Livestock Metabolome Database: Showing metabocard for Monoethylhexyl phthalic acid (LMDB00583)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:53:04 UTC

Update Date

2016-07-20 21:02:10 UTC

Lmdb

LMDB00583

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(2-Ethylhexyl) hydrogen phthalate	ChEBI
1,2-Benzenedicarboxylic acid, mono(2-ethylhexyl) ester	ChEBI
2-([(2-Ethylhexyl)oxy]carbonyl)benzoic acid	ChEBI
2-Ethylhexyl hydrogen phthalate	ChEBI
2-Ethylhexyl phthalate	ChEBI
MEHP	ChEBI
mono(2-Ethylhexyl)phthalate	ChEBI
mono-(2-Ethylhexyl)phthalate	ChEBI
mono-2-Ethylhexyl phthalate	ChEBI
Monoethylhexyl phthalate	ChEBI
Phthalic acid, 2-ethylhexyl ester	ChEBI
(2-Ethylhexyl) hydrogen phthalic acid	Generator
1,2-Benzenedicarboxylate, mono(2-ethylhexyl) ester	Generator
2-([(2-Ethylhexyl)oxy]carbonyl)benzoate	Generator
2-Ethylhexyl hydrogen phthalic acid	Generator
2-Ethylhexyl phthalic acid	Generator
mono(2-Ethylhexyl)phthalic acid	Generator
mono-(2-Ethylhexyl)phthalic acid	Generator
mono-2-Ethylhexyl phthalic acid	Generator
Phthalate, 2-ethylhexyl ester	Generator
MEHP CPD	MeSH
mono(Ethylhexyl) phthalate	MeSH
mono-(2-Ethylhexyl)phthalate, sodium salt	MeSH
1,2-Benzenedicarboxylicacid,mono(2-ethylhexyl)ester	HMDB
mono-Ethylhexyl	HMDB
mono-Ethylhexylphthalate	HMDB
Monoethylhexyl phthalate (mehp)	HMDB
Monoethylhexylphthalate	HMDB
MONOOCTYL phthalATE	HMDB
Phthalic acid 1-hydrogen 2-(2-ethylhexyl) ester	HMDB
Phthalic acid hydrogen 1-(2-ethylhexyl) ester	HMDB
PHTHALIC ACID mono-2-ethylhexyl ester	HMDB
PHTHALIC ACID monooctyl ester	HMDB
Phthalicacid,2-ethylhexylester	HMDB
phthalicacidmono-2-ETHYLEXYLESTER	HMDB
PHTHALICACIDMONOETHYLHEXYL	HMDB
Phthalicacidmonoethylhexylester	HMDB
Monoethylhexyl phthalic acid	Generator
mono(2-Ethylhexyl) phthalic acid	Generator

Chemical Formula

C₁₆H₂₂O₄

Average Molecular Weight

278.3435

Monoisotopic Molecular Weight

278.151809192

IUPAC Name

2-{[(2-ethylhexyl)oxy]carbonyl}benzoic acid

Traditional Name

bar 1

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

Description

belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoic acid
Benzoyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dicarboxylic acid monoester (CHEBI:17243 )
phthalate ester (CHEBI:17243 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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
logP	4.36	ALOGPS
logP	4.66	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	77.49 m³·mol⁻¹	ChemAxon
Polarizability	30.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-2970000000-346112e2dd7eb2ef672f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00dj-2970000000-346112e2dd7eb2ef672f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-5920000000-6756fbba86aadca647ce	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-7392000000-fd40ccd8c52320562e5c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-006t-0960000000-efbb62fb904150b613f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-006t-0960000000-bace63e54682391af671	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00kb-0910000000-77eed661ab413010d354	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00mk-0900000000-214bdb75cf5614522a03	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00ai-0900000000-d636e4277afd375744d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001i-0900000000-e6f221aefc0e24f648d5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-002b-0900000000-d8cdf715271ec6e661b8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0059-0940000000-bbc0013de532edede483	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-004i-9100000000-d5a5ecd4f3c706f53a0f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00kb-0910000000-a2eba6e125597cb7530d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-00b9-2900000000-1d8439ed7614ed714822	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-004i-9800000000-3f611dc53f826ce06536	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fr-0790000000-972234c38f1e6baf9909	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-4930000000-1ab987bce4973d4f07f4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9500000000-53028683cce560c7a65b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0490000000-44a004dad8099c4e00de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00w9-1940000000-8169435369a241584a63	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00fr-6900000000-56a7cc157be52d6494f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0290000000-bf11acdb8d5f1fa06aa5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0532-2940000000-474dfefcab564610df5f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9500000000-0b315e8ad86892867d12	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0290000000-048ea11376b7fe328007	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-5950000000-012e94386a547e3c0c23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9410000000-a8dbecb62f34e602da89	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-4900000000-af0f2c76a7c01b845a00	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0013248

FooDB ID

FDB029358

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Monoethylhexyl phthalic acid (LMDB00583)

Structure for LMDB00583 (Monoethylhexyl phthalic acid)