Hmdb loader

Showing metabocard for D-Alanine (HMDB0001310)

Jump To Section:
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 Date2022-03-07 02:49:09 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
MOL3D 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)

HMDB0001310
     RDKit          3D
D-Alanine
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.3913   -0.4503    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1325    0.1182   -0.4052 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2810    1.3023    0.2796 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572   -0.8673   -0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8349   -1.9989   -0.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -0.5930    0.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0824   -0.8806    1.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7757   -1.2499   -0.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1295    0.3646    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084    0.3391   -1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001    1.8813    0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751    1.8379   -0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2112    0.1966    0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  6
  3 11  1  0
  3 12  1  0
  6 13  1  0
M  END
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)

HMDB0001310
     RDKit          3D
D-Alanine
 13 12  0  0  0  0  0  0  0  0999 V2000
   -1.3913   -0.4503    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1325    0.1182   -0.4052 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2810    1.3023    0.2796 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572   -0.8673   -0.3843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8349   -1.9989   -0.9263 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1604   -0.5930    0.2307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0824   -0.8806    1.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7757   -1.2499   -0.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1295    0.3646    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4084    0.3391   -1.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001    1.8813    0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9751    1.8379   -0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2112    0.1966    0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  6
  3 11  1  0
  3 12  1  0
  6 13  1  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    HMDB0001310
HETATM    1  C1  UNL     1      -1.391  -0.450   0.239  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.132   0.118  -0.405  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.281   1.302   0.280  1.00  0.00           N  
HETATM    4  C3  UNL     1       0.957  -0.867  -0.384  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.835  -1.999  -0.926  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.160  -0.593   0.231  1.00  0.00           O  
HETATM    7  H1  UNL     1      -1.082  -0.881   1.230  1.00  0.00           H  
HETATM    8  H2  UNL     1      -1.776  -1.250  -0.428  1.00  0.00           H  
HETATM    9  H3  UNL     1      -2.129   0.365   0.359  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.408   0.339  -1.459  1.00  0.00           H  
HETATM   11  H5  UNL     1      -0.500   1.881   0.651  1.00  0.00           H  
HETATM   12  H6  UNL     1       0.975   1.838  -0.276  1.00  0.00           H  
HETATM   13  H7  UNL     1       2.211   0.197   0.890  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    4   10
CONECT    3   11   12
CONECT    4    5    5    6
CONECT    6   13
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 NMR AssignmentsView 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
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
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
Experimental Chromatographic PropertiesNot 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 Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+117.71731661259
DarkChem[M-H]-111.79131661259
AllCCS[M+H]+125.58932859911
AllCCS[M-H]-123.35632859911
DeepCCS[M+H]+118.02630932474
DeepCCS[M-H]-115.22630932474
DeepCCS[M-2H]-151.72430932474
DeepCCS[M+Na]+126.46230932474
AllCCS[M+H]+125.632859911
AllCCS[M+H-H2O]+121.232859911
AllCCS[M+NH4]+129.732859911
AllCCS[M+Na]+130.932859911
AllCCS[M-H]-123.432859911
AllCCS[M+Na-2H]-128.032859911
AllCCS[M+HCOO]-133.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.0.54 minutes32390414
Predicted by Siyang on May 30, 20229.0421 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20227.06 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid355.1 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid520.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid359.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid60.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid249.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid87.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid282.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid238.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)751.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid584.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid38.2 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid631.0 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid214.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid316.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate635.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA457.0 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water382.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-AlanineC[C@@H](N)C(O)=O1700.3Standard polar33892256
D-AlanineC[C@@H](N)C(O)=O828.9Standard non polar33892256
D-AlanineC[C@@H](N)C(O)=O1236.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Alanine,1TMS,isomer #1C[C@@H](N)C(=O)O[Si](C)(C)C944.7Semi standard non polar33892256
D-Alanine,1TMS,isomer #2C[C@@H](N[Si](C)(C)C)C(=O)O1060.9Semi standard non polar33892256
D-Alanine,2TMS,isomer #1C[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1113.0Semi standard non polar33892256
D-Alanine,2TMS,isomer #1C[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1131.0Standard non polar33892256
D-Alanine,2TMS,isomer #1C[C@@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C1207.7Standard polar33892256
D-Alanine,2TMS,isomer #2C[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1279.4Semi standard non polar33892256
D-Alanine,2TMS,isomer #2C[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1153.1Standard non polar33892256
D-Alanine,2TMS,isomer #2C[C@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1457.3Standard polar33892256
D-Alanine,3TMS,isomer #1C[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1355.2Semi standard non polar33892256
D-Alanine,3TMS,isomer #1C[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1248.4Standard non polar33892256
D-Alanine,3TMS,isomer #1C[C@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1252.6Standard polar33892256
D-Alanine,1TBDMS,isomer #1C[C@@H](N)C(=O)O[Si](C)(C)C(C)(C)C1167.5Semi standard non polar33892256
D-Alanine,1TBDMS,isomer #2C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O1337.0Semi standard non polar33892256
D-Alanine,2TBDMS,isomer #1C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1537.9Semi standard non polar33892256
D-Alanine,2TBDMS,isomer #1C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1560.8Standard non polar33892256
D-Alanine,2TBDMS,isomer #1C[C@@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1523.9Standard polar33892256
D-Alanine,2TBDMS,isomer #2C[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1722.2Semi standard non polar33892256
D-Alanine,2TBDMS,isomer #2C[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1624.1Standard non polar33892256
D-Alanine,2TBDMS,isomer #2C[C@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1643.6Standard polar33892256
D-Alanine,3TBDMS,isomer #1C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1969.8Semi standard non polar33892256
D-Alanine,3TBDMS,isomer #1C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1945.9Standard non polar33892256
D-Alanine,3TBDMS,isomer #1C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1673.1Standard polar33892256
Spectra
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)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 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
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
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 Quantified366.8 (204.8) uMAdult (>18 years old)FemaleLate-onset preeclampsia details
BloodDetected and Quantified323.8 (151.2) uMAdult (>18 years old)FemalePregnancy details
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 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
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
Good Scents 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