D-Alanine (YMDB00993)

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Identification

YMDB ID

YMDB00993

Name

D-Alanine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

D-Alanine, also known as D-ala or (R)-alanine, 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. D-Alanine is a very strong basic compound (based on its pKa). D-Alanine exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(2R)-2-aminopropanoic acid
(R)-2-aminopropanoic acid
(R)-Alanine
Alanine
Alanine, D-
D-(-)-Alanine
d-2-aminopropionic acid
D-Ala
D-Alanin
D-Alanine
D-alpha-Alanine
D-alpha-aminopropionic acid
D(-)-a -Alanine
D(-)-alpha-Alanine
delta-(-)-Alanine
delta-2-Aminopropionic acid
delta-Alanine
delta-alpha-Alanine
dl-Alanine
DAL
(2R)-2-Aminopropanoate
(R)-2-Aminopropanoate
D-2-Aminopropionate
D-a-Alanine
D-Α-alanine
D-a-Aminopropionate
D-a-Aminopropionic acid
D-alpha-Aminopropionate
D-Α-aminopropionate
D-Α-aminopropionic acid
(2R)-2-Aminopropionic acid
(R)-2-Aminopropionic acid
D(-)-Α-alanine

CAS number

338-69-2

Weight

Average: 89.0932
Monoisotopic: 89.047678473

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

Traditional IUPAC Name

D-alanine

Chemical Formula

C₃H₇NO₂

SMILES

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

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 )

Physical Properties

State

Solid

Charge

Melting point

300 °C

Experimental Properties

Property	Value	Reference
Water Solubility	164 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	-2.85 [SANGSTER (1994)]	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Vitamin B6 metabolism

ec00750

SMPDB Reactions

L-Alanine ↔ D-Alanine

D-Alanine + Adenosine triphosphate → D-Alanyl-D-alanine + ADP + phosphate

D-Alanine + water + Quinone → Ammonium + Pyruvic acid + Hydroquinone

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-d31f7a2ed8284a740b59	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9500000000-d9aff70e7ddd0c94cf50	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9000000000-597f42bcde0e9f005b7e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-ffef20b2a24280b6fac1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0007-9000000000-5494d4107e065019362a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-536fa384ea61b8df326e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-447340852e905814000e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0006-9000000000-320cdf459ab1249aeead	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0006-9000000000-e42a8e9c2a1c69fb6bb2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0006-9000000000-2c2b7ae491c5edb0c9ca	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-4832fe79b009c4a4841e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9000000000-b70e34a4340b1eba96fb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-536fa384ea61b8df326e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-447340852e905814000e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-9000000000-4f17ee45605aa5062be3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-9000000000-89574d659c7bde46108e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-a2eab41650cb9ab9ccd1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-a667a47345081b445cc9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-2c2b7ae491c5edb0c9ca	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-4832fe79b009c4a4841e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-b70e34a4340b1eba96fb	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-080ffbbf05d95b7bcfe6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-0dfcc5cb0b7d9f01e04a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9000000000-130c999fe6b63419cfa1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-2ddc0bb04bae8f928a23	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-98c403c9cd494594babf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-38a12affa4e4f4e91626	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Yow, G. Y., Uo, T., Yoshimura, T., Esaki, N. (2004). "D-amino acid N-acetyltransferase of Saccharomyces cerevisiae: a close homologue of histone acetyltransferase Hpa2p acting exclusively on free D-amino acids." Arch Microbiol 182:396-403.15375647

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	15570
HMDB ID	HMDB01310
Pubchem Compound ID	71080
Kegg ID	C00133
ChemSpider ID	64234
FOODB ID	FDB022546
Wikipedia	Alanine
BioCyc ID	D-ALANINE

Enzymes

Protein Details

1. N-acetyltransferase HPA3

General function:: Involved in N-acetyltransferase activity
Specific function:: N-acetyltransferase whose physiological acetyl acceptor substrate is still unknown. In vitro, histone acetylation is very weak
Gene Name:: HPA3
Uniprot ID:: P39979
Molecular weight:: 20698.5

Reactions

acetyl-CoA + a D-amino acid → CoA + an N-acetyl-D-amino acid

Structure for #<Compound:0x0543ef04>

Enzymes

Reactions