| Common Name |
Phenylalanyl-Serine
| Description |
Phenylalanyl-Serine is a dipeptide composed of phenylalanine and serine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an Expected metabolite.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB29004 (Phenylalanyl-Serine)
| Synonyms |
| Value |
Source |
F-S DipeptideHMDB
FS DipeptideHMDB
L-Phenylalanyl-L-serineHMDB
Phe-serHMDB
Phenylalanine serine dipeptideHMDB
Phenylalanine-serine dipeptideHMDB
PhenylalanylserineHMDB
| Chemical Formlia |
C12H16N2O4
| Average Molecliar Weight |
252.2664
| Monoisotopic Molecliar Weight |
252.11100701
| IUPAC Name |
2-(2-amino-3-phenylpropanamido)-3-hydroxypropanoic acid
| Traditional Name |
2-(2-amino-3-phenylpropanamido)-3-hydroxypropanoic acid
| CAS Registry Number |
Not Available
| SMILES |
NC(CC1=CC=CC=C1)C(=O)NC(CO)C(O)=O
| InChI Identifier |
InChI=1S/C12H16N2O4/c13-9(6-8-4-2-1-3-5-8)11(16)14-10(7-15)12(17)18/h1-5,9-10,15H,6-7,13H2,(H,14,16)(H,17,18)
| InChI Key |
ROHDXJUFQVRDAV-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Carboxylic acids and derivatives
| Direct Parent |
Dipeptides
| Alternative Parents |
Phenylalanine and derivatives
N-acyl-alpha amino acids
Serine and derivatives
Alpha amino acid amides
Amphetamines and derivatives
Aralkylamines
Beta hydroxy acids and derivatives
Fatty amides
Secondary carboxylic acid amides
Amino acids
Monocarboxylic acids and derivatives
Carboxylic acids
Carbonyl compounds
Hydrocarbon derivatives
Monoalkylamines
Organic oxides
Organopnictogen compounds
Primary alcohols
| Substituents |
Alpha-dipeptide
Phenylalanine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Serine or derivatives
Alpha-amino acid or derivatives
Amphetamine or derivatives
Beta-hydroxy acid
Aralkylamine
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Fatty amide
Hydroxy acid
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Alcohol
Primary alcohol
Organopnictogen compound
Primary amine
Amine
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.77Extrapolated
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility3.89 mg/mLALOGPS
logP-2.1ALOGPS
logP-2.8ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)8.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area112.65 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.96 m3·mol-1ChemAxon
Polarizability25.72 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Not Available
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
Not Available
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29004
| Metagene Link |
HMDB29004
| METLIN ID |
Not Available
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Fluorescein-5-maleimide
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Mizuma T, Narasaka T, Awazu S: Uptake of cyclic dipeptide by PEPT1 in Caco-2 cells: phenolic hydroxyl group of substrate enhances affinity for PEPT1. J Pharm Pharmacol. 2002 Sep;54(9):1293-6. [PubMed:12356285 ]
- Mizuma T, Narasaka T, Awazu S: Concentration-dependent atypical intestinal absorption of cyclic phenylalanylserine: small intestine acts as an interface between the body and ingested compounds. Biol Pharm Bull. 2003 Nov;26(11):1625-8. [PubMed:14600416 ]
- Schwarz A, Steinke D, Kula MR, Wandrey C: Optimization of enzyme-mediated peptide bond formation. Biotechnol Appl Biochem. 1990 Apr;12(2):188-95. [PubMed:2109983 ]
- Behling RA, Fischer AG: Formation of phenylalanylserine and cyclo-phenylalanylseryl by protoplasts of Gliocladium virens. Int J Biochem. 1980;11(5):457-8. [PubMed:6156101 ]
- Bucevic-Popovic V, Pavela-Vrancic M, Dieckmann R, Von Dohren H: Relationship between activating and editing functions of the adenylation domain of apo-tyrocidin synthetase 1 (apo-TY1). Biochimie. 2006 Mar-Apr;88(3-4):265-70. Epub 2005 Sep 15. [PubMed:16182433 ]
- Mizuma T, Narasaka T, Hiyoshi W, Awazu S: Concentration-dependent preferences of absorptive and excretive transport cause atypical intestinal absorption of cyclic phenylalanylserine: small intestine acts as an interface between the body and ingested compounds. Res Commun Mol Pathol Pharmacol. 2002;111(5-6):199-209. [PubMed:15244036 ]
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PMID: 17059817