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Human Metabolome Database Version 3.5

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Showing metabocard for Monoethylhexyl phthalic acid (HMDB13248)

Record Information
Version 3.5
Creation Date 2009-11-30 08:51:40 -0700
Update Date 2013-02-08 17:29:59 -0700
HMDB ID HMDB13248
Secondary Accession Numbers None
Metabolite Identification
Common Name Monoethylhexyl phthalic acid
Description 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(Wikipedia). 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,2-Benzenedicarboxylicacid,mono(2-ethylhexyl)ester
  2. 2-ETHYLHEXYL HYDROGEN PHTHALATE
  3. MEHP
  4. MONO-2-ETHYLHEXYL PHTHALATE
  5. Mono-ethylhexyl
  6. Mono-ethylhexylphthalate
  7. Monoethylhexyl phthalate (mEHP)
  8. Monoethylhexylphthalate
  9. MONOOCTYL PHTHALATE
  10. Phthalic acid 1-hydrogen 2-(2-ethylhexyl) ester
  11. Phthalic acid hydrogen 1-(2-ethylhexyl) ester
  12. PHTHALIC ACID MONO-2-ETHYLHEXYL ESTER
  13. PHTHALIC ACID MONOOCTYL ESTER
  14. Phthalicacid,2-ethylhexylester
  15. PHTHALICACIDMONO-2-ETHYLEXYLESTER
  16. PHTHALICACIDMONOETHYLHEXYL
  17. Phthalicacidmonoethylhexylester
Chemical Formula C16H22O4
Average Molecular Weight 278.3435
Monoisotopic Molecular Weight 278.151809192
IUPAC Name 2-{[(2-ethylhexyl)oxy]carbonyl}benzoic acid
Traditional IUPAC Name monoethylhexyl phthalate
CAS Registry Number 4376-20-9
SMILES CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O
InChI Identifier InChI=1S/C16H22O4/c1-3-5-8-12(4-2)11-20-16(19)14-10-7-6-9-13(14)15(17)18/h6-7,9-10,12H,3-5,8,11H2,1-2H3,(H,17,18)
InChI Key DJDSLBVSSOQSLW-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzoic Acid and Derivatives
Sub Class Phthalic Acid and Derivatives
Other Descriptors
  • Organic Compounds
  • dicarboxylic acid monoester(ChEBI)
  • phthalate ester(ChEBI)
Substituents
  • Benzoyl
  • Carboxylic Acid
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
Direct Parent o-Phthalic Acid and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available 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 0.013 g/L ALOGPS
LogP 4.36 ALOGPS
LogP 4.66 ChemAxon
LogS -4.32 ALOGPS
pKa (strongest acidic) 3.08 ChemAxon
pKa (strongest basic) -7 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 63.6 A2 ChemAxon
Rotatable Bond Count 9 ChemAxon
Refractivity 77.49 ChemAxon
Polarizability 30.96 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029358
KNApSAcK ID Not Available
Chemspider ID 19208 Link_out
KEGG Compound ID C03343 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB13248 Link_out
Metagene Link HMDB13248 Link_out
METLIN ID Not Available
PubChem Compound 20393 Link_out
PDB ID Not Available
ChEBI ID 17243 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available