Identification

Name
D-Alanine
Accession Number
DB01786  (EXPT01109)
Type
Small Molecule
Groups
Experimental
Description

The D-enantiomer of alanine.

Structure
Thumb
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
Categories
Not Available
UNII
E3UDS4613U
CAS number
338-69-2
Weight
Average: 89.0932
Monoisotopic: 89.047678473
Chemical Formula
C3H7NO2
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThermolysinNot AvailableGeobacillus stearothermophilus
UD-alanyl-D-alanine carboxypeptidaseNot AvailableStreptomyces 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
IUPHAR
720
Guide to Pharmacology
GtP Drug Page
HET
DAL
PDB Entries
148l / 1aj1 / 1bck / 1bfw / 1bzv / 1c0p / 1c4b / 1c5f / 1csa / 1cwa
show 250 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)292 °CPhysProp
water solubility1.65E+005 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
Predicted Properties
PropertyValueSource
Water Solubility447.0 mg/mLALOGPS
logP-3ALOGPS
logP-2.8ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.5 m3·mol-1ChemAxon
Polarizability8.54 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9506
Blood Brain Barrier+0.6314
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.8222
P-glycoprotein inhibitor INon-inhibitor0.9919
P-glycoprotein inhibitor IINon-inhibitor0.9952
Renal organic cation transporterNon-inhibitor0.9644
CYP450 2C9 substrateNon-substrate0.8125
CYP450 2D6 substrateNon-substrate0.8851
CYP450 3A4 substrateNon-substrate0.8204
CYP450 1A2 substrateNon-inhibitor0.946
CYP450 2C9 inhibitorNon-inhibitor0.9645
CYP450 2D6 inhibitorNon-inhibitor0.9748
CYP450 2C19 inhibitorNon-inhibitor0.9797
CYP450 3A4 inhibitorNon-inhibitor0.9384
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9938
Ames testNon AMES toxic0.9339
CarcinogenicityNon-carcinogens0.62
BiodegradationReady biodegradable0.7662
Rat acute toxicity1.0339 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9891
hERG inhibition (predictor II)Non-inhibitor0.9841
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-597f42bcde0e9f005b7e
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0006-9000000000-ffef20b2a24280b6fac1
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0007-9000000000-5494d4107e065019362a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-000i-9000000000-536fa384ea61b8df326e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-000i-9000000000-447340852e905814000e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0006-9000000000-320cdf459ab1249aeead
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0006-9000000000-e42a8e9c2a1c69fb6bb2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0006-9000000000-2c2b7ae491c5edb0c9ca
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0006-9000000000-4832fe79b009c4a4841e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0006-9000000000-b70e34a4340b1eba96fb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-536fa384ea61b8df326e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-000i-9000000000-447340852e905814000e
MS/MS Spectrum - , negativeLC-MS/MSsplash10-000i-9000000000-4f17ee45605aa5062be3
MS/MS Spectrum - , negativeLC-MS/MSsplash10-000i-9000000000-89574d659c7bde46108e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-a2eab41650cb9ab9ccd1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-a667a47345081b445cc9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-2c2b7ae491c5edb0c9ca
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-4832fe79b009c4a4841e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9000000000-b70e34a4340b1eba96fb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-9000000000-c8d3eb600d349a1f1165
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dl-9000000000-d03c488715b845eeccb0
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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 / Alpha-amino acid / D-alpha-amino acid / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Hydrocarbon derivative / Organic oxygen compound / Primary amine / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
D-alpha-amino acid, alanine (CHEBI:15570) / Other amino acids (C00133)

Targets

Kind
Protein
Organism
Geobacillus stearothermophilus
Pharmacological action
Unknown
General Function
Metalloendopeptidase activity
Specific Function
Extracellular zinc metalloprotease.
Gene Name
nprS
Uniprot ID
P43133
Uniprot Name
Thermolysin
Molecular Weight
60616.22 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Streptomyces sp. (strain R61)
Pharmacological action
Unknown
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific 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....
Gene Name
Not Available
Uniprot ID
P15555
Uniprot Name
D-alanyl-D-alanine carboxypeptidase
Molecular Weight
42916.725 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity).
Gene Name
SLC16A10
Uniprot ID
Q8TF71
Uniprot Name
Monocarboxylate transporter 10
Molecular Weight
55492.07 Da
References
  1. 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. [PubMed:11278508]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 13:09