Methyl p-hydroxybenzoate
Relevant Data
Food Additives Approved in the United States
Food Additives Approved by WHO:
General Information
| Chemical name | Methyl p-hydroxybenzoate |
| E No. | E 218 |
| INS. | 218 |
| CAS number | 99-76-3 |
| Group | No |
| Component of the group |
Sorbic acid - sorbates; p-hydroxybenzoates (E 200 - 203; 214 - 219) Sorbic acid - sorbates; Benzoic acid - benzoates; p-hydroxybenzoates (E 200 - 219) p-hydroxybenzoates (PHB) (E 214 - 219) |
From webgate.ec.europa.eu
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 7456 |
| IUPAC Name | methyl 4-hydroxybenzoate |
| InChI | InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 |
| InChI Key | LXCFILQKKLGQFO-UHFFFAOYSA-N |
| Canonical SMILES | COC(=O)C1=CC=C(C=C1)O |
| Molecular Formula | C8H8O3 |
| Wikipedia | methylparaben |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 152.149 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Complexity | 136.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B w M A A A A A A A A A A A A A A A A A A A A A A A A A A w A A A A A A A A A A A B A A A A G g A A C A A A D A S A m A I y D o A A B g C I A i D S C A A C A A A k I A A I i A E G C M g I J j K C N R q A c Q A k w B E I u Y e I 7 C z O I A A A A A A A A A B A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 46.5 |
| Monoisotopic Mass | 152.047 |
| Exact Mass | 152.047 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.7427 |
| Human Intestinal Absorption | HIA+ | 0.9887 |
| Caco-2 Permeability | Caco2+ | 0.8682 |
| P-glycoprotein Substrate | Non-substrate | 0.7105 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9617 |
| Non-inhibitor | 0.9644 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8791 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.9255 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7458 |
| CYP450 2D6 Substrate | Non-substrate | 0.9172 |
| CYP450 3A4 Substrate | Non-substrate | 0.6947 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6776 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9764 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9848 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9503 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9761 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9640 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9493 |
| Non-inhibitor | 0.9791 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.8321 |
| Fish Toxicity | High FHMT | 0.7015 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8900 |
| Honey Bee Toxicity | High HBT | 0.8502 |
| Biodegradation | Ready biodegradable | 0.8781 |
| Acute Oral Toxicity | III | 0.8243 |
| Carcinogenicity (Three-class) | Non-required | 0.5851 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.8579 | LogS |
| Caco-2 Permeability | 1.1158 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8917 | LD50, mol/kg |
| Fish Toxicity | 1.9309 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.0748 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | None |
|---|---|
| Mechanism of Toxicity | None |
| Metabolism | None |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | None |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Benzoic acid esters - p-Hydroxybenzoic acid esters |
| Direct Parent | p-Hydroxybenzoic acid alkyl esters |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| 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 |
| Description | This compound 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. |
From ClassyFire
Targets
- 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
References
- 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 ]
- 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
References
- 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 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA12
- Uniprot ID:
- O43570
- Molecular Weight:
- 39450.615 Da
References
- 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 ]
- General Function:
- Metal ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA14
- Uniprot ID:
- Q9ULX7
- Molecular Weight:
- 37667.37 Da
References
- 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 ]
- 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
References
- 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 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Reversible hydration of carbon dioxide.
- Gene Name:
- CA7
- Uniprot ID:
- P43166
- Molecular Weight:
- 29658.235 Da
References
- 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 ]
- 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
References
- 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 ]
- 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
- 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 ]
From T3DB