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Methylparaben (T3D3977)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (8)XML
Targets (8)
Record Information
Version2.0
Creation Date2014-08-29 04:48:27 UTC
Update Date2014-12-24 20:26:35 UTC
Accession NumberT3D3977
Identification
Common NameMethylparaben
ClassSmall Molecule
DescriptionMethylparaben is found in alcoholic beverages. Methylparaben is an antimicrobial agent, preservative, flavouring agent. Methylparaben is a constituent of cloudberry, yellow passion fruit, white wine, botrytised wine and Bourbon vanilla. Methylparaben has been shown to exhibit anti-microbial function Methylparaben belongs to the family of Hydroxybenzoic Acid Derivatives. These are compounds containing an hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxylic acid. (1).
Compound Type
  • Ester
  • Ether
  • Flavouring Agent
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Preservative
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
4-(Methoxycarbonyl)phenol
4-Hydroxybenzoic acid methyl ester
Benzoic acid, 4-hydroxy-, methyl ester
Benzoic acid, p-hydroxy-, methyl ester
Methyl 4-hydroxybenzoate
Methyl ester of p-hydroxybenzoic acid
Methyl p-hydroxybenzoate
Methyl p-oxybenzoate
Methyl paraben
Methyl parahydroxybenzoate
Methyl parasept
Methyl-p-hydroxybenzoate
Nipagin M
P-Carbomethoxyphenol
P-Hydroxybenzoic acid methyl ester
P-Hydroxybenzoic acid, methyl ester
P-Hydroxybenzoic methyl ester
P-Methoxycarbonylphenol
Tegosept M
Chemical FormulaC8H8O3
Average Molecular Mass152.147 g/mol
Monoisotopic Mass152.047 g/mol
CAS Registry Number99-76-3
IUPAC Namemethyl 4-hydroxybenzoate
Traditional Nameparaben
SMILESCOC(=O)C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
InChI KeyInChIKey=LXCFILQKKLGQFO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parentp-Hydroxybenzoic acid alkyl esters
Alternative Parents
Substituents
  • P-hydroxybenzoic acid alkyl ester
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point131°C
Boiling PointNot Available
Solubility2.5 mg/mL at 25°C
LogP1.96
Predicted Properties
PropertyValueSource
Water Solubility3.69 g/LALOGPS
logP2.17ALOGPS
logP1.67ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8.5ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.06 m³·mol⁻¹ChemAxon
Polarizability15.15 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-4900000000-5aa5692082b66b714b5dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-5900000000-f3eccc0d6c2c948bd57bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-4900000000-c5ef5603a5b5d1102f5aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-4900000000-5aa5692082b66b714b5dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-5900000000-f3eccc0d6c2c948bd57bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-4900000000-c5ef5603a5b5d1102f5aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5900000000-3ed4794b0abcfd130f36JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4920000000-b5bddbd000212b52d3e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e340d9e85783b175426eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0900000000-9f98d629ade444f4fbb1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9500000000-32f5caf98f5ad60ffa16JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-781a1ddebbdbcc9b39adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-41cbbcb3f2de007616e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-7900000000-f51bfe0dca5a352b0e11JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00di-7900000000-42b2fb742e91f0c75f63JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMethylparaben is found in alcoholic beverages.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB32572
PubChem Compound ID7456
ChEMBL IDCHEMBL325372
ChemSpider ID7176
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID31835
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDMPB
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3977.pdf
General References
  1. Gupta S, Kaisheva E: Development of a multidose formulation for a humanized monoclonal antibody using experimental design techniques. AAPS PharmSci. 2003;5(2):E8. [12866935 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Carbonic anhydrase 1
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular Weight:
28870.0 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory2.6 uMNot AvailableBindingDB 50209100
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
Target Details
2. Carbonic anhydrase 12
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA12
Uniprot ID:
O43570
Molecular Weight:
39450.615 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.82 uMNot AvailableBindingDB 50209100
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
Target Details
3. Carbonic anhydrase 14
General Function:
Metal ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA14
Uniprot ID:
Q9ULX7
Molecular Weight:
37667.37 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory4.1 uMNot AvailableBindingDB 50209100
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
Target Details
4. Carbonic anhydrase 2
General Function:
Zinc ion binding
Specific Function:
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye. Contributes to intracellular pH regulation in the duodenal upper villous epithelium during proton-coupled peptide absorption. Stimulates the chloride-bicarbonate exchange activity of SLC26A6.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular Weight:
29245.895 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory3.4 uMNot AvailableBindingDB 50209100
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
Target Details
5. Carbonic anhydrase 7
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide.
Gene Name:
CA7
Uniprot ID:
P43166
Molecular Weight:
29658.235 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.78 uMNot AvailableBindingDB 50209100
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
Target Details
6. Carbonic anhydrase 9
General Function:
Zinc ion binding
Specific Function:
Reversible hydration of carbon dioxide. Participates in pH regulation. May be involved in the control of cell proliferation and transformation. Appears to be a novel specific biomarker for a cervical neoplasia.
Gene Name:
CA9
Uniprot ID:
Q16790
Molecular Weight:
49697.36 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory5.5 uMNot AvailableBindingDB 50209100
References
  1. Carta F, Vullo D, Maresca A, Scozzafava A, Supuran CT: Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15;21(6):1564-9. doi: 10.1016/j.bmc.2012.05.019. Epub 2012 May 17. [22668600 ]
Target Details
7. Peroxisome proliferator-activated receptor gamma
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da
References
  1. Pereira-Fernandes A, Demaegdt H, Vandermeiren K, Hectors TL, Jorens PG, Blust R, Vanparys C: Evaluation of a screening system for obesogenic compounds: screening of endocrine disrupting compounds and evaluation of the PPAR dependency of the effect. PLoS One. 2013 Oct 14;8(10):e77481. doi: 10.1371/journal.pone.0077481. eCollection 2013. [24155963 ]
Target Details
8. Xanthine dehydrogenase/oxidase
General Function:
Xanthine oxidase activity
Specific Function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular Weight:
146422.99 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50>50 uMNot AvailableBindingDB 50209100
References
  1. Cioffi G, D'Auria M, Braca A, Mendez J, Castillo A, Morelli I, De Simone F, De Tommasi N: Antioxidant and free-radical scavenging activity of constituents of the leaves of Tachigalia paniculata. J Nat Prod. 2002 Nov;65(11):1526-9. [12444671 ]