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Showing NP-Card for 2-Aminoisobutyric acid (NP0000325)

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Record Information
Version1.0
Created at2006-03-29 12:26:15 UTC
Updated at2021-08-19 23:58:02 UTC
NP-MRD IDNP0000325
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Aminoisobutyric acid
Description2-Aminoisobutyric acid, also known as alpha-methylalanine or a-aminoisobutanoate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 2-Aminoisobutyric acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Aminoisobutyric acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, 2-Aminoisobutyric acid has been detected, but not quantified in cow milk. Aminoisobutyric acid is a nonprotein amino acid (is an end product of pyrimidine metabolism) excreted in the urine of about 5% of healthy individuals (PMID 14806475 ), and high excretion is an autosomal recessive phenotype (PMID 13058271 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000325 (2-Aminoisobutyric acid)


  Mrv1652305261923532D          

  7  6  0  0  0  0            999 V2000
    1.6500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
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3D MOL for NP0000325 (2-Aminoisobutyric acid)

HMDB0001906
     RDKit          3D
2-Aminoisobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    0.0111   -0.4917    1.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532    0.0068   -0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544    1.1387   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -1.1054   -0.9206 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028    0.4723   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890    1.4312    0.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533   -0.0914   -1.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2915   -1.5423    1.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -0.4136    1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6601    0.0902    2.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307    1.8598    0.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1469    1.6121   -1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0179    0.7105    0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9995   -1.7761   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -0.8251   -1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2598   -1.0760   -1.5386 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
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3D SDF for NP0000325 (2-Aminoisobutyric acid)


  Mrv1652305261923532D          

  7  6  0  0  0  0            999 V2000
    1.6500    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000325

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)

> <INCHI_KEY>
FUOOLUPWFVMBKG-UHFFFAOYSA-N

> <FORMULA>
C4H9NO2

> <MOLECULAR_WEIGHT>
103.1198

> <EXACT_MASS>
103.063328537

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
10.328292451659166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-2-methylpropanoic acid

> <ALOGPS_LOGP>
-2.45

> <JCHEM_LOGP>
-2.4082153213259456

> <ALOGPS_LOGS>
0.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.577008004271203

> <JCHEM_PKA_STRONGEST_BASIC>
9.71978792993218

> <JCHEM_POLAR_SURFACE_AREA>
63.32

> <JCHEM_REFRACTIVITY>
25.210600000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.37e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-aminoisobutyric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000325 (2-Aminoisobutyric acid)

HMDB0001906
     RDKit          3D
2-Aminoisobutyric acid
 16 15  0  0  0  0  0  0  0  0999 V2000
    0.0111   -0.4917    1.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0532    0.0068   -0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0544    1.1387   -0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4647   -1.1054   -0.9206 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3028    0.4723   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7890    1.4312    0.1942 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533   -0.0914   -1.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2915   -1.5423    1.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0320   -0.4136    1.7775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6601    0.0902    2.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307    1.8598    0.6813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1469    1.6121   -1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0179    0.7105    0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9995   -1.7761   -0.3377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -0.8251   -1.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2598   -1.0760   -1.5386 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
  2  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  7 16  1  0
M  END
Download

PDB for NP0000325 (2-Aminoisobutyric acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       3.644   0.564   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for NP0000325 (2-Aminoisobutyric acid)

COMPND    HMDB0001906
HETATM    1  C1  UNL     1       0.011  -0.492   1.347  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.053   0.007  -0.082  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.054   1.139  -0.119  1.00  0.00           C  
HETATM    4  N1  UNL     1      -0.465  -1.105  -0.921  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.303   0.472  -0.449  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.789   1.431   0.194  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.053  -0.091  -1.456  1.00  0.00           O  
HETATM    8  H1  UNL     1      -0.291  -1.542   1.441  1.00  0.00           H  
HETATM    9  H2  UNL     1       1.032  -0.414   1.777  1.00  0.00           H  
HETATM   10  H3  UNL     1      -0.660   0.090   2.026  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.731   1.860   0.681  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.147   1.612  -1.097  1.00  0.00           H  
HETATM   13  H6  UNL     1      -2.018   0.710   0.263  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.999  -1.776  -0.338  1.00  0.00           H  
HETATM   15  H8  UNL     1      -1.029  -0.825  -1.730  1.00  0.00           H  
HETATM   16  H9  UNL     1       2.260  -1.076  -1.539  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4    5
CONECT    3   11   12   13
CONECT    4   14   15
CONECT    5    6    6    7
CONECT    7   16
END
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SMILES for NP0000325 (2-Aminoisobutyric acid)

CC(C)(N)C(O)=O
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INCHI for NP0000325 (2-Aminoisobutyric acid)

InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)
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Synonyms
ValueSource
2,2-DimethylglycineChEBI
2-Amino-2-methylpropanoateChEBI
2-Amino-2-methylpropionic acidChEBI
2-MethylalanineChEBI
2MAChEBI
AIBChEBI
alpha,alpha-DimethylglycineChEBI
alpha-Aminoisobutanoic acidChEBI
alpha-Aminoisobutyric acidChEBI
alpha-MethylalanineChEBI
2-Amino-2-methylpropanoic acidGenerator
2-Amino-2-methylpropionateGenerator
a,a-DimethylglycineGenerator
Α,α-dimethylglycineGenerator
a-AminoisobutanoateGenerator
a-Aminoisobutanoic acidGenerator
alpha-AminoisobutanoateGenerator
Α-aminoisobutanoateGenerator
Α-aminoisobutanoic acidGenerator
a-AminoisobutyrateGenerator
a-Aminoisobutyric acidGenerator
alpha-AminoisobutyrateGenerator
Α-aminoisobutyrateGenerator
Α-aminoisobutyric acidGenerator
a-MethylalanineGenerator
Α-methylalanineGenerator
2-AminoisobutyrateGenerator
2-Aminoisobutyric acid, 11C-labeledHMDB
2-Aminoisobutyric acid, 14C-labeledHMDB
2-Amino-isobutyrateHMDB
2-Aminoisobutyric acidKEGG
Chemical FormulaC4H9NO2
Average Mass103.1198 Da
Monoisotopic Mass103.06333 Da
IUPAC Name2-amino-2-methylpropanoic acid
Traditional Nameα-aminoisobutyric acid
CAS Registry Number62-57-7
SMILES
CC(C)(N)C(O)=O
InChI Identifier
InChI=1S/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)
InChI KeyFUOOLUPWFVMBKG-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-07-29View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point335 °CNot Available
Boiling Point204.35 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility181 mg/mL at 25 °CNot Available
LogP-0.163 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility337 g/LALOGPS
logP-2.4ALOGPS
logP-2.4ChemAxon
logS0.51ALOGPS
pKa (Strongest Acidic)2.58ChemAxon
pKa (Strongest Basic)9.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity25.21 m³·mol⁻¹ChemAxon
Polarizability10.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001906
DrugBank IDDB02952
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022732
KNApSAcK IDNot Available
Chemspider ID5891
KEGG Compound IDC03665
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Aminoisobutyric acid
METLIN ID37
PubChem Compound6119
PDB IDNot Available
ChEBI ID27971
Good Scents IDrw1171101
References
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Lucarelli C, Betto P, Ricciarello G, Grossi G: High-performance liquid chromatographic determination of L-3-(3,4-dihydroxyphenyl)-2-methylalanine (alpha-methyldopa) in human urine and plasma. J Chromatogr. 1991 Mar 22;541(1-2):285-96. [PubMed:2037651 ]
  3. HARRIS H: Family studies on the urinary excretion of beta-aminoisobutyric acid. Ann Eugen. 1953 Jun;18(1):43-9. [PubMed:13058271 ]
  4. CRUMPLER HR, DENT CE, HARRIS H, WESTALL RG: beta-Aminoisobutyric acid (alpha-methyl-beta-alanine); a new amino-acid obtained from human urine. Nature. 1951 Feb 24;167(4243):307-8. [PubMed:14806475 ]
  5. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]