| Common Name |
Glycyl-Phenylalanine
| Description |
Glycyl-Phenylalanine is a dipeptide composed of glycine and phenylalanine. 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 HMDB28848 (Glycyl-Phenylalanine)
| Synonyms |
| Value |
Source |
g-F DipeptideHMDB
GF DipeptideHMDB
Gly-pheHMDB
Glycine phenylalanine dipeptideHMDB
Glycine-phenylalanine dipeptideHMDB
GlycylphenylalanineHMDB
L-Glycyl-L-phenylalanineHMDB
Gly-D-phenylalanineMeSH
Glycyl-D-phenylalanineMeSH
Glycylphenylalanine, (L)-isomerMeSH
Glycylphenylalanine, (D)-isomerMeSH
Gly-L-phenylalanineMeSH
Glycyl-L-phenylalanineMeSH
Glycylphenylalanine monobrosylate, (L)-isomerMeSH
Glycylphenylalanine monohydrochloride, monohydrate, (L)-isomerMeSH
Glycylphenylalanine monotosylate, (L)-isomerMeSH
| Chemical Formlia |
C11H14N2O3
| Average Molecliar Weight |
222.2405
| Monoisotopic Molecliar Weight |
222.100442324
| IUPAC Name |
2-(2-aminoacetamido)-3-phenylpropanoic acid
| Traditional Name |
2-(2-aminoacetamido)-3-phenylpropanoic acid
| CAS Registry Number |
Not Available
| SMILES |
NCC(=O)NC(CC1=CC=CC=C1)C(O)=O
| InChI Identifier |
InChI=1S/C11H14N2O3/c12-7-10(14)13-9(11(15)16)6-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,14)(H,15,16)
| InChI Key |
JBCLFWXMTIKCCB-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
Alpha amino acid amides
Phenylpropanoic acids
Amphetamines and derivatives
Secondary carboxylic acid amides
Amino acids
Monocarboxylic acids and derivatives
Carboxylic acids
Organopnictogen compounds
Organic oxides
Monoalkylamines
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Alpha-dipeptide
Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
3-phenylpropanoic-acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Amino acid
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic homomonocyclic compound
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Detected 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-2.29Extrapolated
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility1.21 mg/mLALOGPS
logP-1.1ALOGPS
logP-2.3ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.73ChemAxon
pKa (Strongest Basic)8.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity57.92 m3·mol-1ChemAxon
Polarizability22.6 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 |
Saliva
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
SalivaDetected but not Quantified Adlit (>18 years old)Male
Normal
22308371
details
|
| 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 |
HMDB28848
| Metagene Link |
HMDB28848
| METLIN ID |
Not Available
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: AK-1
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Rai DK, Mooney A, Kenny PT: A tandem mass spectrometric investigation of N-(3-ferrocenyl-2-naphthoyl) dipeptide ethyl esters and N-(6-ferrocenyl-2-naphthoyl) dipeptide ethyl esters. Rapid Commun Mass Spectrom. 2011 Oct 15;25(19):2905-10. doi: 10.1002/rcm.5184. [PubMed:21913269 ]
- Pingitore F, Wesdemiotis C: Characterization of dipeptide isomers by tandem mass spectrometry of their mono- versus dilithiated complexes. Anal Chem. 2005 Mar 15;77(6):1796-806. [PubMed:15762588 ]
- Girelli AM, Mattei E, Messina A, Tarola AM: Inhibition of polyphenol oxidases activity by various dipeptides. J Agric Food Chem. 2004 May 19;52(10):2741-5. [PubMed:15137808 ]
- Thirumoorthy K, Soni K, Nandi N: The molecular recognition of dipeptide by oligoglycyl head group of amphiphile: a quantum chemical study. J Nanosci Nanotechnol. 2009 Jan;9(1):77-89. [PubMed:19441281 ]
- Turecek F, Syrstad EA, Seymour JL, Chen X, Yao C: Peptide cation-radicals. A computational study of the competition between peptide N-Calpha bond cleavage and loss of the side chain in the [GlyPhe-NH2 + 2H]+. cation-radical. J Mass Spectrom. 2003 Oct;38(10):1093-104. [PubMed:14595859 ]
- Anderson L, Bussler B, Martins H, Dufton M: Enkephalin-processing oligopeptidases in cobra venom: inhibition by thiorphan and bestatin reveals co-operative actions. Toxicon. 1998 May;36(5):719-28. [PubMed:9655632 ]
- Duman JG, Chen L, Palmer AE, Hille B: Contributions of intracellular compartments to calcium dynamics: implicating an acidic store. Traffic. 2006 Jul;7(7):859-72. [PubMed:16787398 ]
- Epand RM: Virus replication inhibitory peptide inhibits the conversion of phospholipid bilayers to the hexagonal phase. Biosci Rep. 1986 Jul;6(7):647-53. [PubMed:3779040 ]
- Lopez JJ, Camello-Almaraz C, Pariente JA, Salido GM, Rosado JA: Ca2+ accumulation into acidic organelles mediated by Ca2+- and vacuolar H+-ATPases in human platelets. Biochem J. 2005 Aug 15;390(Pt 1):243-52. [PubMed:15847604 ]
- Tobin MB, Cole SC, Miller JR, Baldwin JE, Sutherland JD: Amino-acid substitutions in the cleavage site of acyl-coenzyme A:isopenicillin N acyltransferase from Penicillium chrysogenum: effect on proenzyme cleavage and activity. Gene. 1995 Aug 30;162(1):29-35. [PubMed:7557412 ]
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PMID: 9369342