| Common Name |
Tryptophyl-Alanine
| Description |
Tryptophyl-Alanine is a dipeptide composed of tryptophan and alanine. 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 HMDB29076 (Tryptophyl-Alanine)
| Synonyms |
| Value |
Source |
L-Tryptophyl-L-alanineHMDB
TRP-AlaHMDB
Tryptophan alanine dipeptideHMDB
Tryptophan-alanine dipeptideHMDB
TryptophylalanineHMDB
W-a DipeptideHMDB
WA dipeptideHMDB
| Chemical Formlia |
C14H17N3O3
| Average Molecliar Weight |
275.3031
| Monoisotopic Molecliar Weight |
275.126991425
| IUPAC Name |
2-[2-amino-3-(1H-indol-3-yl)propanamido]propanoic acid
| Traditional Name |
trp-ala
| CAS Registry Number |
Not Available
| SMILES |
CC(NC(=O)C(N)CC1=CNC2=C1C=CC=C2)C(O)=O
| InChI Identifier |
InChI=1S/C14H17N3O3/c1-8(14(19)20)17-13(18)11(15)6-9-7-16-12-5-3-2-4-10(9)12/h2-5,7-8,11,16H,6,15H2,1H3,(H,17,18)(H,19,20)
| InChI Key |
OHGNSVACHBZKSS-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 |
N-acyl-alpha amino acids
Tryptamines and derivatives
Alpha amino acid amides
Alanine and derivatives
3-alkylindoles
Aralkylamines
Substituted pyrroles
Fatty amides
Benzenoids
Heteroaromatic compounds
Secondary carboxylic acid amides
Amino acids
Monocarboxylic acids and derivatives
Azacyclic compounds
Carboxylic acids
Hydrocarbon derivatives
Monoalkylamines
Organic oxides
Organopnictogen compounds
Carbonyl compounds
| Substituents |
Alpha-dipeptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Triptan
Alanine or derivatives
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Fatty amide
Substituted pyrrole
Fatty acyl
Benzenoid
Heteroaromatic compound
Pyrrole
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Amino acid
Organoheterocyclic compound
Azacycle
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organooxygen compound
Amine
Primary amine
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic 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-1.62Extrapolated
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.68 mg/mLALOGPS
logP-0.88ALOGPS
logP-1.6ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)7.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area108.21 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.5 m3·mol-1ChemAxon
Polarizability28.67 Å3ChemAxon
Number of Rings2ChemAxon
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 |
HMDB29076
| Metagene Link |
HMDB29076
| METLIN ID |
Not Available
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: MX69
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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 ]
- Kano K, Hasegawa H, Miyamura M: Chiral recognition of dipeptide methyl esters by an anionic beta-cyclodextrin. Chirality. 2001 Aug;13(8):474-82. [PubMed:11466771 ]
- Fleming GR, Morris JM, Robbins RJ, Woolfe GJ, Thistlethwaite PJ, Robinson GW: Nonexponential fluorescence decay of aqueous tryptophan and two related peptides by picosecond spectroscopy. Proc Natl Acad Sci U S A. 1978 Oct;75(10):4652-6. [PubMed:16592569 ]
- Joshi S, Ghosh I, Pokhrel S, Madler L, Nau WM: Interactions of amino acids and polypeptides with metal oxide nanoparticles probed by fluorescent indicator adsorption and displacement. ACS Nano. 2012 Jun 26;6(6):5668-79. doi: 10.1021/nn301669t. Epub 2012 May 22. [PubMed:22591378 ]
|
PMID: 22917617
