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Showing NP-Card for D-Alanine (NP0000640)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:17 UTC
NP-MRD IDNP0000640
Secondary Accession NumbersNone
Natural Product 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000640 (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 NP0000640 (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 NP0000640 (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>
NP0000640

> <DATABASE_NAME>
NP-MRD

> <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 NP0000640 (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 NP0000640 (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
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3D PDB for NP0000640 (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
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SMILES for NP0000640 (D-Alanine)

C[C@@H](N)C(O)=O
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INCHI for NP0000640 (D-Alanine)

InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1
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View in JSmol
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 Mass89.0932 Da
Monoisotopic Mass89.04768 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea millefoliumLOTUS Database
Allium sativumLOTUS Database
Amaranthus spinosusLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Artemia salinaLOTUS Database
Artemisia absinthiumLOTUS Database
Astragalus hamosusLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica napusLOTUS Database
Bubalus bubalisFooDB
Byrsonima crassifoliaLOTUS Database
Calendula officinalisLOTUS Database
Cannabis sativaLOTUS Database
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Cucurbita foetidissimaLOTUS Database
Cycas circinalisLOTUS Database
Daucus carotaLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Euphorbia prostrataLOTUS Database
Flammulina velutipesLOTUS Database
Fragaria x ananassaLOTUS Database
Gallus gallusFooDB
Ginkgo bilobaLOTUS Database
Glycine maxLOTUS Database
Homo sapiensLOTUS Database
Indigofera hirsutaLOTUS Database
Iochroma fuchsioidesLOTUS Database
Jatropha gossypifoliaLOTUS Database
Lagopus mutaFooDB
Lathyrus sativusLOTUS Database
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Morchella angusticepsLOTUS Database
Neptunea antiquaLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
Opuntia ficus-indicaLOTUS Database
OryctolagusFooDB
Ovis ariesFooDB
Panax ginsengLOTUS Database
Parastichopus regalisLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Picea pungensLOTUS Database
Pinus densifloraLOTUS Database
Pinus ponderosaLOTUS Database
Pisum sativumLOTUS Database
Pleurotus ostreatusLOTUS Database
Prunus domesticaLOTUS Database
Psophocarpus tetragonolobusLOTUS Database
Ramalina fraxineaLOTUS Database
Ripariosida hermaphroditaLOTUS Database
Sagittaria sagittifoliaLOTUS Database
Sargassum fulvellumLOTUS Database
Senna obtusifoliaLOTUS Database
Spermacoce pusillaLOTUS Database
Stangeria eriopusLOTUS Database
Struthio camelusFooDB
Styphnolobium japonicumLOTUS Database
Suaeda aegyptiacaLOTUS Database
Suaeda nudifloraLOTUS Database
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Telekia speciosaLOTUS Database
Thymus transcaucasicusLOTUS Database
Treculia africanaLOTUS Database
Valeriana officinalisLOTUS Database
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point292 °CNot Available
Boiling Point212.91 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility165 mg/mLNot Available
LogP-2.912Not Available
Predicted 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
HMDB IDHMDB0001310
DrugBank IDDB01786
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1038581
References
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 ]