ChemFOnt: Showing chemical card for D-Alanine (CFc000001009)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:33 UTC

Chemfont ID

CFc000001009

Molecule Identification

Common Name

D-Alanine

Definition

Alanine is a nonessential amino acid made in the body from the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (Branched Chain Amino Acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as regulator in glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine and glycine, is an inhibitory neurotransmitter in the brain. Alanine can be found in some Gram-positive bacteria (PMID:24752840 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2-Aminopropanoic acid	ChEBI
(R)-2-Aminopropanoic acid	ChEBI
(R)-Alanine	ChEBI
D-2-Aminopropionic acid	ChEBI
D-Ala	ChEBI
D-Alanin	ChEBI
D-alpha-Alanine	ChEBI
D-alpha-Aminopropionic acid	ChEBI
DAL	ChEBI
(2R)-2-Aminopropanoate	Generator
(R)-2-Aminopropanoate	Generator
D-2-Aminopropionate	Generator
D-a-Alanine	Generator
D-Α-alanine	Generator
D-a-Aminopropionate	Generator
D-a-Aminopropionic acid	Generator
D-alpha-Aminopropionate	Generator
D-Α-aminopropionate	Generator
D-Α-aminopropionic acid	Generator
Alanine	HMDB
D(-)-a -Alanine	HMDB
D(-)-alpha-Alanine	HMDB
D-(-)-Alanine	HMDB
(2R)-2-Aminopropionic acid	HMDB
(R)-2-Aminopropionic acid	HMDB
D(-)-Α-alanine	HMDB

Chemical Formula

C₃H₇NO₂

Average Molecular Weight

89.0932

Monoisotopic Molecular Weight

89.047678473

IUPAC Name

(2R)-2-aminopropanoic acid

Traditional Name

D-alanine

CAS Registry Number

338-69-2

SMILES

C[C@@H](N)C(O)=O

InChI Identifier

InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1

InChI Key

QNAYBMKLOCPYGJ-UWTATZPHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives 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

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
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Organopnictogen compound
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:15570 )
alanine (CHEBI:15570 )
Other amino acids (C00133 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 22494326)
Cerebrospinal Fluid (CSF) (PMID: 19809936)
Cerebrospinal fluid (HMDB: HMDB0001310)

Excreta

Biofluid or Excreta

Feces (PMID: 18085514)
Urine (PMID: 28157703)

Source

Exogenous

Exogenous (HMDB: HMDB0001310)

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)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Endogenous

Endogenous (HMDB: HMDB0001310)

Microbe

Microbe (HMDB: HMDB0001310)
Gram-positive bacteria (HMDB: HMDB0001310)

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)
Inner Membrane Transport (PathBank: SMP0121270)
L-Alanine Metabolism (PathBank: SMP0121272)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001310)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	447 g/L	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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon