(R)-3-phenyllactic acid
PubChem CID: 643327
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| Compound Synonyms | 7326-19-4, (R)-2-Hydroxy-3-phenylpropionic acid, (R)-2-hydroxy-3-phenylpropanoic acid, D-(+)-3-Phenyllactic acid, (2R)-2-hydroxy-3-phenylpropanoic acid, (R)-3-Phenyllactic acid, D-(+)-Phenyllactic acid, D-3-phenyllactic acid, MFCD00078062, (R)-phenyllactate, 3-Phenyllactic acid, (R)-, 68L11J0XBS, (2R)-2-Hydroxy-3-phenyl-propanoic acid, EINECS 230-803-3, D-?(+)?-?Phenyllactic acid, CHEBI:32978, DTXSID70904708, (R)-(+)-3-Phenyllactic Acid, (+)-2-Hydroxy-3-phenylpropionic acid, (R)-3-(phenyl)lactate, 3-Phenyl-D-lactic acid, L-Phenyl Lactate, (2S)-2-Hydroxy-3-phenylpropionic acid, L-3-Phenyllactate, (s)-b-phenyllactic, l-2-hydroxy-3-phenyl-propionic acid, (-)-b-phenyllactate, (s)-beta-phenyllactic, (-)-3-Phenyllactate, (-)-beta-phenyllactate, (S)-3-phenyl-Lactate, (-)-b-phenyllactic acid, D/L-3-phenyllactic acid, (-)-beta-phenyllactic acid, (S)-3-phenyl-Lactic acid, UNII-68L11J0XBS, SCHEMBL180366, (s)-a-hydroxy-benzenepropanoate, DTXCID301333817, (-)-2-Hydroxy-3-phenylpropanoate, (-)-2-Hydroxy-3-phenylpropionate, (s)-a-hydroxy-benzenepropanoic acid, (s)-alpha-hydroxy-benzenepropanoate, (2S)-2-Hydroxy-3-phenylpropionate, (2R)-hydroxy-3-phenylpropanoic acid, (R)-2-hydroxy-3-phenylpropanoicacid, FD1250, s6326, D-(+)-3-Phenyllactic acid, 98%, AKOS005146076, AKOS016015834, (-)-2-Hydroxy-3-phenylpropanoic acid, (-)-2-Hydroxy-3-phenylpropionic acid, AC-5644, CS-W020670, FP08624, (rac)-2-hydroxy-3-phenylpropionic acid, (s)-alpha-hydroxy-benzenepropanoic acid, DS-14380, HY-30219, DB-031276, (R)-(+)-2-Hydroxy-3-phenylpropionic Acid, NS00081021, P1981, C05607, EN300-116770, Q22574124, Z1255364914, (R)-2-Hydroxy-3-phenylpropionic acid, (R)-3-Phenyllactic acid, 230-803-3 |
|---|---|
| Topological Polar Surface Area | 57.5 |
| Hydrogen Bond Donor Count | 2.0 |
| Heavy Atom Count | 12.0 |
| Description | L-3-Phenyllactic acid (or PLA) is a chiral aromatic compound involved in phenylalanine metabolism. It is likely produced from phenylpyruvate via the action of lactate dehydrogenase. The D-form of this organic acid is typically derived from bacterial sources while the L-form is almost certainly endogenous. Levels of phenyllactate are normally very low in blood or urine. High levels of PLA in the urine or blood are often indicative of phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid (a precursor of phenylactate). In particular, excessive phenylalanine is typically metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid and then to phenyllactate through the action of lactate dehydrogenase. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation), and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. [HMDB] |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 150.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 1.0 |
| Iupac Name | (2R)-2-hydroxy-3-phenylpropanoic acid |
| Prediction Hob | 1.0 |
| Class | Phenylpropanoic acids |
| Xlogp | 1.1 |
| Superclass | Phenylpropanoids and polyketides |
| Molecular Formula | C9H10O3 |
| Prediction Swissadme | 0.0 |
| Inchi Key | VOXXWSYKYCBWHO-MRVPVSSYSA-N |
| Fcsp3 | 0.2222222222222222 |
| Logs | -0.484 |
| Rotatable Bond Count | 3.0 |
| State | Solid |
| Logd | -0.514 |
| Synonyms | (-)-2-Hydroxy-3-phenylpropanoate, (-)-2-Hydroxy-3-phenylpropanoic acid, (-)-2-Hydroxy-3-phenylpropionate, (-)-2-Hydroxy-3-phenylpropionic acid, (-)-3-Phenyllactate, (-)-3-Phenyllactic acid, (-)-b-phenyllactate, (-)-b-phenyllactic acid, (-)-beta-phenyllactate, (-)-beta-phenyllactic acid, (2S)-2-hydroxy-3-phenylpropanoate, (2S)-2-hydroxy-3-phenylpropanoic acid, (2S)-2-Hydroxy-3-phenylpropionate, (2S)-2-Hydroxy-3-phenylpropionic acid, (R)-Phenyllactate, (R)-Phenyllactic acid, (S)-3-phenyl-Lactate, (S)-3-phenyl-Lactic acid, (S)-3-phenyllactic acid, (s)-a-hydroxy-benzenepropanoate, (s)-a-hydroxy-benzenepropanoic acid, (s)-alpha-hydroxy-benzenepropanoate, (s)-alpha-hydroxy-benzenepropanoic acid, (s)-b-phenyllactic, (s)-beta-phenyllactic, Alpha-hydroxy-beta-phenyl-propionic acid, D-3-Phenyllactate, D-3-Phenyllactic acid, HFA, L-(-)-3-phenyllactic acid, L-2-hydroxy-3-phenyl-propionic acid, L-3-Phenyllactate, L-beta-phenyllactic acid, L-phenyl lactate, (R)-3-(Phenyl)lactate, (R)-3-(Phenyl)lactic acid, (-)-b-Phenyllactate, (-)-b-Phenyllactic acid, (-)-beta-Phenyllactate, (-)-beta-Phenyllactic acid, (2S)-2-Hydroxy-3-phenylpropanoate, (2S)-2-Hydroxy-3-phenylpropanoic acid, (S)-3-Phenyl-lactate, (S)-3-Phenyl-lactic acid, (S)-3-Phenyllactic acid, (S)-a-Hydroxy-benzenepropanoate, (S)-a-Hydroxy-benzenepropanoic acid, (S)-alpha-Hydroxy-benzenepropanoate, (S)-alpha-Hydroxy-benzenepropanoic acid, (S)-b-Phenyllactic, (S)-beta-Phenyllactic, alpha-Hydroxy-beta-phenyl-propionic acid, L-(-)-3-Phenyllactic acid, L-2-Hydroxy-3-phenyl-propionic acid, L-beta-Phenyllactic acid, L-Phenyl lactate, Phenyllactic acid, (R)-3-Phenyllactate |
| Compound Name | (R)-3-phenyllactic acid |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 166.063 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 166.063 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 166.17 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 1.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Esol | -1.7541912000000002 |
| Inchi | InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/t8-/m1/s1 |
| Smiles | C1=CC=C(C=C1)C[C@H](C(=O)O)O |
| Nring | 1.0 |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Phenylpropanoic acids |
- 1. Outgoing r'ship
FOUND_INto/from Lysimachia Candida (Plant) Rel Props:Source_db:cmaup_ingredients