Human Metabolome Database: Showing metabocard for D-Alanine (HMDB0001310)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2020-03-25 20:09:52 UTC

HMDB ID

HMDB0001310

Secondary Accession Numbers

HMDB01310

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, MeSH
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 )

Ontology

Disposition

Biological location:

Biofluid and excreta:

Source:

Endogenous

Biological:

Microbe:

Gram-positive bacteria

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	292 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	165 mg/mL	Not Available
LogP	-2.912	Not Available

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

Spectra

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

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	444.61(116.67) uM	Adult (>18 years old)	Both	Normal	26010610	details
Blood	Detected and Quantified	448.89(115.71) uM	Adult (>18 years old)	Both	Normal	26010610	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	25985090	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	18085514	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	4.98-92.078 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	5.77-78.73 umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	6.33-58.60 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	10.52-340.09 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	11.42-169.68 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details
Urine	Detected and Quantified	7.24-146.94 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	Mayo Clinic	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	247.2 (89.1) uM	Adult (>18 years old)	Female	Down syndrome pregnancy	23313728	details
Blood	Detected and Quantified	231.9 (87.3) uM	Adult (>18 years old)	Female	Pregnancy	23313728	details
Blood	Detected and Quantified	293.4 +/- 83.44 uM	Adult (>18 years old)	Female	Pregnancy with fetuses with trisomy 18	23535240	details
Blood	Detected and Quantified	258.62 +/- 85.38 uM	Adult (>18 years old)	Female	Pregnancy	23535240	details
Blood	Detected and Quantified	263.8 (51.5) uM	Adult (>18 years old)	Female	Early preeclampsia	22494326	details
Blood	Detected and Quantified	332.1 (184.2) uM	Adult (>18 years old)	Female	Pregnancy	22494326	details
Blood	Detected and Quantified	284.62 (65.96) uM	Adult (>18 years old)	Female	Pregnancy with fetus having congenital heart defect	24704061	details
Blood	Detected and Quantified	267.32 (53.39) uM	Adult (>18 years old)	Female	Pregnancy	24704061	details
Blood	Detected and Quantified	496.62(101.29) uM	Adult (>18 years old)	Both	Heart failure with preserved ejection fraction	26010610	details
Blood	Detected and Quantified	366.8 (204.8) uM	Adult (>18 years old)	Female	Late-onset preeclampsia	23159745	details
Blood	Detected and Quantified	323.8 (151.2) uM	Adult (>18 years old)	Female	Pregnancy	23159745	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	78 uM	Not Specified	Not Specified	propionic acidemia	19809936	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Early preeclampsia
Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
Pregnancy
Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ] Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ] Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ] Bahado-Singh RO, Akolekar R, Chelliah A, Mandal R, Dong E, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester trisomy 18 detection. Am J Obstet Gynecol. 2013 Jul;209(1):65.e1-9. doi: 10.1016/j.ajog.2013.03.028. Epub 2013 Mar 25. [PubMed:23535240 ] Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
Late-onset preeclampsia
Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
Propionic acidemia
Scholl-Burgi S, Haberlandt E, Gotwald T, Albrecht U, Baumgartner Sigl S, Rauchenzauner M, Rostasy K, Karall D: Stroke-like episodes in propionic acidemia caused by central focal metabolic decompensation. Neuropediatrics. 2009 Apr;40(2):76-81. doi: 10.1055/s-0029-1231065. Epub 2009 Oct 6. [PubMed:19809936 ]

Associated OMIM IDs

606054 (Propionic acidemia)

External Links

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

VMH ID

ALA_D

MarkerDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:16141519 ]
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. [PubMed:1450921 ]
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. [PubMed:8535409 ]
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. [PubMed:1426150 ]
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. [PubMed:1933416 ]
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 ]

Enzymes

Enzyme Details

1. D-amino-acid oxidase

General function:: Involved in D-amino-acid oxidase activity
Specific function:: Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:: DAO
Uniprot ID:: P14920
Molecular weight:: 39473.75

Showing metabocard for D-Alanine (HMDB0001310)

Structure for HMDB0001310 (D-Alanine)

Enzymes