MiMeDB: Showing metabocard for Alanylalanine (MMDBc0000269)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:48:13 UTC

Update Date

2024-04-30 19:31:44 UTC

Metabolite ID

MMDBc0000269

Metabolite Identification

Common Name

Alanylalanine

Description

Alanylalanine 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
AA	ChEBI
Ala-ala	ChEBI
L-Ala-L-ala	ChEBI
N-L-Alanyl-L-alanine	ChEBI
Alanylalanine, (D-ala)-(L-ala)-isomer	MeSH, HMDB
Alanylalanine, (L-ala)-(D-ala)-isomer	MeSH, HMDB
Dialanine	MeSH, HMDB
D-Ala-D-ala	MeSH, HMDB
H-Ala-ala-OH	MeSH, HMDB
Alanylalanine, (D)-isomer	MeSH, HMDB
Alanylalanine, (L)-isomer	MeSH, HMDB
Alanylalanine, (L-ala)-(DL-ala)-isomer	MeSH, HMDB
Alanylalanine	MeSH
N-D-Alanyl-L-alanine	MeSH, HMDB
N-L-Alanyl-D-alanine	MeSH, HMDB
H-D-Ala-D-ala-OH	MeSH, HMDB
Alanyl-D-alanine	MeSH, HMDB
Di-L-alanine	MeSH, HMDB
D-Alanyl-D-alanine	MeSH, HMDB
D-Alanylalanine	MeSH, HMDB
D-Alanyl-L-alanine	MeSH, HMDB
L-Alanyl-D-alanine	MeSH, HMDB
A-A dipeptide	HMDB
AA dipeptide	HMDB
Alanine alanine dipeptide	HMDB
Alanine-alanine dipeptide	HMDB
Alanyl-alanine	HMDB
L-Alanyl-L-alanine	HMDB
N-Alanylalanine	HMDB
NSC 89598	HMDB
alpha-Alanylalanine	HMDB
α-Alanylalanine	HMDB

Molecular Formula

C₆H₁₂N₂O₃

Average Mass

160.1711

Monoisotopic Mass

160.08479226

IUPAC Name

(2S)-2-[(2S)-2-aminopropanamido]propanoic acid

Traditional Name

(2S)-2-[(2S)-2-aminopropanamido]propanoic acid

CAS Registry Number

1948-31-8

SMILES

C[C@H](N)C(=O)N[C@@H](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)/t3-,4-/m0/s1

InChI Key

DEFJQIDDEAULHB-IMJSIDKUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
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
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dipeptide (CHEBI:72816 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	70.7 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-3.4	ChemAxon
logS	-0.36	ALOGPS
pKa (Strongest Acidic)	3.73	ChemAxon
pKa (Strongest Basic)	8.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.42 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	37.79 m³·mol⁻¹	ChemAxon
Polarizability	15.52 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0fga-9800000000-0bf53db242afda4f5358	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-014i-0900000000-b900eb23a067d3da2dab	2014-06-16	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Negative	splash10-0a4i-1900000000-98d9275f2b3eea103b4a	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0006-9100000000-e7365ff586d713020d66	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0296-4900000000-20846dc82978c9ddade4	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-1271c8457df1a569480e	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9000000000-f584320f1e3633c2e808	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-8ed3744b20a8eefee5b6	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-059i-9600000000-b064bf4d540d9047af3a	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00du-9000000000-ea85ea32680736b18092	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9100000000-a9556cdd03ea097d9213	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-2cbbf675159b82ddf5e8	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-ac3751498e9cf095d11f	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052o-4900000000-aae09911d82d8cfafc1f	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9100000000-fcc1d4e4f5652338825f	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-f5f0d3e84942d47714c6	2021-10-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	2	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool
Bacteria	Actinobacteria	1	Human

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050

External Links

HMDB ID

HMDB0028680

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003740

KNApSAcK ID

C00017958

Chemspider ID

4588478

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5484352

PDB ID

Not Available

ChEBI ID

72816

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 (Reading). 1999 Oct;145 ( Pt 10):2891-901. doi: 10.1099/00221287-145-10-2891. [PubMed:10537211 ]
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. doi: 10.1097/01.mjt.0000178772.54396.38. [PubMed:16280647 ]
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. doi: 10.1016/j.jasms.2006.10.024. Epub 2006 Dec 8. [PubMed:17157529 ]
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. doi: 10.1111/j.2007.0018-0661.02005.x. [PubMed:18031357 ]
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 ]
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. doi: 10.1134/s1068162008030047. [PubMed:18672677 ]
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 ]
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 ]

Showing metabocard for Alanylalanine (MMDBc0000269)

MOL for #<Metabolite:0x00007fdb59156418>

3D MOL for #<Metabolite:0x00007fdb59156418>

3D SDF for #<Metabolite:0x00007fdb59156418>

3D-SDF for #<Metabolite:0x00007fdb59156418>

PDB for #<Metabolite:0x00007fdb59156418>

3D PDB for #<Metabolite:0x00007fdb59156418>

SMILES for #<Metabolite:0x00007fdb59156418>

INCHI for #<Metabolite:0x00007fdb59156418>

Structure for #<Metabolite:0x00007fdb59156418>

3D Structure for #<Metabolite:0x00007fdb59156418>