CHEBI:15570 - D-alanine

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ChEBI Name D-alanine
ChEBI ID CHEBI:15570
ChEBI ASCII Name D-alanine
Definition The D-enantiomer of alanine.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:10840, CHEBI:41848, CHEBI:41756, CHEBI:41877, CHEBI:41798, CHEBI:4087, CHEBI:20893, CHEBI:12899
Supplier Information ChemicalBook:CB7783360, eMolecules:476062, ZINC000004658556
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Formula C3H7NO2
Net Charge 0
Average Mass 89.09322
Monoisotopic Mass 89.04768
InChI InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1
InChIKey QNAYBMKLOCPYGJ-UWTATZPHSA-N
SMILES C[C@@H](N)C(O)=O
Metabolite of Species Details
Escherichia coli (NCBI:txid562) See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor
An EC 4.3.1.* (ammonia-lyase) inhibitor that interferes with the action of diaminopropionate ammonia-lyase (EC 4.3.1.15).
fundamental metabolite
Any metabolite produced by all living cells.
(via alanine )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing D-alanine (CHEBI:15570) has role Escherichia coli metabolite (CHEBI:76971)
D-alanine (CHEBI:15570) has role EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor (CHEBI:77881)
D-alanine (CHEBI:15570) has role human metabolite (CHEBI:77746)
D-alanine (CHEBI:15570) is a D-α-amino acid (CHEBI:16733)
D-alanine (CHEBI:15570) is a alanine (CHEBI:16449)
D-alanine (CHEBI:15570) is conjugate acid of D-alaninate (CHEBI:32435)
D-alanine (CHEBI:15570) is conjugate base of D-alaninium (CHEBI:32436)
D-alanine (CHEBI:15570) is enantiomer of L-alanine (CHEBI:16977)
D-alanine (CHEBI:15570) is tautomer of D-alanine zwitterion (CHEBI:57416)
Incoming β-(2-thienyl)-D-alanine (CHEBI:77819) has functional parent D-alanine (CHEBI:15570)
D-alanine derivative (CHEBI:83944) has functional parent D-alanine (CHEBI:15570)
D-lupinic acid (CHEBI:30886) has functional parent D-alanine (CHEBI:15570)
fusarithioamide A (CHEBI:141359) has functional parent D-alanine (CHEBI:15570)
metalaxyl-M (CHEBI:60607) has functional parent D-alanine (CHEBI:15570)
pradimicin A (CHEBI:8349) has functional parent D-alanine (CHEBI:15570)
pradimicin B (CHEBI:8350) has functional parent D-alanine (CHEBI:15570)
pradimicin C (CHEBI:8351) has functional parent D-alanine (CHEBI:15570)
D-alaninium (CHEBI:32436) is conjugate acid of D-alanine (CHEBI:15570)
D-alaninate (CHEBI:32435) is conjugate base of D-alanine (CHEBI:15570)
L-alanine (CHEBI:16977) is enantiomer of D-alanine (CHEBI:15570)
D-alanine residue (CHEBI:29949) is substituent group from D-alanine (CHEBI:15570)
D-alanino group (CHEBI:32438) is substituent group from D-alanine (CHEBI:15570)
D-alanyl group (CHEBI:32437) is substituent group from D-alanine (CHEBI:15570)
D-alanine zwitterion (CHEBI:57416) is tautomer of D-alanine (CHEBI:15570)
IUPAC Name
D-alanine
Synonyms Sources
(2R)-2-aminopropanoic acid IUPAC
(R)-2-aminopropanoic acid ChEBI
(R)-alanine NIST Chemistry WebBook
D-2-Aminopropionic acid KEGG COMPOUND
D-Ala KEGG COMPOUND
D-Alanin ChEBI
D-Alanine KEGG COMPOUND
D-α-alanine NIST Chemistry WebBook
D-α-aminopropionic acid ChEBI
DAL PDBeChem
Manual Xrefs Databases
C00019654 KNApSAcK
C00133 KEGG COMPOUND
D-ALANINE MetaCyc
DAL PDBeChem
DB01786 DrugBank
ECMDB01310 ECMDB
HMDB0001310 HMDB
YMDB00993 YMDB
View more database links
Registry Numbers Types Sources
1720249 Reaxys Registry Number Reaxys
338-69-2 CAS Registry Number KEGG COMPOUND
338-69-2 CAS Registry Number ChemIDplus
338-69-2 CAS Registry Number NIST Chemistry WebBook
82157 Gmelin Registry Number Gmelin
Citations
Marui J, Matsushita-Morita M, Tada S, Hattori R, Suzuki S, Amano H, Ishida H, Yamagata Y, Takeuchi M, Kusumoto K (2012)
Enzymatic properties of the glycine D-alanine [corrected] aminopeptidase of Aspergillus oryzae and its activity profiles in liquid-cultured mycelia and solid-state rice culture (rice koji).
Applied microbiology and biotechnology 93, 655-669 [PubMed:22005737]
[show Abstract]
Miyauchi E, Morita M, Rossi M, Morita H, Suzuki T, Tanabe S (2012)
Effect of D-alanine in teichoic acid from the Streptococcus thermophilus cell wall on the barrier-protection of intestinal epithelial cells.
Bioscience, biotechnology, and biochemistry 76, 283-288 [PubMed:22313760]
[show Abstract]
Suda S, Lawton EM, Wistuba D, Cotter PD, Hill C, Ross RP (2012)
Homologues and bioengineered derivatives of LtnJ vary in ability to form D-alanine in the lantibiotic lacticin 3147.
Journal of bacteriology 194, 708-714 [PubMed:22123251]
[show Abstract]
Awasthy D, Bharath S, Subbulakshmi V, Sharma U (2012)
Alanine racemase mutants of Mycobacterium tuberculosis require D-alanine for growth and are defective for survival in macrophages and mice.
Microbiology (Reading, England) 158, 319-327 [PubMed:22075031]
[show Abstract]
Strych U, Huang HC, Krause KL, Benedik MJ (2000)
Characterization of the alanine racemases from Pseudomonas aeruginosa PAO1.
Current microbiology 41, 290-294 [PubMed:10977898]
[show Abstract]
D'Aniello A, Vetere A, Fisher GH, Cusano G, Chavez M, Petrucelli L (1992)
Presence of D-alanine in proteins of normal and Alzheimer human brain.
Brain research 592, 44-48 [PubMed:1450921]
[show Abstract]
Nagasawa T, Tanizawa K, Satoda T, Yamada H (1988)
Diaminopropionate ammonia-lyase from Salmonella typhimurium. Purification and characterization of the crystalline enzyme, and sequence determination of the pyridoxal 5'-phosphate binding peptide.
The Journal of biological chemistry 263, 958-964 [PubMed:3275662]
[show Abstract]
Last Modified
15 August 2018