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Human Metabolome Database Version 3.5

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Showing metabocard for Malondialdehyde (HMDB06112)

Record Information
Version 3.5
Creation Date 2007-04-12 17:22:02 -0600
Update Date 2013-02-08 17:14:32 -0700
HMDB ID HMDB06112
Secondary Accession Numbers None
Metabolite Identification
Common Name Malondialdehyde
Description Malondialdehyde (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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,3-Propanedial
  2. 1,3-Propanedialdehyde
  3. 1,3-Propanedione
  4. Malonaldehyde
  5. Malonic aldehyde
  6. Malonic dialdehyde
  7. Malonodialdehyde
  8. Malonyldialdehyde
  9. MDD
  10. Propanedial
Chemical Formula C3H4O2
Average Molecular Weight 72.0627
Monoisotopic Molecular Weight 72.021129372
IUPAC Name propanedial
Traditional IUPAC Name malonaldehyde
CAS Registry Number 542-78-9
SMILES O=CCC=O
InChI Identifier InChI=1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2
InChI Key WSMYVTOQOOLQHP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Carbonyl Compounds
Sub Class Aldehydes
Other Descriptors
  • Aliphatic Acyclic Compounds
  • dialdehyde(ChEBI)
Substituents
  • N/A
Direct Parent Aldehydes
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 72 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 241 g/L ALOGPS
LogP 0.10 ALOGPS
LogP -0.65 ChemAxon
LogS 0.52 ALOGPS
pKa (strongest acidic) 6.68 ChemAxon
pKa (strongest basic) -6.8 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 34.14 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 17.14 ChemAxon
Polarizability 6.42 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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0.69 +/- 0.13 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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2.36 +/- 0.55 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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3.85 (1.7 - 8.3) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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0.22 +/- 0.089 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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0.002 +/- 0.0002 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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0.0013 +/- 0.0002 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.32 +/- 0.073 uM Not Specified Not Specified Guillain-Barre syndrome (GBS) Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.22 +/- 0.06 uM Not Specified Not Specified multiple sclerosis Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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5.3 (0.38 - 55.0) uM Adult (>18 years old) Both Parkinson's disease Not Available
Associated Disorders and Diseases
Disease References
Parkinson's disease
  • 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. Pubmed: 17145675 Link_out
    Smoking
    • 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. Pubmed: 18029489 Link_out
      Associated OMIM IDs
      DrugBank ID DB03057 Link_out
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB008116
      KNApSAcK ID Not Available
      Chemspider ID 10499 Link_out
      KEGG Compound ID C19440 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Malondialdehyde Link_out
      NuGOwiki Link HMDB06112 Link_out
      Metagene Link HMDB06112 Link_out
      METLIN ID Not Available
      PubChem Compound 10964 Link_out
      PDB ID MDD Link_out
      ChEBI ID 566274 Link_out
      References
      Synthesis Reference Not Available
      Material Safety Data Sheet (MSDS) Not Available
      General References Not Available