2-OXO-3-PHENYLPROPIONIC ACID
Relevant Data
Food Additives Approved in the United States
Flavouring Substances Approved by European Union:
General Information
| Synonyms: | 3-PHENYLPYRUVIC ACID |
| Chemical Names: | 2-OXO-3-PHENYLPROPIONIC ACID |
| CAS number: | 156-06-9 |
| JECFA number: | 1479 |
| FEMA number: | 3892 |
| Functional Class: |
Flavouring Agent FLAVOURING_AGENT |
From apps.who.int
Evaluations
| Evaluation year: | 2008 |
| ADI: | No safety concern at current levels of intake when used as a flavouring agent |
| Meeting: | 69 |
| Specs Code: | S |
| Report: | RS 952-JECFA 69/152 |
| Tox Monograph: | FAS 60-JECFA 69/629 |
| Specification: | FAO JECFA Monographs 5/135 |
From apps.who.int
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 997 |
| IUPAC Name | 2-oxo-3-phenylpropanoic acid |
| InChI | InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12) |
| InChI Key | BTNMPGBKDVTSJY-UHFFFAOYSA-N |
| Canonical SMILES | C1=CC=C(C=C1)CC(=O)C(=O)O |
| Molecular Formula | C9H8O3 |
| Wikipedia | phenylpyruvic acid |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 164.16 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 180.0 |
| 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 A w C I A A A g C I A q D S C A I C A A A g A A A I i A F A A I g I I D K A F R C A Y A A k g A A 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 | 54.4 |
| Monoisotopic Mass | 164.047 |
| Exact Mass | 164.047 |
| XLogP3 | None |
| XLogP3-AA | 1.3 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 12 |
| 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+ | 0.9392 |
| Human Intestinal Absorption | HIA+ | 0.9766 |
| Caco-2 Permeability | Caco2+ | 0.6174 |
| P-glycoprotein Substrate | Non-substrate | 0.7968 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9230 |
| Non-inhibitor | 0.9587 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9110 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8950 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8472 |
| CYP450 2D6 Substrate | Non-substrate | 0.9420 |
| CYP450 3A4 Substrate | Non-substrate | 0.8014 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9261 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9569 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9636 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9673 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9811 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9827 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9751 |
| Non-inhibitor | 0.9729 | |
| AMES Toxicity | Non AMES toxic | 0.8852 |
| Carcinogens | Non-carcinogens | 0.7818 |
| Fish Toxicity | High FHMT | 0.6407 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8778 |
| Honey Bee Toxicity | High HBT | 0.6264 |
| Biodegradation | Ready biodegradable | 0.9150 |
| Acute Oral Toxicity | III | 0.5569 |
| Carcinogenicity (Three-class) | Non-required | 0.7302 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.8882 | LogS |
| Caco-2 Permeability | 0.8760 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.7408 | LD50, mol/kg |
| Fish Toxicity | 1.8953 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.4788 | pIGC50, ug/L |
From admetSAR
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Phenylpyruvic acid derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenylpyruvic acid derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenylpyruvate - 3-phenylpropanoic-acid - Keto acid - Alpha-keto acid - Alpha-hydroxy ketone - Ketone - 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 phenylpyruvic acid derivatives. These are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. |
From ClassyFire
Targets
- General Function:
- Phenylalanine dehydrogenase activity
- Specific Function:
- Catalyzes the reversible, NAD-dependent deamination of L-phenylalanine to phenyl pyruvate, ammonia and NADH.
- Gene Name:
- pdh
- Uniprot ID:
- Q59771
- Molecular Weight:
- 36608.615 Da
- General Function:
- Very-long-chain-(s)-2-hydroxy-acid oxidase activity
- Specific Function:
- Has 2-hydroxyacid oxidase activity. Most active on the 2-carbon substrate glycolate, but is also active on 2-hydroxy fatty acids, with high activity towards 2-hydroxy palmitate and 2-hydroxy octanoate.
- Gene Name:
- HAO1
- Uniprot ID:
- Q9UJM8
- Molecular Weight:
- 40923.945 Da
- General Function:
- Thiamine pyrophosphate binding
- Gene Name:
- ipdC
- Uniprot ID:
- P51852
- Molecular Weight:
- 57979.97 Da
- Uniprot ID:
- Q7NSZ5
- Molecular Weight:
- 21777.22 Da
- Specific Function:
- Part of the bacABCDE operon responsible for the biosynthesis of bacilysin.
- Gene Name:
- bacB
- Uniprot ID:
- P39639
- Molecular Weight:
- 26839.49 Da
- General Function:
- Prephenate dehydratase activity
- Gene Name:
- pheA
- Uniprot ID:
- A1A2B5
- Molecular Weight:
- 35784.095 Da
From T3DB