Details of Metabolite

General Information of MET (ID: META00643)
Name Monoethylhexyl phthalic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2-Ethylhexyl) hydrogen phthalate; (2-Ethylhexyl) hydrogen phthalic acid; 1,2-Benzenedicarboxylate, mono(2-ethylhexyl) ester; 1,2-Benzenedicarboxylic acid, mono(2-ethylhexyl) ester; 1,2-Benzenedicarboxylicacid,mono(2-ethylhexyl)ester; 2-([(2-Ethylhexyl)oxy]carbonyl)benzoate; 2-([(2-Ethylhexyl)oxy]carbonyl)benzoic acid; 2-Ethylhexyl hydrogen phthalate; 2-Ethylhexyl hydrogen phthalic acid; 2-Ethylhexyl phthalate; 2-Ethylhexyl phthalic acid; MEHP; MEHP CPD; MONOOCTYL phthalATE; Monoethylhexyl phthalate; Monoethylhexyl phthalate (mehp); Monoethylhexyl phthalic acid; Monoethylhexylphthalate; PHTHALIC ACID mono-2-ethylhexyl ester; PHTHALIC ACID monooctyl ester; PHTHALICACIDMONOETHYLHEXYL; Phthalate, 2-ethylhexyl ester; Phthalic acid 1-hydrogen 2-(2-ethylhexyl) ester; Phthalic acid hydrogen 1-(2-ethylhexyl) ester; Phthalic acid, 2-ethylhexyl ester; Phthalicacid,2-ethylhexylester; Phthalicacidmono-2-ethylexylester; Phthalicacidmonoethylhexylester; mono(2-Ethylhexyl) phthalic acid; mono(2-Ethylhexyl)phthalate; mono(2-Ethylhexyl)phthalic acid; mono(Ethylhexyl) phthalate; mono-(2-Ethylhexyl)phthalate; mono-(2-Ethylhexyl)phthalate, sodium salt; mono-(2-Ethylhexyl)phthalic acid; mono-2-Ethylhexyl phthalate; mono-2-Ethylhexyl phthalic acid; mono-Ethylhexyl; mono-Ethylhexylphthalate
Source Aromatic homomonocyclic compounds
Structure Type   Benzoic acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Benzenoids
Benzene and substituted derivatives
Benzoic acids and derivatives
PubChem CID
20393
HMDB ID
HMDB0013248
Formula
C16H22O4
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
C03343
ChEBI ID
17243
FooDB ID
FDB029358
ChemSpider ID
19208
Physicochemical Properties Molecular Weight 278.34 Topological Polar Surface Area 63.6
XlogP 4 Complexity 314
Heavy Atom Count 20 Rotatable Bond Count 9
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Function
Monoethylhexyl phthalic acid (MEHP) is an active metabolite of Bis(2-ethylhexyl)phthalate (DEHP). DEHP measured from the blood of pregnant women have been significantly associated with the decreased penis width, shorter anogenital distance, and the incomplete descent of testes of their newborn sons, replicating effects identified in animals. DEHP hydrolyzes to MEHP via the enzyme Bis(2-ethylhexyl)phthalate acylhydrolase(3.1.1.60)and subsequently to phthalate salts. The released alcohol is susceptible to oxidation to the aldehyde and carboxylic acid.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Amino acid/polyamine transporter (AAPT)
            Integral membrane E16 (SLC7A5) 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 Overexpression of SLC7A5
                      Induced Change Monoethylhexyl phthalic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC7A5 leads to the increase of monoethylhexyl phthalic acid levels compared with control group.
            L-type amino acid transporter 2 (LAT2) 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 Overexpression of SLC7A8
                      Induced Change Monoethylhexyl phthalic acid concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of SLC7A8 leads to the increase of monoethylhexyl phthalic acid levels compared with control group.
References
1 Transport of a neurotoxicant by molecular mimicry: the methylmercury-L-cysteine complex is a substrate for human L-type large neutral amino acid transporter (LAT) 1 and LAT2. Biochem J. 2002 Oct 1;367(Pt 1):239-46.

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