PROPYL GALLATE
Relevant Data
Food Additives Approved by WHO:
Food Additives Approved by European Union:
General Information
| Mainterm | PROPYL GALLATE |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 121-79-9 |
| Regnum |
175.300 176.170 177.1010 175.380 175.390 177.1210 166.110 175.125 177.1350 181.24 172.615 184.1660 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 4947 |
| IUPAC Name | propyl 3,4,5-trihydroxybenzoate |
| InChI | InChI=1S/C10H12O5/c1-2-3-15-10(14)6-4-7(11)9(13)8(12)5-6/h4-5,11-13H,2-3H2,1H3 |
| InChI Key | ZTHYODDOHIVTJV-UHFFFAOYSA-N |
| Canonical SMILES | CCCOC(=O)C1=CC(=C(C(=C1)O)O)O |
| Molecular Formula | C10H12O5 |
| Wikipedia | propyl gallate |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 212.201 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Complexity | 206.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B w O 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 g 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 A i A E G i M g J J z K C N R q C c Q E l w B U J u Y f K 7 D z O I A A B C A A A Q A B A A A I Q A A C A A A A A A A A A A A = = |
| Topological Polar Surface Area | 87.0 |
| Monoisotopic Mass | 212.068 |
| Exact Mass | 212.068 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| 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- | 0.7732 |
| Human Intestinal Absorption | HIA+ | 0.8757 |
| Caco-2 Permeability | Caco2- | 0.5111 |
| P-glycoprotein Substrate | Substrate | 0.5456 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8856 |
| Non-inhibitor | 0.9488 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9064 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8899 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8079 |
| CYP450 2D6 Substrate | Non-substrate | 0.8665 |
| CYP450 3A4 Substrate | Non-substrate | 0.5778 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.6708 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6852 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9062 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6469 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9238 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8852 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9513 |
| Non-inhibitor | 0.8556 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9176 |
| Fish Toxicity | High FHMT | 0.8489 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9978 |
| Honey Bee Toxicity | High HBT | 0.6198 |
| Biodegradation | Ready biodegradable | 0.9475 |
| Acute Oral Toxicity | III | 0.8982 |
| Carcinogenicity (Three-class) | Non-required | 0.7321 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.7640 | LogS |
| Caco-2 Permeability | 0.1312 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9742 | LD50, mol/kg |
| Fish Toxicity | 1.0676 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7665 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | |
|---|---|
| Mechanism of Toxicity | |
| Metabolism | |
| Toxicity Values | |
| Lethal Dose | |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | |
| Health Effects | |
| Treatment | |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Hydroxybenzoic acid derivatives - Gallic acid and derivatives |
| Direct Parent | Galloyl esters |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Galloyl ester - P-hydroxybenzoic acid alkyl ester - M-hydroxybenzoic acid ester - P-hydroxybenzoic acid ester - Benzoate ester - Benzenetriol - Pyrogallol derivative - Benzoyl - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Polyol - Organooxygen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid. |
From ClassyFire
Targets
- General Function:
- Ubiquitin-protein transferase activity
- Specific Function:
- Transcription factor with important functions in the development of the eye, nose, central nervous system and pancreas. Required for the differentiation of pancreatic islet alpha cells (By similarity). Competes with PAX4 in binding to a common element in the glucagon, insulin and somatostatin promoters. Regulates specification of the ventral neuron subtypes by establishing the correct progenitor domains (By similarity). Isoform 5a appears to function as a molecular switch that specifies target genes.
- Gene Name:
- PAX6
- Uniprot ID:
- P26367
- Molecular Weight:
- 46683.075 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Ligand-activated transcription factor. Receptor for bile acids such as chenodeoxycholic acid, lithocholic acid and deoxycholic acid. Represses the transcription of the cholesterol 7-alpha-hydroxylase gene (CYP7A1) through the induction of NR0B2 or FGF19 expression, via two distinct mechanisms. Activates the intestinal bile acid-binding protein (IBABP). Activates the transcription of bile salt export pump ABCB11 by directly recruiting histone methyltransferase CARM1 to this locus.
- Gene Name:
- NR1H4
- Uniprot ID:
- Q96RI1
- Molecular Weight:
- 55913.915 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Transcriptional activator activity, rna polymerase ii distal enhancer sequence-specific binding
- Specific Function:
- Transcription activator that binds to antioxidant response (ARE) elements in the promoter regions of target genes. Important for the coordinated up-regulation of genes in response to oxidative stress. May be involved in the transcriptional activation of genes of the beta-globin cluster by mediating enhancer activity of hypersensitive site 2 of the beta-globin locus control region.
- Gene Name:
- NFE2L2
- Uniprot ID:
- Q16236
- Molecular Weight:
- 67825.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- Amadasi A, Mozzarelli A, Meda C, Maggi A, Cozzini P: Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach. Chem Res Toxicol. 2009 Jan;22(1):52-63. doi: 10.1021/tx800048m. [19063592 ]
From T3DB