You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2012-09-06 20:58:49 UTC
Update Date2017-09-22 03:01:14 UTC
HMDB IDHMDB0028680
Secondary Accession Numbers
  • HMDB28680
Metabolite Identification
Common NameAlanyl-Alanine
DescriptionAlanyl-Alanine is a dipeptide composed of two alanine residues. 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
Thumb
Synonyms
ValueSource
2-[(2-Ammoniopropanoyl)amino]propanoateChEMBL
2-[(2-Ammoniopropanoyl)amino]propanoic acidGenerator
a-a DipeptideHMDB
AA dipeptideHMDB
Ala-alaHMDB
Alanine alanine dipeptideHMDB
Alanine-alanine dipeptideHMDB
AlanylalanineHMDB
L-Alanyl-L-alanineHMDB
Alanylalanine, (L)-isomerMeSH
Alanylalanine, (L-ala)-(DL-ala)-isomerMeSH
Alanylalanine, (D-ala)-(L-ala)-isomerMeSH
D-Ala-D-alaMeSH
H-Ala-ala-OHMeSH
Alanylalanine, (D)-isomerMeSH
Alanylalanine, (L-ala)-(D-ala)-isomerMeSH
DialanineMeSH
Chemical FormulaC6H12N2O3
Average Molecular Weight160.1711
Monoisotopic Molecular Weight160.08479226
IUPAC Name2-[(2-amino-1-hydroxypropylidene)amino]propanoic acid
Traditional Name2-[(2-amino-1-hydroxypropylidene)amino]propanoic acid
CAS Registry NumberNot Available
SMILES
CC(N)C(O)=NC(C)C(O)=O
InChI Identifier
InChI=1S/C6H12N2O3/c1-3(7)5(9)8-4(2)6(10)11/h3-4H,7H2,1-2H3,(H,8,9)(H,10,11)
InChI KeyDEFJQIDDEAULHB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alanine or derivatives
  • Alpha-amino acid or derivatives
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Primary amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.38Extrapolated
Predicted Properties
PropertyValueSource
Water Solubility70.7 mg/mLALOGPS
logP-2.7ALOGPS
logP-2.7ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.03ChemAxon
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.91 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.32 m3·mol-1ChemAxon
Polarizability15.85 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0f79-0900000000-5d9afc4a11f868ffd54eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014i-0900000000-8c6c90ec8315f93e4ad4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0296-6900000000-4a2353b0310c4ebbfc5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-2fbbf7d129aa1ff9b860View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-222a26c15f778c8576c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2900000000-22675245f5753ab2d4cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059l-9600000000-da5da39743b8a1b6ad4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-9000000000-104a452b2c115fbf2b09View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0028680
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cha MH, Kim KS, Suh D, Yoon Y: Effects of genetic polymorphism of uncoupling protein 2 on body fat and calorie restriction-induced changes. Hereditas. 2007 Nov;144(5):222-7. [PubMed:18031357 ]
  2. Seiderer J, Dambacher J, Leistner D, Tillack C, Glas J, Niess JH, Pfennig S, Jurgens M, Muller-Myhsok B, Goke B, Ochsenkuhn T, Lohse P, Reinecker HC, Brand S: Genotype-phenotype analysis of the CXCL16 p.Ala181Val polymorphism in inflammatory bowel disease. Clin Immunol. 2008 Apr;127(1):49-55. doi: 10.1016/j.clim.2007.11.016. Epub 2008 Jan 11. [PubMed:18248772 ]
  3. Wang P, Wesdemiotis C, Kapota C, Ohanessian G: The sodium ion affinities of simple di-, tri-, and tetrapeptides. J Am Soc Mass Spectrom. 2007 Mar;18(3):541-52. Epub 2006 Dec 8. [PubMed:17157529 ]
  4. Vellaisamy K, Napoleon JV, Venkatachalam R, Manheri MK: Multi-chelation approach towards natural product-like skeletons: one-pot access to a nitrogen-containing tetracyclic framework from AlaAla dipeptide. Chem Commun (Camb). 2010 Dec 28;46(48):9212-4. doi: 10.1039/c0cc03355c. Epub 2010 Oct 28. [PubMed:20981384 ]
  5. Goptar' IA, Kulemzina IA, Filippova IIu, Lysogorskaia EN, Oksenoit ES, Zhuzhikov DP, Dunaevskii IaE, Belozerskii MA, Elpidina EN: [Properties of post-proline cleaving enzymes from Tenebrio molitor]. Bioorg Khim. 2008 May-Jun;34(3):310-6. [PubMed:18672677 ]
  6. Mallone R, Nepom GT: Targeting T lymphocytes for immune monitoring and intervention in autoimmune diabetes. Am J Ther. 2005 Nov-Dec;12(6):534-50. [PubMed:16280647 ]
  7. Dunbar RC, Steill JD, Polfer NC, Oomens J: Peptide length, steric effects, and ion solvation govern zwitterion stabilization in barium-chelated di- and tripeptides. J Phys Chem B. 2009 Aug 6;113(31):10552-4. doi: 10.1021/jp905060n. [PubMed:19606889 ]
  8. Smith MW, Tyreman DR, Payne GM, Marshall NJ, Payne JW: Substrate specificity of the periplasmic dipeptide-binding protein from Escherichia coli: experimental basis for the design of peptide prodrugs. Microbiology. 1999 Oct;145 ( Pt 10):2891-901. [PubMed:10537211 ]