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Showing NP-Card for L-alpha-Aminobutyric acid (NP0000363)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-04-19 09:56:36 UTC
NP-MRD IDNP0000363
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-alpha-Aminobutyric acid
DescriptionL-alpha-Aminobutyric acid, also known as (S)-2-aminobutanoic acid, homoalanine, 2-AABA, or alpha-Aminobutyric acid, is a member of the class of compounds known as L-alpha-amino acids. L-alpha-Amino acids are alpha amino acids which have the L-configuration of the alpha-carbon atom. Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-alpha-Aminobutyric acid is a non-proteogenic amino acid that can be found in the human kidney, in liver tissues, and in most biofluids or excreta (e.G. Feces, breast milk, urine, and blood). Within the cell, L-alpha-aminobutyric acid is primarily located in the cytoplasm. Alpha-Aminobutyric acid is biosynthesized by transamination of oxobutyrate, a metabolite in isoleucine biosynthesis. As a non-proteogenic amino acid, alpha-aminobutyric acid can be used by nonribosomal peptide synthases. One example of a nonribosomal peptide containing alpha-aminobutyric acid is ophthalmic acid, which was first isolated from calf lens. Alpha-Aminobutyric acid is a non-essential amino acid that is primarily derived from the catabolism of methionine, threonine, and serine. High protein diets can result in significantly higher alpha-aminobutyrate levels in plasma (PMID: 26227325 ). Alpha-Aminobutyric acid is elevated in the plasma of children with Reye's syndrome, tyrosinemia, homocystinuria, nonketotic hyperglycinemia, and ornithine transcarbamylase deficiency (PMID: 420125 ). Alpha-Aminobutyric acid is one of the three isomers of aminobutyric acid. The two others are the neurotransmitter gamma-aminobutyric acid (GABA) and beta-aminobutyric acid (BABA) which is known for inducing plant disease resistance.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000363 (L-alpha-Aminobutyric acid)


  Mrv1652305271900182D          

  7  6  0  0  0  0            999 V2000
 9998.9586 9998.7576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2439 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5292 9998.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2439 9999.9944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6740 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3874 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9586 9997.9323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  6  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
Download

3D MOL for NP0000363 (L-alpha-Aminobutyric acid)

HMDB0000452
     RDKit          3D
L-alpha-Aminobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.9230   -0.3615    0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959    0.2472   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4268    0.4670    0.1580 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4127    1.0413   -0.6931 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351   -0.8323    0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646   -1.5681    1.4494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -1.2988    0.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324   -0.1110    1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016   -1.4744    0.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    0.0420    0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2636    1.2203   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -0.3993   -1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258    1.1454    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2700    2.0440   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6212    0.4415   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423   -0.6032    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  1
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
Download

3D SDF for NP0000363 (L-alpha-Aminobutyric acid)


  Mrv1652305271900182D          

  7  6  0  0  0  0            999 V2000
 9998.9586 9998.7576    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2439 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5292 9998.7576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2439 9999.9944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6740 9999.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3874 9998.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9586 9997.9323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  6  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000363

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1

> <INCHI_KEY>
QWCKQJZIFLGMSD-VKHMYHEASA-N

> <FORMULA>
C4H9NO2

> <MOLECULAR_WEIGHT>
103.1198

> <EXACT_MASS>
103.063328537

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.3377399468906

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-aminobutanoic acid

> <ALOGPS_LOGP>
-2.55

> <JCHEM_LOGP>
-2.3181498124844198

> <ALOGPS_LOGS>
0.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.615755119614637

> <JCHEM_PKA_STRONGEST_BASIC>
9.53467345401491

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
25.0213

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.58e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-2-aminobutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000363 (L-alpha-Aminobutyric acid)

HMDB0000452
     RDKit          3D
L-alpha-Aminobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.9230   -0.3615    0.3816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959    0.2472   -0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4268    0.4670    0.1580 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4127    1.0413   -0.6931 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9351   -0.8323    0.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2646   -1.5681    1.4494 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -1.2988    0.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6324   -0.1110    1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9016   -1.4744    0.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9150    0.0420    0.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2636    1.2203   -0.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -0.3993   -1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2258    1.1454    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2700    2.0440   -0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6212    0.4415   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9423   -0.6032    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  1
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
Download

PDB for NP0000363 (L-alpha-Aminobutyric acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8664.7238664.348   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.3898665.117   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8662.0558664.348   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8663.3898666.656   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8666.0588665.117   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8667.3908664.348   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8664.7238662.807   0.000  0.00  0.00           N+0
CONECT    1    2    5    7                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1    6                                                       
CONECT    6    5                                                            
CONECT    7    1                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for NP0000363 (L-alpha-Aminobutyric acid)

COMPND    HMDB0000452
HETATM    1  C1  UNL     1      -1.923  -0.362   0.382  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.896   0.247  -0.540  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.427   0.467   0.158  1.00  0.00           C  
HETATM    4  N1  UNL     1       1.413   1.041  -0.693  1.00  0.00           N  
HETATM    5  C4  UNL     1       0.935  -0.832   0.666  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.265  -1.568   1.449  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.188  -1.299   0.295  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.632  -0.111   1.421  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.902  -1.474   0.203  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.915   0.042   0.094  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.264   1.220  -0.889  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.755  -0.399  -1.433  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.226   1.145   1.012  1.00  0.00           H  
HETATM   14  H7  UNL     1       1.270   2.044  -0.916  1.00  0.00           H  
HETATM   15  H8  UNL     1       1.621   0.442  -1.514  1.00  0.00           H  
HETATM   16  H9  UNL     1       2.942  -0.603   0.305  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4    5   13
CONECT    4   14   15
CONECT    5    6    6    7
CONECT    7   16
END
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SMILES for NP0000363 (L-alpha-Aminobutyric acid)

CC[C@H](N)C(O)=O
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INCHI for NP0000363 (L-alpha-Aminobutyric acid)

InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
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View in JSmol
Synonyms
ValueSource
(-)-2-Aminobutyric acidChEBI
(2S)-2-Aminobutyric acidChEBI
(S)-2-AminobutanoateChEBI
(S)-2-Aminobutanoic acidChEBI
(S)-2-Aminobutyric acidChEBI
L-(+)-2-Aminobutyric acidChEBI
L-2-AminobuttersaeureChEBI
L-2-Aminobutyric acidChEBI
L-alpha-Amino-N-butyric acidChEBI
L-ButyrineChEBI
S-ButyrineChEBI
(-)-2-AminobutyrateGenerator
(2S)-2-AminobutyrateGenerator
(S)-2-AminobutyrateGenerator
L-(+)-2-AminobutyrateGenerator
L-2-AminobutyrateGenerator
L-a-Amino-N-butyrateGenerator
L-a-Amino-N-butyric acidGenerator
L-alpha-Amino-N-butyrateGenerator
L-Α-amino-N-butyrateGenerator
L-Α-amino-N-butyric acidGenerator
L-a-AminobutyrateGenerator
L-a-Aminobutyric acidGenerator
L-alpha-AminobutyrateGenerator
L-Α-aminobutyrateGenerator
L-Α-aminobutyric acidGenerator
(+)-2-AminobutanoateHMDB
(+)-2-Aminobutanoic acidHMDB
(+)-2-Aminobutyric acidHMDB
(+)-alpha-Aminobutyric acidHMDB
(2S)-2-AminobutanoateHMDB
(2S)-2-Aminobutanoic acidHMDB
(S)-(+)-alpha-Aminobutyric acidHMDB
(S)-2-Amino-butanoateHMDB
(S)-2-Amino-butanoic acidHMDB
2-AminobutanoateHMDB
2-Aminobutanoic acidHMDB
2-AminobutyrateHMDB
2S-Amino-butanoateHMDB
2S-Amino-butanoic acidHMDB
alpha-Aminobutyric acidHMDB
L-2-Amino-N-butyric acidHMDB
L-EthylglycineHMDB
Butyrine, (R)-isomerHMDB
2-Aminobutyric acidHMDB
alpha-Aminobutyric acid, (+-)-isomerHMDB
ButyrineHMDB
Butyrine, (S)-isomerHMDB
L-HomoalanineHMDB
alpha-Aminobutyric acid, (S)-isomerHMDB
HomoalanineHMDB
alpha-Aminobutyric acid, (R)-isomerHMDB
Butyrine, (+-)-isomerHMDB
L-2-AminobutanoateHMDB
Chemical FormulaC4H9NO2
Average Mass103.1198 Da
Monoisotopic Mass103.06333 Da
IUPAC Name(2S)-2-aminobutanoic acid
Traditional Name(-)-2-aminobutyric acid
CAS Registry Number1492-24-6
SMILES
CC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyQWCKQJZIFLGMSD-VKHMYHEASA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-11View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-11View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-11View Spectrum
1D NMR[13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-11View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-10-11View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600.133705802 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201.216488466 MHz, CD3OD, simulated)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
Cycas revolutaLOTUS Database
Homo sapiensLOTUS Database
Homo sapiens (Serum)Animalia
Phoma medicaginisFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point291 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility143800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-3.17Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility358 g/LALOGPS
logP-2.6ALOGPS
logP-2.3ChemAxon
logS0.54ALOGPS
pKa (Strongest Acidic)2.62ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.02 m³·mol⁻¹ChemAxon
Polarizability10.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000452
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012537
KNApSAcK IDNot Available
Chemspider ID72524
KEGG Compound IDC02356
BioCyc IDCPD0-1942
BiGG IDNot Available
Wikipedia LinkAlpha-Aminobutyric acid
METLIN ID12
PubChem Compound80283
PDB IDNot Available
ChEBI ID35619
Good Scents IDrw1141141
References
General References
  1. Yang W, Roth KS: Defect in alpha-ketobutyrate metabolism: a new inborn error. Clin Chim Acta. 1985 Jan 30;145(2):173-82. [PubMed:3918815 ]
  2. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
  3. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [PubMed:6198473 ]
  4. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [PubMed:12297216 ]
  5. Le Boucher J, Charret C, Coudray-Lucas C, Giboudeau J, Cynober L: Amino acid determination in biological fluids by automated ion-exchange chromatography: performance of Hitachi L-8500A. Clin Chem. 1997 Aug;43(8 Pt 1):1421-8. [PubMed:9267323 ]
  6. Oishi M, Mochizuki Y, Sanuki E: [Regional cerebral blood flow and cerebrospinal fluid amino acid analysis in elderly dementia]. No To Shinkei. 1998 Nov;50(11):1018-21. [PubMed:9866128 ]
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