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Record Information
Version3.6
Creation Date2007-04-12 23:22:02 UTC
Update Date2016-10-18 21:31:04 UTC
HMDB IDHMDB06112
Secondary Accession NumbersNone
Metabolite Identification
Common NameMalondialdehyde
DescriptionMalondialdehyde (MDA) is the dialdehyde of malonic acid and a biomarker of oxidative damage to lipids caused by smoking. Oxidized lipids are able to produce MDA as a decomposition product. The mechanism is thought to involve formation of prostaglandin-like endoperoxides from polyunsaturated fatty acids with two or more double bonds. An alternative mechanism is based on successive hydroperoxide formation and β-cleavage of polyunsaturated fatty acids. MDA is then directly formed by β-scission of a 3-hydroperoxyaldehyde or by reaction between acrolein and hydroxyl radicals. While oxidation of polyunsaturated fatty acids is the major source of MDA in vivo, other minor sources exists such as byproducts of free radical generation by ionizing radiation and of the biosynthesis of prostaglandins. Aldehydes are generally reactive species capable of forming adducts and complexes in biological systems and MDA is no exception although the main species at physiological pH is the enolate ion which is of relative low reactivity. Consistent evidence is available for the reaction between MDA and cellular macromolecules such as proteins, RNA and DNA. MDA reacts with DNA to form adducts to deoxyguanosine and deoxyadenosine which may be mutagenic and these can be quantified in several human tissues. Oxidative stress is an imbalance between oxidants and antioxidants on a cellular or individual level. Oxidative damage is one result of such an imbalance and includes oxidative modification of cellular macromolecules, induction of cell death by apoptosis or necrosis, as well as structural tissue damage. Chemically speaking, oxidants are compounds capable of oxidizing target molecules. This can take place in three ways: abstraction of hydrogen, abstraction of electrons or addition of oxygen. All cells living under aerobic conditions are continuously exposed to a large numbers of oxidants derived from various endogenous and exogenous sources. The endogenous sources of oxidants are several and include the respiratory chain in the mitochondria, immune reactions, enzymes such as xanthine oxidase and nitric oxide synthase and transition metal mediated oxidation. Various exogenous sources of ROS also contribute directly or indirectly to the total oxidant load. These include effects of ionizing and non-ionizing radiation, air pollution and natural toxic gases such as ozone, and chemicals and toxins including oxidizing disinfectants. A poor diet containing inadequate amounts of nutrients may also indirectly result in oxidative stress by impairing cellular defense mechanisms. The cellular macromolecules, in particular lipids, proteins and DNA, are natural targets of oxidation. Oxidants are capable of initiating lipid oxidation by abstraction of an allylic proton from a polyunsaturated fatty acid. This process, by multiple stages leading to the formation of lipid hydroperoxides, is a known contributor to the development of atherosclerosis. (PMID: 17336279 ).
Structure
Thumb
Synonyms
ValueSource
1,3-PropanedialHMDB
1,3-PropanedialdehydeHMDB
1,3-PropanedioneHMDB
MalonaldehydeHMDB
Malonic aldehydeHMDB
Malonic dialdehydeHMDB
MalonodialdehydeHMDB
MalonyldialdehydeHMDB
MDDHMDB
PropanedialHMDB
Chemical FormulaC3H4O2
Average Molecular Weight72.0627
Monoisotopic Molecular Weight72.021129372
IUPAC Namepropanedial
Traditional Namemalonaldehyde
CAS Registry Number542-78-9
SMILES
O=CCC=O
InChI Identifier
InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2
InChI KeyInChIKey=WSMYVTOQOOLQHP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub Class1,3-dicarbonyl compounds
Direct Parent1,3-dicarbonyl compounds
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
  • Alpha-hydrogen aldehyde
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point72 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility241.0 mg/mLALOGPS
logP0.1ALOGPS
logP-0.65ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)6.68ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity17.14 m3·mol-1ChemAxon
Polarizability6.42 Å3ChemAxon
Number of Rings0ChemAxon
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, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.71 +/- 0.50 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.69 +/- 0.13 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.58 +/- 1.13 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified2.36 +/- 0.55 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified3.85 (1.7 - 8.3) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.22 +/- 0.089 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0013 +/- 0.0002 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.76 +/- 0.79 uMAdult (>18 years old)BothSchizophrenia details
BloodDetected and Quantified5.40 +/- 0.30 uMAdult (>18 years old)Bothuremia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.32 +/- 0.073 uMNot SpecifiedNot SpecifiedGuillain-Barre syndrome (GBS) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.22 +/- 0.06 uMNot SpecifiedNot Specifiedmultiple sclerosis details
Cerebrospinal Fluid (CSF)Detected and Quantified5.3 (0.38 - 55.0) uMAdult (>18 years old)BothParkinson's disease details
UrineDetected and Quantified0.002 +/- 0.0002 umol/mmol creatinineAdult (>18 years old)BothSmoking details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Kuloglu M, Ustundag B, Atmaca M, Canatan H, Tezcan AE, Cinkilinc N: Lipid peroxidation and antioxidant enzyme levels in patients with schizophrenia and bipolar disorder. Cell Biochem Funct. 2002 Jun;20(2):171-5. [11979513 ]
Parkinson's disease
  1. Shukla R, Rajani M, Srivastava N, Barthwal MK, Dikshit M: Nitrite and malondialdehyde content in cerebrospinal fluid of patients with Parkinson's disease. Int J Neurosci. 2006 Dec;116(12):1391-402. [17145675 ]
Smoking
  1. Li N, Jia X, Chen CY, Blumberg JB, Song Y, Zhang W, Zhang X, Ma G, Chen J: Almond consumption reduces oxidative DNA damage and lipid peroxidation in male smokers. J Nutr. 2007 Dec;137(12):2717-22. [18029489 ]
Associated OMIM IDs
DrugBank IDDB03057
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008116
KNApSAcK IDNot Available
Chemspider ID10499
KEGG Compound IDC19440
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMalondialdehyde
NuGOwiki LinkHMDB06112
Metagene LinkHMDB06112
METLIN IDNot Available
PubChem Compound10964
PDB IDMDD
ChEBI ID566274
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lykkesfeldt J: Malondialdehyde as biomarker of oxidative damage to lipids caused by smoking. Clin Chim Acta. 2007 May 1;380(1-2):50-8. Epub 2007 Feb 7. [17336279 ]