MiMeDB: Showing metabocard for D-Alanine (MMDBc0000185)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:38:59 UTC

Update Date

2024-10-13 07:52:12 UTC

Metabolite ID

MMDBc0000185

Metabolite Identification

Common Name

D-Alanine

Description

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. http://www.dcnutrition.com/AminoAcids/). 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

Molecular Formula

C₃H₇NO₂

Average Mass

89.0932

Monoisotopic Mass

89.047678473

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

338-69-2

SMILES

Not Available

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

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

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
MMDBp0191877	D-amino-acid oxidase	Unknown	P14920	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000618	D-Alanine	Hydrogen peroxide	D-amino-acid oxidase	VMH; KEGG	9153402
MMDBr0000621	D-Alanine	D-Alanine	Not Available	VMH	30371894
MMDBr0007253	D-Alanine	D-Alanyl-D-alanine	Not Available	VMH	30371894
MMDBr0007258	L-Alanine	D-Alanine	Not Available	VMH; KEGG	30371894
MMDBr0008280	Oxoglutaric acid	D-Glutamate	Not Available	VMH	30371894
MMDBr0010808	D-Alanine	D-Alanyl-D-alanine	Not Available	VMH; KEGG	30371894
MMDBr0011014	D-Alanyl-D-alanine	D-Alanine	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Propionic acidemia		Association	Human Cerebrospinal Fluid (CSF)	HMDB	19809936

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota	Apicomplexa	1		Microbial culture
Eukaryota	Apicomplexa	1		Microbial culture
Eukaryota	Euglenozoa	1		Microbial culture
Bacteria	Firmicutes	680	Human feces; Goat feces; Sheep feces; Human ; Human vaginal secretion; Human pleural fluid plaque; Pig ; Human sputum; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	594	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Rat ; Turkey ; Sheep ; Lion ; Chicken ; American dog tick ; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria	Bacteroidetes	137	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Microbial culture; Metabolic reconstruction
Eukaryota	Euglenozoa	1		Microbial culture
Bacteria	Synergistetes	5	Human feces	Microbial culture; Metabolic reconstruction
Bacteria	Actinobacteria	199	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	18	Human feces; Human ; Relapsing fever tick	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	24	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	6		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	2		Metabolic reconstruction
Bacteria	Cyanobacteria	32	Human
Bacteria	Aquificae	2
Bacteria	Chlorobi	11
Bacteria	Deinococcus-thermus	5
Bacteria	Thermotogae	8
Bacteria	Chloroflexi	1
Bacteria	Acidobacteria	1
Bacteria	nah	2
Bacteria	Nitrospirae	1
Bacteria	Chlamydiae	4	Human
Archaea/Archaea	Euryarchaeota	2		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	3	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Food			FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	18085514
Human Cerebrospinal fluid (csf)	Detected and Quantified	78				uM	Not Specified	Not Specified	propionic acidemia	HMDB	19809936
Human Blood	Detected and Quantified	263.8 (51.5)				uM	Adult (>18 years old)	Female	Early preeclampsia	HMDB	22494326
Human Blood	Detected and Quantified	332.1 (184.2)				uM	Adult (>18 years old)	Female	Pregnancy	HMDB	22494326
Human Blood	Detected and Quantified	366.8 (204.8)				uM	Adult (>18 years old)	Female	Late-onset preeclampsia	HMDB	23159745
Human Blood	Detected and Quantified	323.8 (151.2)				uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23159745
Human Blood	Detected and Quantified	247.2 (89.1)				uM	Adult (>18 years old)	Female	Down syndrome pregnancy	HMDB	23313728
Human Blood	Detected and Quantified	231.9 (87.3)				uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23313728
Human Blood	Detected and Quantified	258.62	85.38			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23535240
Human Blood	Detected and Quantified	293.4	83.44			uM	Adult (>18 years old)	Female	Pregnancy with fetuses with trisomy 18	HMDB	23535240
Human Blood	Detected and Quantified	284.62 (65.96)				uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	HMDB	24704061
Human Blood	Detected and Quantified	267.32 (53.39)				uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	25985090
Human Blood	Detected and Quantified	496.62(101.29)				uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	HMDB	26010610
Human Blood	Detected and Quantified	444.61(116.67)				uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Blood	Detected and Quantified	448.89(115.71)				uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Bladder cancer	HMDB	28157703
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected and Quantified			10.52	340.09	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			11.42	169.68	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			7.24	146.94	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			4.98	92.078	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			5.77	78.73	umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			6.33	58.6	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Blood	Detected and Quantified	263.8	51.5			uM	Adult (>18 years old)	Female	Early preeclampsia	HMDB	22494326
Human Blood	Detected and Quantified	366.8	204.8			uM	Adult (>18 years old)	Female	Late-onset preeclampsia	HMDB	23159745
Human Blood	Detected and Quantified	231.9	87.3			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23313728
Human Blood	Detected and Quantified	258.62	85.38			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23535240
Human Blood	Detected and Quantified	267.32	53.39			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	24704061
Human Blood	Detected and Quantified	323.8	151.2			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	23159745
Human Blood	Detected and Quantified	332.1	184.2			uM	Adult (>18 years old)	Female	Pregnancy	HMDB	22494326
Human Cerebrospinal fluid (csf)	Detected and Quantified	78				uM	Not Specified	Not Specified	propionic acidemia	HMDB	19809936
Human Blood	Detected and Quantified	444.61	116.67			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Blood	Detected and Quantified	448.89	115.71			uM	Adult (>18 years old)	Both	Normal	HMDB	26010610
Human Urine	Detected and Quantified			10.52	340.09	umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			11.42	169.68	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			4.98	92.078	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			5.77	78.73	umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			6.33	58.60	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Urine	Detected and Quantified			7.24	146.94	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	Mayo Clinic (https://neurology.testcatalog.org/show/AAPD)
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	18085514
Human Feces	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	25985090
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0001310

DrugBank ID

DB01786

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

Not Available

PubChem Compound

71080

PDB ID

Not Available

ChEBI ID

15570

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Nagata Y, Masui R, Akino T: The presence of free D-serine, D-alanine and D-proline in human plasma. Experientia. 1992 Oct 15;48(10):986-8. doi: 10.1007/BF01919147. [PubMed:1426150 ]
D'Aniello A, Vetere A, Fisher GH, Cusano G, Chavez M, Petrucelli L: Presence of D-alanine in proteins of normal and Alzheimer human brain. Brain Res. 1992 Oct 2;592(1-2):44-8. doi: 10.1016/0006-8993(92)91656-y. [PubMed:1450921 ]
Fisher GH, D'Aniello A, Vetere A, Padula L, Cusano GP, Man EH: Free D-aspartate and D-alanine in normal and Alzheimer brain. Brain Res Bull. 1991 Jun;26(6):983-5. doi: 10.1016/0361-9230(91)90266-m. [PubMed:1933416 ]
Fukushima T, Santa T, Homma H, Nagatomo R, Imai K: Determination of D-amino acids in serum from patients with renal dysfunction. Biol Pharm Bull. 1995 Aug;18(8):1130-2. doi: 10.1248/bpb.18.1130. [PubMed:8535409 ]
Hamase K, Konno R, Morikawa A, Zaitsu K: Sensitive determination of D-amino acids in mammals and the effect of D-amino-acid oxidase activity on their amounts. Biol Pharm Bull. 2005 Sep;28(9):1578-84. doi: 10.1248/bpb.28.1578. [PubMed:16141519 ]
Radkov AD, Moe LA: Bacterial synthesis of D-amino acids. Appl Microbiol Biotechnol. 2014 Jun;98(12):5363-74. doi: 10.1007/s00253-014-5726-3. Epub 2014 Apr 22. [PubMed:24752840 ]

Showing metabocard for D-Alanine (MMDBc0000185)

MOL for #<Metabolite:0x00007f46c1a9d378>

3D MOL for #<Metabolite:0x00007f46c1a9d378>

3D SDF for #<Metabolite:0x00007f46c1a9d378>

3D-SDF for #<Metabolite:0x00007f46c1a9d378>

PDB for #<Metabolite:0x00007f46c1a9d378>

3D PDB for #<Metabolite:0x00007f46c1a9d378>

SMILES for #<Metabolite:0x00007f46c1a9d378>

INCHI for #<Metabolite:0x00007f46c1a9d378>

Structure for #<Metabolite:0x00007f46c1a9d378>

3D Structure for #<Metabolite:0x00007f46c1a9d378>