ChemFOnt: Showing chemical card for D-Alanyl-D-alanine (CFc000001897)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:38 UTC

Chemfont ID

CFc000001897

Molecule Identification

Common Name

D-Alanyl-D-alanine

Definition

The ATP-dependent carboxylate-amine/thiol ligase superfamily is known to contain enzymes catalyzing the formation of various types of peptide, one of which is d-alanyl-d-alanine.(PMID: 16030213 ). The glycopeptide antibiotic vancomycin acts by binding to the D-alanyl-D-alanine terminus of the cell wall precursor lipid II in the cytoplasmic membrane.(PMID: 17418637 ). D-alanine-D-alanine ligase from Thermotoga maritima ATCC 43589 (TmDdl) was a useful biocatalyst for synthesizing D-amino acid dipeptides.D-Alanine-D-alanine ligase (Ddl) catalyzes the biosynthesis of an essential bacterial peptidoglycan precursor D-alanyl-D-alanine and it represents an important target for development of new antibacterial drugs. (PMID: 17267218 ). D-Alanyl-D-alanine is a microbial metabolite.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-[(2-Ammoniopropanoyl)amino]propanoate	HMDB
2-[(2-Ammoniopropanoyl)amino]propanoic acid	HMDB
a-a Dipeptide	HMDB
AA dipeptide	HMDB
Ala-ala	HMDB
Alanine alanine dipeptide	HMDB
Alanine-alanine dipeptide	HMDB
Alanylalanine	HMDB
L-Alanyl-L-alanine	HMDB
Alanylalanine, (L)-isomer	HMDB
Alanylalanine, (L-ala)-(DL-ala)-isomer	HMDB
Alanylalanine, (D-ala)-(L-ala)-isomer	HMDB
D-Ala-D-ala	HMDB
H-Ala-ala-OH	HMDB
Alanylalanine, (D)-isomer	HMDB
Alanylalanine, (L-ala)-(D-ala)-isomer	HMDB
Dialanine	HMDB
D-Alanyl-L-alanine	MeSH
D-Alanylalanine	MeSH
H-D-Ala-D-ala-OH	MeSH
L-Alanyl-D-alanine	MeSH
N-D-Alanyl-L-alanine	MeSH
N-L-Alanyl-D-alanine	MeSH
Alanyl-D-alanine	MeSH
Di-L-alanine	MeSH

Chemical Formula

C₆H₁₂N₂O₃

Average Molecular Weight

160.1711

Monoisotopic Molecular Weight

160.08479226

IUPAC Name

2-[(2-amino-1-hydroxypropylidene)amino]propanoic acid

Traditional Name

2-[(2-amino-1-hydroxypropylidene)amino]propanoic acid

CAS Registry Number

923-16-0

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 Key

DEFJQIDDEAULHB-UHFFFAOYSA-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
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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Prostate Tissue (PMID: 19212411)
Saliva (PMID: 22308371)

Cellular substructure

Cytoplasm (HMDB: HMDB0003459)

Source

Exogenous

Exogenous (HMDB: HMDB0003459)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Cereal and cereal product

Cereal

Rice (FooDB: FOOD00125)

Endogenous

Endogenous (HMDB: HMDB0003459)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

D-Alanine Metabolism (PathBank: SMP0121264)
Peptidoglycan Biosynthesis II (PathBank: SMP0122239)
Peptidoglycan Biosynthesis I (PathBank: SMP0121305)
L-Alanine Metabolism (PathBank: SMP0121272)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	10.4 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-2.8	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.32 m³·mol⁻¹	ChemAxon
Polarizability	15.85 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

External Links

HMDB ID

HMDB0246213

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006399

KNApSAcK ID

C00052800

Chemspider ID

581

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

601

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Neuhaus, Francis C. Enzymic synthesis of D-alanyl-D-alanine. Biochemical and Biophysical Research Communications (1960), 3 401-5.

Showing chemical card for D-Alanyl-D-alanine (CFc000001897)

MOL for CFc000001897 (D-Alanyl-D-alanine)

3D MOL for CFc000001897 (D-Alanyl-D-alanine)

3D SDF for CFc000001897 (D-Alanyl-D-alanine)

3D-SDF for CFc000001897 (D-Alanyl-D-alanine)

PDB for CFc000001897 (D-Alanyl-D-alanine)

3D PDB for CFc000001897 (D-Alanyl-D-alanine)

SMILES for CFc000001897 (D-Alanyl-D-alanine)

INCHI for CFc000001897 (D-Alanyl-D-alanine)

Structure for CFc000001897 (D-Alanyl-D-alanine)

3D Structure for CFc000001897 (D-Alanyl-D-alanine)