MiMeDB: Showing metabocard for N-Acetyl-D-alanine (MMDBc0033162)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:37:13 UTC

Update Date

2025-10-07 16:07:56 UTC

Metabolite ID

MMDBc0033162

Metabolite Identification

Common Name

N-Acetyl-D-alanine

Description

N-Acetyl-D-alanine is a member of the amino acid derivatives chemical class, specifically categorized as an N-acetylated amino acid. Its chemical structure features an acetyl group attached to the nitrogen of the D-alanine molecule, influencing its biochemical properties and interactions. N-Acetyl-D-alanine is involved in various biochemical pathways, including its role as a substrate for D-amino acid oxidase (DAAO), where it has been shown to increase reactive oxygen species (ROS) production in transfected HeLa cells (PMID:17508907 ). Additionally, it serves as a competing agent in displacement studies on vancomycin-based stationary phases, highlighting its relevance in chromatographic applications (PMID:11881709 ). The binding characteristics of N-acetyl-D-alanine have been investigated in relation to D,L-dansyl amino acids, further emphasizing its utility in analytical chemistry (PMID:11881709 ). Furthermore, the crystal structure of vancomycin in complex with N-acetyl-D-alanine has been elucidated, providing insights into its molecular interactions (PMID:9578636 ). Overall, N-acetyl-D-alanine's unique structural features and its involvement in various biochemical processes underscore its significance in both chemistry and biology.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-acetylamino-Propionic acid	ChEMBL
Acetyl-D-alanine	ChEMBL
2-acetylamino-Propionate	Generator
N-Acetyl-L-alanine	MeSH
N-Acetylalanine	MeSH

Molecular Formula

C₅H₉NO₃

Average Mass

131.1299

Monoisotopic Mass

131.058243159

IUPAC Name

(2R)-2-acetamidopropanoic acid

Traditional Name

N-acetylalanine

CAS Registry Number

97-69-8

SMILES

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

InChI Identifier

InChI=1S/C5H9NO3/c1-3(5(8)9)6-4(2)7/h3H,1-2H3,(H,6,7)(H,8,9)/t3-/m1/s1

InChI Key

KTHDTJVBEPMMGL-GSVOUGTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Alanine or derivatives
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	43.6 g/L	ALOGPS
logP	-0.53	ALOGPS
logP	-0.76	ChemAxon
logS	-0.48	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	29.94 m³·mol⁻¹	ChemAxon
Polarizability	12.53 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-82510327b6f9313f2dec	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0019-9600000000-98787fdcdf179af3efc6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000f-9000000000-c9b855453cf3c68830bf	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-4178e09fa261bbb5e7e9	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-4900000000-2739a6e8536aca9442cc	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9200000000-2df5117d1f0498fa4d47	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0076-9000000000-74175a91d6530fa275df	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	316.0
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	180.6
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	142.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	299.0
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	252.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	336.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	995.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	265.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	832.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	203.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	277.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	193.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	63.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	270.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	646.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	58.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	200.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	824.9
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	629.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	N-Acetyl-D-alanine_TMS_1	CC(=O)N[C@H](C)C(=O)O[Si](C)(C)C	standard non polar	2025-10-24	1672.68
Gas Chromatography	N-Acetyl-D-alanine_TMS_2	CC(=O)N([C@H](C)C(=O)O)[Si](C)(C)C	standard non polar	2025-10-24	1990.09
Gas Chromatography	N-Acetyl-D-alanine_TMS_3	CC(=O)N([C@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-24	2159.49
Gas Chromatography	N-Acetyl-D-alanine_TMS_1	CC(=O)N[C@H](C)C(=O)O[Si](C)(C)C	standard polar	2025-10-24	2061.36
Gas Chromatography	N-Acetyl-D-alanine_TMS_2	CC(=O)N([C@H](C)C(=O)O)[Si](C)(C)C	standard polar	2025-10-24	2117.49
Gas Chromatography	N-Acetyl-D-alanine_TMS_3	CC(=O)N([C@H](C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-24	2193.47

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0026115	Acetyl-CoA	N-Acetyl-D-alanine	D-amino-acid N-acetyltransferase HPA3	Acetylation	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132213

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Yow GY, Uo T, Yoshimura T, Esaki N: D-amino acid N-acetyltransferase of Saccharomyces cerevisiae: a close homologue of histone acetyltransferase Hpa2p acting exclusively on free D-amino acids. Arch Microbiol. 2004 Nov;182(5):396-403. doi: 10.1007/s00203-004-0724-y. [PubMed:15375647 ]
Yow GY, Uo T, Yoshimura T, Esaki N: Physiological role of D-amino acid-N-acetyltransferase of Saccharomyces cerevisiae: detoxification of D-amino acids. Arch Microbiol. 2006 Mar;185(1):39-46. doi: 10.1007/s00203-005-0060-x. Epub 2005 Dec 14. [PubMed:16362288 ]
Scheer M, Grote A, Chang A, Schomburg I, Munaretto C, Rother M, Sohngen C, Stelzer M, Thiele J, Schomburg D: BRENDA, the enzyme information system in 2011. Nucleic Acids Res. 2011 Jan;39(Database issue):D670-6. doi: 10.1093/nar/gkq1089. Epub 2010 Nov 9. [PubMed:21062828 ]

Showing metabocard for N-Acetyl-D-alanine (MMDBc0033162)

MOL for #<Metabolite:0x00007f9af11bb6e0>

3D MOL for #<Metabolite:0x00007f9af11bb6e0>

3D SDF for #<Metabolite:0x00007f9af11bb6e0>

3D-SDF for #<Metabolite:0x00007f9af11bb6e0>

PDB for #<Metabolite:0x00007f9af11bb6e0>

3D PDB for #<Metabolite:0x00007f9af11bb6e0>

SMILES for #<Metabolite:0x00007f9af11bb6e0>

INCHI for #<Metabolite:0x00007f9af11bb6e0>

Structure for #<Metabolite:0x00007f9af11bb6e0>

3D Structure for #<Metabolite:0x00007f9af11bb6e0>