D-Alanine
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Identification
- Generic Name
- D-Alanine
- DrugBank Accession Number
- DB01786
- Background
The D-enantiomer of alanine.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 89.0932
Monoisotopic: 89.047678473 - Chemical Formula
- C3H7NO2
- Synonyms
- (2R)-2-aminopropanoic acid
- (R)-2-aminopropanoic acid
- (R)-alanine
- D-2-Aminopropionic acid
- D-Ala
- D-Alanin
- D-α-alanine
- D-α-aminopropionic acid
- DAL
- External IDs
- NSC-158286
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UThermolysin Not Available Geobacillus stearothermophilus UD-alanyl-D-alanine carboxypeptidase Not Available Streptomyces sp. (strain R61) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alanine and derivatives. These are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alanine and derivatives
- Alternative Parents
- D-alpha-amino acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alanine or derivatives / Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Carbonyl group / Carboxylic acid / D-alpha-amino acid / Hydrocarbon derivative / Monocarboxylic acid or derivatives
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- D-alpha-amino acid, alanine (CHEBI:15570) / Other amino acids (C00133)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- E3UDS4613U
- CAS number
- 338-69-2
- InChI Key
- QNAYBMKLOCPYGJ-UWTATZPHSA-N
- InChI
- InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1
- IUPAC Name
- (2R)-2-aminopropanoic acid
- SMILES
- C[C@@H](N)C(O)=O
References
- Synthesis Reference
Donald F. Reinhold, "Process for preparing 3-fluoro-D-alanine and its deutero analogs." U.S. Patent US3976689, issued May, 1963.
US3976689- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001310
- KEGG Compound
- C00133
- PubChem Compound
- 71080
- PubChem Substance
- 46508779
- ChemSpider
- 64234
- BindingDB
- 50000109
- ChEBI
- 15570
- ChEMBL
- CHEMBL66693
- ZINC
- ZINC000004658556
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- DAL
- PDB Entries
- 148l / 1aj1 / 1bck / 1bfw / 1bzv / 1c0p / 1c4b / 1c5f / 1csa / 1cwa … show 388 more
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 292 °C PhysProp water solubility 1.65E+005 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) - Predicted Properties
Property Value Source Water Solubility 447.0 mg/mL ALOGPS logP -3 ALOGPS logP -2.8 Chemaxon logS 0.7 ALOGPS pKa (Strongest Acidic) 2.47 Chemaxon pKa (Strongest Basic) 9.48 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 63.32 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 20.5 m3·mol-1 Chemaxon Polarizability 8.54 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9506 Blood Brain Barrier + 0.6314 Caco-2 permeable - 0.8957 P-glycoprotein substrate Non-substrate 0.8222 P-glycoprotein inhibitor I Non-inhibitor 0.9919 P-glycoprotein inhibitor II Non-inhibitor 0.9952 Renal organic cation transporter Non-inhibitor 0.9644 CYP450 2C9 substrate Non-substrate 0.8125 CYP450 2D6 substrate Non-substrate 0.8851 CYP450 3A4 substrate Non-substrate 0.8204 CYP450 1A2 substrate Non-inhibitor 0.946 CYP450 2C9 inhibitor Non-inhibitor 0.9645 CYP450 2D6 inhibitor Non-inhibitor 0.9748 CYP450 2C19 inhibitor Non-inhibitor 0.9797 CYP450 3A4 inhibitor Non-inhibitor 0.9384 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9938 Ames test Non AMES toxic 0.9339 Carcinogenicity Non-carcinogens 0.62 Biodegradation Ready biodegradable 0.7662 Rat acute toxicity 1.0339 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9891 hERG inhibition (predictor II) Non-inhibitor 0.9841
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 109.0252829 predictedDarkChem Lite v0.1.0 [M-H]- 109.2726829 predictedDarkChem Lite v0.1.0 [M-H]- 109.1101829 predictedDarkChem Lite v0.1.0 [M-H]- 115.22616 predictedDeepCCS 1.0 (2019) [M+H]+ 110.0791829 predictedDarkChem Lite v0.1.0 [M+H]+ 110.3649829 predictedDarkChem Lite v0.1.0 [M+H]+ 109.7369829 predictedDarkChem Lite v0.1.0 [M+H]+ 118.02554 predictedDeepCCS 1.0 (2019) [M+Na]+ 109.2508829 predictedDarkChem Lite v0.1.0 [M+Na]+ 109.4141829 predictedDarkChem Lite v0.1.0 [M+Na]+ 109.0277829 predictedDarkChem Lite v0.1.0 [M+Na]+ 126.461525 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsThermolysin
- Kind
- Protein
- Organism
- Geobacillus stearothermophilus
- Pharmacological action
- Unknown
- General Function
- Extracellular zinc metalloprotease.
- Specific Function
- metal ion binding
- Gene Name
- nprS
- Uniprot ID
- P43133
- Uniprot Name
- Thermolysin
- Molecular Weight
- 60616.22 Da
References
2. DetailsD-alanyl-D-alanine carboxypeptidase
- Kind
- Protein
- Organism
- Streptomyces sp. (strain R61)
- Pharmacological action
- Unknown
- General Function
- Catalyzes distinct carboxypeptidation and transpeptidation reactions during the last stages of wall peptidoglycan synthesis. Mistaking a beta-lactam antibiotic molecule for a normal substrate (i.e. a D-alanyl-D-alanine-terminated peptide), it becomes immobilized in the form of a long-lived, serine-ester-linked acyl enzyme and thus behave as penicillin-binding protein (PBP).
- Specific Function
- serine-type D-Ala-D-Ala carboxypeptidase activity
- Gene Name
- Not Available
- Uniprot ID
- P15555
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase
- Molecular Weight
- 42916.725 Da
References
Transporters
1. DetailsMonocarboxylate transporter 10
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium- and proton-independent thyroid hormones and aromatic acids transporter (PubMed:11827462, PubMed:18337592, PubMed:28754537). Mediates both uptake and efflux of 3,5,3'-triiodothyronine (T3) and 3,5,3',5'-tetraiodothyronine (T4) with high affinity, suggesting a role in the homeostasis of thyroid hormone levels (PubMed:18337592). Responsible for low affinity bidirectional transport of the aromatic amino acids, such as phenylalanine, tyrosine, tryptophan and L-3,4-dihydroxyphenylalanine (L-dopa) (PubMed:11827462, PubMed:28754537). Plays an important role in homeostasis of aromatic amino acids (By similarity)
- Specific Function
- amino acid transmembrane transporter activity
- Gene Name
- SLC16A10
- Uniprot ID
- Q8TF71
- Uniprot Name
- Monocarboxylate transporter 10
- Molecular Weight
- 55492.07 Da
References
- Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52