Identification
NameD-Alanine
Accession NumberDB01786  (EXPT01109)
TypeSmall Molecule
GroupsExperimental
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
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIIE3UDS4613U
CAS number338-69-2
WeightAverage: 89.0932
Monoisotopic: 89.047678473
Chemical FormulaC3H7NO2
InChI KeyQNAYBMKLOCPYGJ-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
ThermolysinProteinunknownNot AvailableGeobacillus stearothermophilusP43133 details
D-alanyl-D-alanine carboxypeptidaseProteinunknownNot AvailableStreptomyces sp. (strain R61)P15555 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-597f42bcde0e9f005b7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-ffef20b2a24280b6fac1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0007-9000000000-5494d4107e065019362aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-536fa384ea61b8df326eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-447340852e905814000eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-320cdf459ab1249aeeadView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-e42a8e9c2a1c69fb6bb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-2c2b7ae491c5edb0c9caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-4832fe79b009c4a4841eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-b70e34a4340b1eba96fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-9000000000-4f17ee45605aa5062be3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-000i-9000000000-89574d659c7bde46108eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-a2eab41650cb9ab9ccd1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-a667a47345081b445cc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-9000000000-c8d3eb600d349a1f1165View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00dl-9000000000-d03c488715b845eeccb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlanine and derivatives
Alternative ParentsD-alpha-amino acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
SubstituentsAlanine 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 FrameworkAliphatic acyclic compounds
External DescriptorsD-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
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. 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).
Gene Name:
Not Available
Uniprot ID:
P15555
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
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 July 18, 2017 17:02