carrier activity
Specific function:
Flavoprotein (FP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q). Can act as a tumor suppressor.
Gene Name:
SDHA
Uniprot ID:
P31040
Molecular weight:
72690.975
Reactions
Succinic acid + Coenzyme Q10 → Fumaric acid + QH(2)details
General function:
Involved in electron carrier activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity). May donate electrons to ubiquinone.
Gene Name:
NDUFS8
Uniprot ID:
O00217
Molecular weight:
23704.795
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND2
Uniprot ID:
P03891
Molecular weight:
38960.47
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in electron carrier activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity). This is the largest subunit of complex I and it is a component of the iron-sulfur (IP) fragment of the enzyme. It may form part of the active site crevice where NADH is oxidized.
Gene Name:
NDUFS1
Uniprot ID:
P28331
Molecular weight:
67523.595
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in electron-transferring-flavoprotein dehydrogenase activity
Specific function:
Accepts electrons from ETF and reduces ubiquinone.
Gene Name:
ETFDH
Uniprot ID:
Q16134
Molecular weight:
68494.96
Reactions
Reduced electron-transferring flavoprotein + Coenzyme Q10 → electron-transferring flavoprotein + QH(2)details
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND4
Uniprot ID:
P03905
Molecular weight:
51580.26
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
NDUFS7
Uniprot ID:
O75251
Molecular weight:
23563.3
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND3
Uniprot ID:
P03897
Molecular weight:
13185.87
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
NDUFV1
Uniprot ID:
P49821
Molecular weight:
49867.66
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in NADH dehydrogenase (ubiquinone) activity
Specific function:
Core subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I) that is believed to belong to the minimal assembly required for catalysis. Complex I functions in the transfer of electrons from NADH to the respiratory chain. The immediate electron acceptor for the enzyme is believed to be ubiquinone (By similarity).
Gene Name:
MT-ND6
Uniprot ID:
P03923
Molecular weight:
18622.045
Reactions
NADH + Coenzyme Q10 → NAD + QH(2)details
General function:
Involved in electron carrier activity
Specific function:
Iron-sulfur protein (IP) subunit of succinate dehydrogenase (SDH) that is involved in complex II of the mitochondrial electron transport chain and is responsible for transferring electrons from succinate to ubiquinone (coenzyme Q).
Gene Name:
SDHB
Uniprot ID:
P21912
Molecular weight:
31629.365
Reactions
Succinic acid + Coenzyme Q10 → Fumaric acid + QH(2)details