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Showing metabocard for D-Alanine (HMDB0001310)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:00:08 UTC
HMDB IDHMDB0001310
Secondary Accession Numbers
  • HMDB01310
Metabolite Identification
Common NameD-Alanine
DescriptionAlanine 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. Alanine can be found in some Gram-positive bacteria (PMID:24752840 ).
Structure
Data?1582752191
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001310 (D-Alanine)


  Mrv1652302112018342D          

  6  5  0  0  0  0            999 V2000
   -0.0444    0.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7590    0.3348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444    1.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6700    0.3348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6700   -0.4901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845    0.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  6  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  4  5  1  1  0  0  0
M  END
Download

3D MOL for HMDB0001310 (D-Alanine)

Download
3D SDF for HMDB0001310 (D-Alanine)

  Mrv1652302112018342D          

  6  5  0  0  0  0            999 V2000
   -0.0444    0.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7590    0.3348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444    1.5724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6700    0.3348    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6700   -0.4901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3845    0.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  6  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  4  5  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0001310

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C3H7NO2

> <MOLECULAR_WEIGHT>
89.0932

> <EXACT_MASS>
89.047678473

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
8.541111445673307

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-aminopropanoic acid

> <ALOGPS_LOGP>
-3.05

> <JCHEM_LOGP>
-2.8407879097329416

> <ALOGPS_LOGS>
0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.474897471379417

> <JCHEM_PKA_STRONGEST_BASIC>
9.476905287351833

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
20.497300000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.47e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-alanine

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0001310 (D-Alanine)
https://cactus.nci.nih.gov/chemical/structure/C%5BC@@H%5D(N)C(O)=O/file?forma...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:12})
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.2037    1.3768   -0.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7236    0.1803    0.4050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7930    0.4188    1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650   -0.9871    0.1093 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7082   -0.1303    0.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6616    0.7958    0.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9981   -1.2130   -0.3988 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1344    1.1383   -1.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2394    1.6014   -0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5794    2.2429   -0.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2287   -1.8067    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5307   -0.8038    0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5654    0.5505   -0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  1  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  6 13  1  0  0  0  0
M  END
$$$$

Download
PDB for HMDB0001310 (D-Alanine)
HEADER    PROTEIN                                 11-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-FEB-20         0                                  
HETATM    1  C   UNK     0      -0.083   1.395   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.417   0.625   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -0.083   2.935   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.251   0.625   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.251  -0.915   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.584   1.395   0.000  0.00  0.00           C+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    6    5                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

Download
3D PDB for HMDB0001310 (D-Alanine)
COMPND    https://cactus.nci.nih.gov/chemical/structure/C%5BC@@H%5D(N)C(O)=O/file?forma... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
ATOM      1  CB  ALA A   1      -1.204   1.377  -0.419  1.00  0.00           C  
ATOM      2  CA  ALA A   1      -0.724   0.180   0.405  1.00  0.00           C  
ATOM      3  HA  ALA A   1      -0.793   0.419   1.466  1.00  0.00           H  
ATOM      4  N   ALA A   1      -1.565  -0.987   0.109  1.00  0.00           N  
ATOM      5  C   ALA A   1       0.708  -0.130   0.052  1.00  0.00           C  
ATOM      6  O   ALA A   1       1.662   0.796   0.240  1.00  0.00           O  
ATOM      7  OXT ALA A   1       0.998  -1.213  -0.399  1.00  0.00           O  
ATOM      8  HB1 ALA A   1      -1.134   1.138  -1.480  1.00  0.00           H  
ATOM      9  HB2 ALA A   1      -2.239   1.601  -0.164  1.00  0.00           H  
ATOM     10  HB3 ALA A   1      -0.579   2.243  -0.200  1.00  0.00           H  
ATOM     11  H1  ALA A   1      -1.229  -1.807   0.592  1.00  0.00           H  
ATOM     12  H2  ALA A   1      -2.531  -0.804   0.337  1.00  0.00           H  
ATOM     13  H   ALA A   1       2.565   0.550  -0.001  1.00  0.00           H  
CONECT    1    2    8    9   10                                       
CONECT    2    1    3    4    5                                       
CONECT    3    2                                                      
CONECT    4    2   11   12                                            
CONECT    5    2    6    7    7                                       
CONECT    6    5   13                                                 
CONECT    7    5    5                                                 
CONECT    8    1                                                      
CONECT    9    1                                                      
CONECT   10    1                                                      
CONECT   11    4                                                      
CONECT   12    4                                                      
CONECT   13    6                                                      
MASTER        0    0    0    0    0    0    0    0   13    0   13    0
END

Download
SMILES for HMDB0001310 (D-Alanine)
C[C@@H](N)C(O)=O
Download
INCHI for HMDB0001310 (D-Alanine)
InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
(2R)-2-Aminopropanoic acidChEBI
(R)-2-Aminopropanoic acidChEBI
(R)-AlanineChEBI
D-2-Aminopropionic acidChEBI
D-AlaChEBI
D-AlaninChEBI
D-alpha-AlanineChEBI
D-alpha-Aminopropionic acidChEBI
DALChEBI
(2R)-2-AminopropanoateGenerator
(R)-2-AminopropanoateGenerator
D-2-AminopropionateGenerator
D-a-AlanineGenerator
D-Α-alanineGenerator
D-a-AminopropionateGenerator
D-a-Aminopropionic acidGenerator
D-alpha-AminopropionateGenerator
D-Α-aminopropionateGenerator
D-Α-aminopropionic acidGenerator
AlanineHMDB
D(-)-a -AlanineHMDB
D(-)-alpha-AlanineHMDB
D-(-)-AlanineHMDB
(2R)-2-Aminopropionic acidHMDB
(R)-2-Aminopropionic acidHMDB
D(-)-Α-alanineHMDB
Chemical FormulaC3H7NO2
Average Molecular Weight89.0932
Monoisotopic Molecular Weight89.047678473
IUPAC Name(2R)-2-aminopropanoic acid
Traditional NameD-alanine
CAS Registry Number338-69-2
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 KeyQNAYBMKLOCPYGJ-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.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlanine 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition
Biological location:
Source:
Role
Industrial application:
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point292 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility165 mg/mLNot Available
LogP-2.912Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility447 g/LALOGPS
logP-3ALOGPS
logP-2.8ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.5 m³·mol⁻¹ChemAxon
Polarizability8.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties
Collision Cross Sections
NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available117.71731661259  
DarkChem[M-H]-PredictedNot Available111.79131661259  
AllCCS[M+H]+PredictedNot Available125.58932859911  
AllCCS[M-H]-PredictedNot Available123.35632859911  
Retention Indices
Underivatized
Not Available
Derivatized
DerivativeValueReference
D-Alanine,1TMS,#1944.7369https://arxiv.org/abs/1905.12712
D-Alanine,1TMS,#21060.9442https://arxiv.org/abs/1905.12712
D-Alanine,1TBDMS,#11167.5343https://arxiv.org/abs/1905.12712
D-Alanine,1TBDMS,#21337.0369https://arxiv.org/abs/1905.12712
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-d31f7a2ed8284a740b592016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9500000000-d9aff70e7ddd0c94cf502017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-bda90c19fd0d70cb909b2021-09-05View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-597f42bcde0e9f005b7e2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-ffef20b2a24280b6fac12012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0007-9000000000-5494d4107e065019362a2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-536fa384ea61b8df326e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-447340852e905814000e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-320cdf459ab1249aeead2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-e42a8e9c2a1c69fb6bb22012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-2c2b7ae491c5edb0c9ca2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-4832fe79b009c4a4841e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9000000000-b70e34a4340b1eba96fb2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-536fa384ea61b8df326e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-447340852e905814000e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  , negativesplash10-000i-9000000000-4f17ee45605aa5062be32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  , negativesplash10-000i-9000000000-89574d659c7bde46108e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-a2eab41650cb9ab9ccd12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-a667a47345081b445cc92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-2c2b7ae491c5edb0c9ca2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-4832fe79b009c4a4841e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-b70e34a4340b1eba96fb2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0006-9000000000-080ffbbf05d95b7bcfe62016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0006-9000000000-0dfcc5cb0b7d9f01e04a2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-002f-9000000000-130c999fe6b63419cfa12016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-000i-9000000000-2ddc0bb04bae8f928a232016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-000i-9000000000-98c403c9cd494594babf2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-00di-9000000000-38a12affa4e4f4e916262016-09-12View Spectrum
NMR
Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)2016-10-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
    • 

  • Cerebrospinal Fluid (CSF)
    • 

  • Feces
    • 

  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified444.61(116.67) uMAdult (>18 years old)BothNormal  details
BloodDetected and Quantified448.89(115.71) uMAdult (>18 years old)BothNormal  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
 
Normal		  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
UrineDetected and Quantified4.98-92.078 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal  details
UrineDetected and Quantified5.77-78.73 umol/mmol creatinineAdolescent (13-18 years old)Not SpecifiedNormal  details
UrineDetected and Quantified6.33-58.60 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal  details
UrineDetected and Quantified10.52-340.09 umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal  details
UrineDetected and Quantified11.42-169.68 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal  details
UrineDetected and Quantified7.24-146.94 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal  details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified247.2 (89.1)  uMAdult (>18 years old)FemaleDown syndrome pregnancy  details
BloodDetected and Quantified231.9 (87.3)  uMAdult (>18 years old)FemalePregnancy  details
BloodDetected and Quantified293.4 +/- 83.44  uMAdult (>18 years old)Female
 
Pregnancy with fetuses with trisomy 18		  details
BloodDetected and Quantified258.62 +/- 85.38  uMAdult (>18 years old)FemalePregnancy  details
BloodDetected and Quantified263.8 (51.5)  uMAdult (>18 years old)FemaleEarly preeclampsia  details
BloodDetected and Quantified332.1 (184.2)  uMAdult (>18 years old)FemalePregnancy  details
BloodDetected and Quantified284.62 (65.96)  uMAdult (>18 years old)FemalePregnancy with fetus having congenital heart defect  details
BloodDetected and Quantified267.32 (53.39)  uMAdult (>18 years old)FemalePregnancy  details
BloodDetected and Quantified496.62(101.29) uMAdult (>18 years old)BothHeart failure with preserved ejection fraction  details
BloodDetected and Quantified366.8 (204.8) uMAdult (>18 years old)FemaleLate-onset preeclampsia  details
BloodDetected and Quantified323.8 (151.2)  uMAdult (>18 years old)FemalePregnancy  details
Cerebrospinal Fluid (CSF)Detected and Quantified78 uMNot SpecifiedNot Specifiedpropionic acidemia  details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer  details
Associated Disorders and Diseases
Disease References
Early preeclampsia
  1. 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
  1. 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  ] 
  2. 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  ] 
  3. 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  ] 
  4. 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  ] 
  5. 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
  1. 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
  1. 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
DrugBank IDDB01786  
Phenol Explorer Compound IDNot Available
FooDB IDFDB022546  
KNApSAcK IDC00019654  
Chemspider ID64234  
KEGG Compound IDC00133  
BioCyc IDD-ALANINE  
BiGG ID33977  
Wikipedia LinkAlanine  
METLIN IDNot Available
PubChem Compound71080  
PDB IDNot Available
ChEBI ID15570  
Food Biomarker OntologyNot Available
VMH IDALA_D  
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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  ] 
  2. 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  ] 
  3. 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  ] 
  4. 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  ] 
  5. 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  ] 
  6. 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