Showing Compound D-Alanine (FDB022546)

Record Information

Version

1.0

Creation date

2011-09-21 00:15:40 UTC

Update date

2025-11-19 02:41:56 UTC

Primary ID

FDB022546

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

D-Alanine

Description

Amino acids are one of the most important molecules in living organisms, and most of them have a chiral carbon at a -position. In the higher animals, a large part of the naturally occurring amino acids is the L-form, and the stereoisomers (D-amino acids) had been believed to be rare. However, several D-amino acids have been found in mammals including humans, and their distributions, functions and origins have gradually been clarified. The D-alanine (D-Ala) amounts have also been reported to change in the case of diseases. Proteins of the frontal lobe white and gray matter of human brains, both normal and Alzheimer subjects, contain D-alanine at concentrations between 0.50 and 1.28 mumol/g of wet tissue, 50-70-times lower than the concentration of L-alanine. D-Alanine have been detected in the sera of both normal subjects and patients with renal dysfunction, and their concentrations were higher in the patients than in the normal subjects. (PMID: 16141519, 1450921, 8535409, 1426150, 1933416) [HMDB]

CAS Number

338-69-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	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
D-Alanine	hmdb
D-α-alanine	Generator
D-α-aminopropionate	Generator
D-α-aminopropionic acid	Generator
delta-(-)-Alanine	hmdb
delta-2-Aminopropionic acid	hmdb
delta-Alanine	hmdb
delta-alpha-Alanine	hmdb

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

Chemical Formula

C3H7NO2

IUPAC name

(2R)-2-aminopropanoic acid

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

Isomeric SMILES

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

Average Molecular Weight

89.0932

Monoisotopic Molecular Weight

89.047678473

Classification

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 )

Ontology

Disposition

Biological location:

Biofluid and excreta:

Source:

Endogenous

Biological:

Microbe:

Gram-positive bacteria

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	D-Alanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-d31f7a2ed8284a740b59	Spectrum
Predicted GC-MS	D-Alanine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9500000000-d9aff70e7ddd0c94cf50	Spectrum
Predicted GC-MS	D-Alanine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9000000000-597f42bcde0e9f005b7e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-ffef20b2a24280b6fac1	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0007-9000000000-5494d4107e065019362a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-536fa384ea61b8df326e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-447340852e905814000e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0006-9000000000-320cdf459ab1249aeead	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0006-9000000000-e42a8e9c2a1c69fb6bb2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9000000000-2c2b7ae491c5edb0c9ca	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-4832fe79b009c4a4841e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9000000000-b70e34a4340b1eba96fb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-536fa384ea61b8df326e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-447340852e905814000e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-9000000000-4f17ee45605aa5062be3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-9000000000-89574d659c7bde46108e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-a2eab41650cb9ab9ccd1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-a667a47345081b445cc9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-2c2b7ae491c5edb0c9ca	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-4832fe79b009c4a4841e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-b70e34a4340b1eba96fb	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-080ffbbf05d95b7bcfe6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-0dfcc5cb0b7d9f01e04a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9000000000-130c999fe6b63419cfa1	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-2ddc0bb04bae8f928a23	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-98c403c9cd494594babf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-38a12affa4e4f4e91626	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum