General Information of MET (ID: META00793)
Name Azelaic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
1,7-Dicarboxyheptane; 1,7-Heptanedicarboxylate; 1,7-Heptanedicarboxylic acid; 1,9-Nonanedioate; 1,9-Nonanedioic acid; Acide azelaique; Acidum azelaicum; Anchoate; Anchoic acid; Azalaic acid; Azelaate; Azelaic acid, dilithium salt; Azelaic acid, dipotassium salt; Azelaic acid, disodium salt; Azelaic acid, monosodium salt; Azelaic acid, potassium salt; Azelaic acid, sodium salt; Azelaicacidtech; Azelainic acid; Azelainsaeure; Azelate; Azelex; Emerox 1110; Emerox 1144', Emery'S L-110, 'Finevin; Finacea; Heptanedicarboxylic acid; Lepargylate; Lepargylic acid; Monosodium azelate; N-Nonanedioate; N-Nonanedioic acid; Nonandisaeure; Nonanedioate; Nonanedioic acid; Nonanedioic acid azelaic acid; Nonanedioic acid homopolymer; Poly(azelaic anhydride); Polyazelaic anhydride; Skinorem; Skinoren
Source Endogenous;Escherichia Coli Metabolite;Fatty acyls;Food;Drug;Toxins/Pollutant;Cosmetic;TCM Ingredients;Microbial
Structure Type   Fatty acids and conjugates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Lipids and lipid-like molecules
Fatty Acyls
Fatty acids and conjugates
PubChem CID
2266
HMDB ID
HMDB0000784
Formula
C9H16O4
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C08261
DrugBank ID
DB00548
ChEBI ID
48131
FooDB ID
FDB012192
ChemSpider ID
2179
METLIN ID
5750
Physicochemical Properties Molecular Weight 188.22 Topological Polar Surface Area 74.6
XlogP 1.6 Complexity 147
Heavy Atom Count 13 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Function
Azelaic acid (AZA) is a naturally occurring saturated nine-carbon dicarboxylic acid (COOH (CH2)7-COOH). It possesses a variety of biological actions both in vitro and in vivo. Interest in the biological activity of AZA arose originally out of studies of skin surface lipids and the pathogenesis of hypochromia in pityriasis versicolor infection. Later, it was shown that Pityrosporum can oxidize unsaturated fatty acids to C8-C12 dicarboxylic acids that are cornpetitive inhibitors of tyrosinase in vitro. Azelaic acid was chosen for further investigation and development of a new topical drug for treating hyperpigmentary disorders for the following reasons: it possesses a middle-range of antityrosinase activity, is inexpensive, and more soluble to be incorporated into a base cream than other dicarboxylic acids. Azelaic acid is another option for the topical treatment of mild to moderate inflammatory acne vulgaris. It offers effectiveness similar to that of other agents without the systemic side effects of oral antibiotics or the allergic sensitization of topical benzoyl peroxide and with less irritation than tretinoin. Azelaic acid is less expensive than certain other prescription acne preparations, but it is much more expensive than nonprescription benzoyl peroxide preparations. Whether it is safe and effective when used in combination with other agents is not known.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of TP53
                      Induced Change Azelaic acid concentration: increase (Log2 FC=1.37)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of azelaic acid levels compared with control group.
References
1 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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