PHENYLACETIC ACID
Relevant Data
Food Additives Approved by WHO:
Flavouring Substances Approved by European Union:
General Information
| Mainterm | PHENYLACETIC ACID |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 103-82-2 |
| Regnum |
172.515 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 999 |
| IUPAC Name | 2-phenylacetic acid |
| InChI | InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10) |
| InChI Key | WLJVXDMOQOGPHL-UHFFFAOYSA-N |
| Canonical SMILES | C1=CC=C(C=C1)CC(=O)O |
| Molecular Formula | C8H8O2 |
| Wikipedia | phenylacetate |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 136.15 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Complexity | 114.0 |
| 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 C A m A A w C I A A A g C I A i D S C A A C A A A g A A A I i A E A A I g I I D K A F R C A Y A A k w A E I i A e I y K C 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 A A A A = = |
| Topological Polar Surface Area | 37.3 |
| Monoisotopic Mass | 136.052 |
| Exact Mass | 136.052 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| 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
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9469 |
| Human Intestinal Absorption | HIA+ | 0.9808 |
| Caco-2 Permeability | Caco2+ | 0.8809 |
| P-glycoprotein Substrate | Non-substrate | 0.8151 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9791 |
| Non-inhibitor | 0.9919 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9240 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6387 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8016 |
| CYP450 2D6 Substrate | Non-substrate | 0.9451 |
| CYP450 3A4 Substrate | Non-substrate | 0.8274 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8697 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9899 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9481 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9861 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9777 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9810 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9519 |
| Non-inhibitor | 0.9812 | |
| AMES Toxicity | Non AMES toxic | 0.9754 |
| Carcinogens | Non-carcinogens | 0.6428 |
| Fish Toxicity | High FHMT | 0.7456 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9444 |
| Honey Bee Toxicity | High HBT | 0.6850 |
| Biodegradation | Ready biodegradable | 0.8608 |
| Acute Oral Toxicity | III | 0.8575 |
| Carcinogenicity (Three-class) | Non-required | 0.7745 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.0061 | LogS |
| Caco-2 Permeability | 1.6254 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8134 | LD50, mol/kg |
| Fish Toxicity | 2.0672 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3590 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Endogenous, Ingestion, Dermal (contact) |
|---|---|
| Mechanism of Toxicity | Uremic toxins such as phenylacetic acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) . Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species |
| Metabolism | Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces. |
| 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 | Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
| Treatment | Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzene and substituted derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Monocyclic benzene moiety - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. |
From ClassyFire
Targets
- General Function:
- Sh2 domain binding
- Specific Function:
- Non-receptor tyrosine-protein kinase that plays an essential role in the selection and maturation of developing T-cells in the thymus and in the function of mature T-cells. Plays a key role in T-cell antigen receptor (TCR)-linked signal transduction pathways. Constitutively associated with the cytoplasmic portions of the CD4 and CD8 surface receptors. Association of the TCR with a peptide antigen-bound MHC complex facilitates the interaction of CD4 and CD8 with MHC class II and class I molecules, respectively, thereby recruiting the associated LCK protein to the vicinity of the TCR/CD3 complex. LCK then phosphorylates tyrosines residues within the immunoreceptor tyrosine-based activation motifs (ITAM) of the cytoplasmic tails of the TCR-gamma chains and CD3 subunits, initiating the TCR/CD3 signaling pathway. Once stimulated, the TCR recruits the tyrosine kinase ZAP70, that becomes phosphorylated and activated by LCK. Following this, a large number of signaling molecules are recruited, ultimately leading to lymphokine production. LCK also contributes to signaling by other receptor molecules. Associates directly with the cytoplasmic tail of CD2, which leads to hyperphosphorylation and activation of LCK. Also plays a role in the IL2 receptor-linked signaling pathway that controls the T-cell proliferative response. Binding of IL2 to its receptor results in increased activity of LCK. Is expressed at all stages of thymocyte development and is required for the regulation of maturation events that are governed by both pre-TCR and mature alpha beta TCR. Phosphorylates other substrates including RUNX3, PTK2B/PYK2, the microtubule-associated protein MAPT, RHOH or TYROBP.
- Gene Name:
- LCK
- Uniprot ID:
- P06239
- Molecular Weight:
- 58000.15 Da
References
- Hajduk PJ, Zhou MM, Fesik SW: NMR-based discovery of phosphotyrosine mimetics that bind to the Lck SH2 domain. Bioorg Med Chem Lett. 1999 Aug 16;9(16):2403-6. [10476877 ]
- General Function:
- Glyceraldehyde oxidoreductase activity
- Specific Function:
- Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
- Gene Name:
- AKR1B1
- Uniprot ID:
- P15121
- Molecular Weight:
- 35853.125 Da
References
- Ferrari AM, Degliesposti G, Sgobba M, Rastelli G: Validation of an automated procedure for the prediction of relative free energies of binding on a set of aldose reductase inhibitors. Bioorg Med Chem. 2007 Dec 15;15(24):7865-77. Epub 2007 Aug 22. [17870536 ]
- General Function:
- Vitamin d binding
- Specific Function:
- May have weak glycosidase activity towards glucuronylated steroids. However, it lacks essential active site Glu residues at positions 239 and 872, suggesting it may be inactive as a glycosidase in vivo. May be involved in the regulation of calcium and phosphorus homeostasis by inhibiting the synthesis of active vitamin D (By similarity). Essential factor for the specific interaction between FGF23 and FGFR1 (By similarity).The Klotho peptide generated by cleavage of the membrane-bound isoform may be an anti-aging circulating hormone which would extend life span by inhibiting insulin/IGF1 signaling.
- Gene Name:
- KL
- Uniprot ID:
- Q9UEF7
- Molecular Weight:
- 116179.815 Da
References
- Young GH, Wu VC: KLOTHO methylation is linked to uremic toxins and chronic kidney disease. Kidney Int. 2012 Apr;81(7):611-2. doi: 10.1038/ki.2011.461. [22419041 ]
- General Function:
- Superoxide-generating nadph oxidase activity
- Specific Function:
- Constitutive NADPH oxidase which generates superoxide intracellularly upon formation of a complex with CYBA/p22phox. Regulates signaling cascades probably through phosphatases inhibition. May function as an oxygen sensor regulating the KCNK3/TASK-1 potassium channel and HIF1A activity. May regulate insulin signaling cascade. May play a role in apoptosis, bone resorption and lipolysaccharide-mediated activation of NFKB. May produce superoxide in the nucleus and play a role in regulating gene expression upon cell stimulation. Isoform 3 is not functional. Isoform 5 and isoform 6 display reduced activity.Isoform 4: Involved in redox signaling in vascular cells. Constitutively and NADPH-dependently generates reactive oxygen species (ROS). Modulates the nuclear activation of ERK1/2 and the ELK1 transcription factor, and is capable of inducing nuclear DNA damage. Displays an increased activity relative to isoform 1.
- Gene Name:
- NOX4
- Uniprot ID:
- Q9NPH5
- Molecular Weight:
- 66930.995 Da
References
- Young GH, Wu VC: KLOTHO methylation is linked to uremic toxins and chronic kidney disease. Kidney Int. 2012 Apr;81(7):611-2. doi: 10.1038/ki.2011.461. [22419041 ]
- General Function:
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function:
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
- Gene Name:
- SLC22A8
- Uniprot ID:
- Q8TCC7
- Molecular Weight:
- 59855.585 Da
References
- Young GH, Wu VC: KLOTHO methylation is linked to uremic toxins and chronic kidney disease. Kidney Int. 2012 Apr;81(7):611-2. doi: 10.1038/ki.2011.461. [22419041 ]
From T3DB