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Showing NP-Card for L-Isoleucine (NP0000645)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-01-25 17:01:20 UTC
NP-MRD IDNP0000645
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Isoleucine
DescriptionIsoleucine (Ile) or L-isoleucine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). 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-isolecuine is one of 20 proteinogenic amino acids, i.E., The amino acids used in the biosynthesis of proteins. Isoleucine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aliphatic amino acid. Isoleucine is an essential amino acid in humans, meaning the body cannot synthesize it and that it must be obtained from the diet. In plants and microorganisms, isoleucine is synthesized starting from pyruvate and alpha-ketobutyrate. Isoleucine is classified as a branched chain amino acid (BCAA). BCAAs include three amino acids: Isoleucine, leucine and valine. They are alpha amino acids whose carbon structure is marked by a beta branch point. Despite their structural similarities, BCAAs have different metabolic routes, with valine going solely to carbohydrates (glucogenic), leucine solely to fats (ketogenic) and isoleucine being both a glucogenic and a ketogenic amino acid. Isoleucine is catabolized via with alpha-ketoglutarate where upon it is oxidized and split into propionyl-CoA and acetyl-CoA. Propionyl-CoA is converted into succinyl-CoA, a TCA cycle intermediate which can be converted into oxaloacetate for gluconeogenesis (hence glucogenic). The acetyl-CoA can be fed into the TCA cycle by condensing with oxaloacetate to form citrate or used in the synthesis of ketone bodies or fatty acids. The different metabolism of BCAAs accounts for different requirements for these essential amino acids in humans: 12 Mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine are required respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. BCAAs are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia. An inability to break down isoleucine, along with other amino acids, is associated with maple syrup urine disease (MSUD) (PMID: 34125801 ). Isoleucine, like other BCAAs, is associated with insulin resistance. In particular, higher levels of isoleucine are observed in the blood of diabetic mice, rats, and humans (PMID 25287287 ). Mice fed an isoleucine deprivation diet for one day have improved insulin sensitivity, and feeding of an isoleucine deprivation diet for one week significantly decreases blood glucose levels (PMID: 24684822 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000645 (L-Isoleucine)


  Mrv1652309272007352D          

  9  8  0  0  1  0            999 V2000
    5.2224   -0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.3341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7935   -0.0784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  5  3  1  1  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  6  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000645 (L-Isoleucine)

HMDB0000172
     RDKit          3D
L-Isoleucine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.9483    1.3874   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7094   -0.0928   -0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927   -0.4903   -0.3933 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2345   -2.0164   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.0749    0.5808 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7185    1.5085    0.6256 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0588   -0.3788    0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3447   -1.5974   -0.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704    0.5308   -0.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257    1.5414   -0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637    1.7905    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964    1.9172   -0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9488   -0.4780    0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3631   -0.6450   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0263   -0.2743   -1.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -2.4817   -0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2615   -2.4565   -0.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0471   -2.2815    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5202   -0.3244    1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3611    1.8613   -0.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2068    1.7723    1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789    1.1329    0.5295 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  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  6
  4 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  1
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
Download

3D SDF for NP0000645 (L-Isoleucine)


  Mrv1652309272007352D          

  9  8  0  0  1  0            999 V2000
    5.2224   -0.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.3341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7935   -0.0784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645   -0.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.1592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  5  3  1  1  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  6  0  0  0
  5  9  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000645

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1

> <INCHI_KEY>
AGPKZVBTJJNPAG-WHFBIAKZSA-N

> <FORMULA>
C6H13NO2

> <MOLECULAR_WEIGHT>
131.1729

> <EXACT_MASS>
131.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.11454343235902

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-2-amino-3-methylpentanoic acid

> <ALOGPS_LOGP>
-1.73

> <JCHEM_LOGP>
-1.5084066056000942

> <ALOGPS_LOGS>
-0.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7913082723326537

> <JCHEM_PKA_STRONGEST_BASIC>
9.591345628135606

> <JCHEM_POLAR_SURFACE_AREA>
63.31999999999999

> <JCHEM_REFRACTIVITY>
34.093900000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-isoleucine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000645 (L-Isoleucine)

HMDB0000172
     RDKit          3D
L-Isoleucine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.9483    1.3874   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7094   -0.0928   -0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2927   -0.4903   -0.3933 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2345   -2.0164   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.0749    0.5808 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7185    1.5085    0.6256 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0588   -0.3788    0.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3447   -1.5974   -0.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704    0.5308   -0.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9257    1.5414   -0.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637    1.7905    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1964    1.9172   -0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9488   -0.4780    0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3631   -0.6450   -0.8022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0263   -0.2743   -1.4269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -2.4817   -0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2615   -2.4565   -0.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0471   -2.2815    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5202   -0.3244    1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3611    1.8613   -0.1223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2068    1.7723    1.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4789    1.1329    0.5295 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  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  6
  4 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  1
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
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PDB for NP0000645 (L-Isoleucine)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0       9.748  -0.146   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   2.164   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.081  -1.686   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.748   0.624   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081  -0.146   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414  -0.146   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748   2.164   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080   0.624   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   0.624   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    5                                                            
CONECT    4    5    6    7                                                  
CONECT    5    3    4    9                                                  
CONECT    6    4    8                                                       
CONECT    7    4                                                            
CONECT    8    6                                                            
CONECT    9    1    2    5                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0000645 (L-Isoleucine)

COMPND    HMDB0000172
HETATM    1  C1  UNL     1      -1.948   1.387  -0.202  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.709  -0.093  -0.095  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.293  -0.490  -0.393  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.235  -2.016  -0.239  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.702   0.075   0.581  1.00  0.00           C  
HETATM    6  N1  UNL     1       0.719   1.509   0.626  1.00  0.00           N  
HETATM    7  C6  UNL     1       2.059  -0.379   0.121  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.345  -1.597  -0.016  1.00  0.00           O  
HETATM    9  O2  UNL     1       3.070   0.531  -0.179  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.926   1.541  -0.724  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.064   1.790   0.819  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.196   1.917  -0.811  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.949  -0.478   0.922  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.363  -0.645  -0.802  1.00  0.00           H  
HETATM   15  H6  UNL     1       0.026  -0.274  -1.427  1.00  0.00           H  
HETATM   16  H7  UNL     1       0.410  -2.482  -0.986  1.00  0.00           H  
HETATM   17  H8  UNL     1      -1.262  -2.457  -0.392  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.047  -2.281   0.813  1.00  0.00           H  
HETATM   19  H10 UNL     1       0.520  -0.324   1.596  1.00  0.00           H  
HETATM   20  H11 UNL     1       1.361   1.861  -0.122  1.00  0.00           H  
HETATM   21  H12 UNL     1       1.207   1.772   1.535  1.00  0.00           H  
HETATM   22  H13 UNL     1       3.479   1.133   0.530  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4    5   15
CONECT    4   16   17   18
CONECT    5    6    7   19
CONECT    6   20   21
CONECT    7    8    8    9
CONECT    9   22
END
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SMILES for NP0000645 (L-Isoleucine)

CC[C@H](C)[C@H](N)C(O)=O
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INCHI for NP0000645 (L-Isoleucine)

InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1
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Synonyms
ValueSource
(2S,3S)-2-Amino-3-methylpentanoic acidChEBI
2-Amino-3-methylvaleric acidChEBI
alpha-Amino-beta-methylvaleric acidChEBI
IChEBI
IleChEBI
ISOLEUCINEChEBI
(2S,3S)-2-Amino-3-methylpentanoateGenerator
2-Amino-3-methylvalerateGenerator
a-Amino-b-methylvalerateGenerator
a-Amino-b-methylvaleric acidGenerator
alpha-Amino-beta-methylvalerateGenerator
Α-amino-β-methylvalerateGenerator
Α-amino-β-methylvaleric acidGenerator
(2S,3S)-2-Amino-3-methyl-pentanoateHMDB
(2S,3S)-2-Amino-3-methyl-pentanoic acidHMDB
(2S,3S)-a-Amino-b-methyl-N-valerateHMDB
(2S,3S)-a-Amino-b-methyl-N-valeric acidHMDB
(2S,3S)-a-Amino-b-methylvalerateHMDB
(2S,3S)-a-Amino-b-methylvaleric acidHMDB
(2S,3S)-Alph-amino-beta-methylvalerateHMDB
(2S,3S)-Alph-amino-beta-methylvaleric acidHMDB
(2S,3S)-alpha-Amino-beta-merthyl-N-valerateHMDB
(2S,3S)-alpha-Amino-beta-merthyl-N-valeric acidHMDB
(2S,3S)-alpha-Amino-beta-merthylvalerateHMDB
(2S,3S)-alpha-Amino-beta-merthylvaleric acidHMDB
(2S,3S)-alpha-Amino-beta-methyl-N-valerateHMDB
(2S,3S)-alpha-Amino-beta-methyl-N-valeric acidHMDB
(2S,3S)-alpha-Amino-beta-methylvalerateHMDB
(2S,3S)-alpha-Amino-beta-methylvaleric acidHMDB
(S)-IsoleucineHMDB
(S,S)-IsoleucineHMDB
2-Amino-3-methylpentanoateHMDB
2-Amino-3-methylpentanoic acidHMDB
2S,3S-IsoleucineHMDB
Erythro-L-isoleucineHMDB
Iso-leucineHMDB
L-(+)-IsoleucineHMDB
L-IleHMDB
[S-(R*,r*)]-2-amino-3-methylpentanoateHMDB
[S-(R*,r*)]-2-amino-3-methylpentanoic acidHMDB
Isoleucine, L-isomerHMDB
AlloisoleucineHMDB
Isoleucine, L isomerHMDB
L-Isomer isoleucineHMDB
2S-Amino-3S-methylpentanoateHMDB
L-IsoleucineKEGG
Chemical FormulaC6H13NO2
Average Mass131.1729 Da
Monoisotopic Mass131.09463 Da
IUPAC Name(2S,3S)-2-amino-3-methylpentanoic acid
Traditional NameL-isoleucine
CAS Registry Number73-32-5
SMILES
CC[C@H](C)[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1
InChI KeyAGPKZVBTJJNPAG-WHFBIAKZSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-25View Spectrum
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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)v.dorna83@yahoo.comNot AvailableNot Available2021-08-01View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Abramis bramaFooDB
Achillea millefoliumLOTUS Database
AcipenserFooDB
AcipenseridaeFooDB
Actinidia chinensisFooDB
Agaricus bisporusFooDB
AgaveFooDB
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumFooDB
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Alosa sapidissimaFooDB
Aloysia triphyllaFooDB
AmaranthusFooDB
Amelanchier alnifoliaFooDB
Anacardium occidentaleFooDB
Ananas comosusFooDB
Anarhichas lupusFooDB
AnatidaeFooDB
Anethum graveolensFooDB
Angelica keiskeiFooDB
AnguillaFooDB
AnguilliformesFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anoplopoma fimbriaFooDB
Anthriscus cerefoliumFooDB
Antirrhinum majusLOTUS Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Aplodinotus grunniensFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Archosargus probatocephalusFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemia salinaLOTUS Database
Artemisia dracunculusFooDB
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisFooDB
AstacideaFooDB
Astragalus hamosusLOTUS Database
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Basella albaFooDB
Benincasa hispidaFooDB
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Bison bisonFooDB
BivalviaFooDB
Borago officinalisFooDB
Bos taurusFooDB
BrachyuraFooDB
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaFooDB
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum alicastrumFooDB
Brosme brosmeFooDB
Bubalus bubalisFooDB
BuccinidaeFooDB
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Callinectes sapidusFooDB
Canarium ovatumFooDB
Cancer magisterFooDB
Cannabis sativaCannabisDB
      Not Available
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capra aegagrus hircusFooDB
Capsicum annuumKNApSAcK Database
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carica papaya L.FooDB
CarideaFooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Catha edulisLOTUS Database
Catostomus commersoniiFooDB
Ceratonia siliquaFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chanos chanosFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chionoecetes opilioFooDB
Chlamydomonas reinhardtiiLOTUS Database
Chrysanthemum coronariumFooDB
Cicer arietinumFooDB
CichlidaeFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Claviceps purpureaLOTUS Database
Clupea harengus harengusFooDB
Clupea pallasiiFooDB
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colchicum trigynumLOTUS Database
Colocasia esculentaFooDB
ColumbaFooDB
ColumbidaeFooDB
Corchorus olitoriusFooDB
CoregonusFooDB
Coregonus artediFooDB
Coriandrum sativum L.FooDB
CorylusFooDB
Corylus avellanaFooDB
Crassostrea gigasFooDB
Crassostrea virginicaFooDB
Crateva religiosaFooDB
Crocus sativusFooDB
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita foetidissimaLOTUS Database
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cuminum cyminumFooDB
Curcuma longaFooDB
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Cyprinus carpioFooDB
Daphnia pulexLOTUS Database
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
    • David M. Alabran, and Ahmed F. Mabrouk. Carrot flavor. Sugars and free nitrogenous compounds in f...
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Dromaius novaehollandiaeFooDB
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
EngraulidaeFooDB
Engraulis encrasicolusFooDB
EpinephelusFooDB
Equus caballusFooDB
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eruca vesicaria subsp. SativaFooDB
Esox luciusFooDB
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Euphorbia prostrataLOTUS Database
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Flammulina velutipesFooDB
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
GadiformesFooDB
GadusFooDB
Gadus macrocephalusFooDB
Gadus morhuaFooDB
Garcinia mangostanaFooDB
Gaylussacia baccataFooDB
Ginkgo bilobaFooDB
Gloriosa superbaLOTUS Database
Glycine maxFooDB
GossypiumFooDB
Grifola frondosaFooDB
Hedera hibernicaLOTUS Database
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Hibiscus sabbariffaFooDB
HippoglossusFooDB
Hippoglossus hippoglossusFooDB
Hippoglossus stenolepisFooDB
Hippophae rhamnoidesFooDB
Homarus americanusFooDB
Homo sapiensLOTUS Database
Hoplostethus atlanticusFooDB
Hordeum vulgareFooDB
Hyssopus officinalis L.FooDB
Ictalurus punctatusFooDB
Illicium verumFooDB
Indigofera schimperiLOTUS Database
Iochroma fuchsioidesLOTUS Database
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
Jatropha gossypifoliaLOTUS Database
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Katsuwonus pelamisFooDB
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
LaminariaFooDB
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Leiostomus xanthurusFooDB
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
Lepomis gibbosusFooDB
LeporidaeFooDB
Levisticum officinaleFooDB
Linum usitatissimumFooDB
Litchi chinensisFooDB
Litoria verreauxiiLOTUS Database
Lophius piscatoriusFooDB
Lopholatilus chamaeleonticepsFooDB
Lota lotaFooDB
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
LutjanidaeFooDB
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Medicago sativaFooDB
Meleagris gallopavoFooDB
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Merlangius merlangusFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Micropogonias undulatusFooDB
Microstomus kittFooDB
Molva molvaFooDB
Momordica charantiaFooDB
Morchella deliciosaLOTUS Database
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
Morone saxatilisFooDB
MorusFooDB
Morus nigraFooDB
Mugil cephalusFooDB
Mus musculusLOTUS Database
Musa acuminataFooDB
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
MytilidaeFooDB
Mytilus edulisFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
NephropidaeFooDB
Neptunea antiquaLOTUS Database
Nicotiana tabacumLOTUS Database
Numida meleagrisFooDB
Nuphar luteaFooDB
Ocimum basilicumFooDB
Octopus vulgarisFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
Oncorhynchus gorbuschaFooDB
Oncorhynchus ketaFooDB
Oncorhynchus kisutchFooDB
Oncorhynchus mykissFooDB
Oncorhynchus nerkaFooDB
Oncorhynchus tshawytschaFooDB
Ophiodon elongatusFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia ficus-indicaLOTUS Database
Opuntia macrorhizaFooDB
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
OryctolagusFooDB
Oryza rufipogonFooDB
Oryza sativaFooDB
OsmeridaeFooDB
Osmerus mordaxFooDB
Pachyrhizus erosusFooDB
PalinuridaeFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Paralithodes camtschaticusFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
PectinidaeFooDB
Pediomelum esculentumFooDB
Peprilus triacanthusFooDB
PercoideiFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus densifloraLOTUS Database
Pinus edulisFooDB
Pinus ponderosaLOTUS Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
PleuronectiformesFooDB
Pleurotus ostreatusFooDB
PollachiusFooDB
Pollachius pollachiusFooDB
Polygonum alpinumFooDB
Pomatomus saltatrixFooDB
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Prunus armeniacaFooDB
Prunus aviumFooDB
Prunus avium L.FooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus persicaFooDB
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus tomentosaFooDB
Prunus virginianaFooDB
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Puccinia graminisLOTUS Database
Punica granatumFooDB
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusFooDB
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Reinhardtius hippoglossoidesFooDB
Rheum rhabarbarumFooDB
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
Ripariosida hermaphroditaLOTUS Database
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix pulchraFooDB
Salmo salarFooDB
Salmo trutta forma truttaFooDB
Salmonella entericaLOTUS Database
SalmonidaeFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Satureja hortensis L.FooDB
Satureja montanaFooDB
Scomberomorus cavallaFooDB
Scomberomorus maculatusFooDB
Scophthalmus maximusFooDB
Scorzonera hispanicaFooDB
SebastesFooDB
Sebastes alutusFooDB
Secale cerealeFooDB
Sechium eduleFooDB
Senna obtusifoliaLOTUS Database
SepiidaeFooDB
Seriola lalandiFooDB
Sesamum indicumFooDB
Sesbania bispinosaFooDB
SiluriformesFooDB
Sinapis albaFooDB
SisymbriumFooDB
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
SoleidaeFooDB
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spermacoce pusillaLOTUS Database
Spinacia oleraceaFooDB
SpirulinaFooDB
SqualiformesFooDB
Stellaria mediaLOTUS Database
Stenodus leucichthysFooDB
Stenotomus chrysopsFooDB
Struthio camelusFooDB
Suaeda aegyptiacaLOTUS Database
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Tetragonia tetragonioidesFooDB
TeuthidaFooDB
ThelespermaFooDB
Theobroma cacaoFooDB
Thunnus albacaresFooDB
Thunnus thynnusFooDB
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Trachinotus carolinusFooDB
Trachurus symmetricusFooDB
Tragopogon porrifoliusFooDB
Treculia africanaLOTUS Database
Trigonella foenum-graecumFooDB
Trisopterus esmarkiiFooDB
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Trypanosoma bruceiLOTUS Database
Tsuga heterophyllaLOTUS Database
Typha angustifoliaFooDB
Undaria pinnatifidaFooDB
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
Vaccinium macrocarponFooDB
Vaccinium myrtilloidesFooDB
Vaccinium myrtillusFooDB
Vaccinium ovalifoliumFooDB
Vaccinium ovatumFooDB
Vaccinium oxycoccosFooDB
Vaccinium parvifoliumFooDB
Vaccinium reticulatumFooDB
Vaccinium stamineumFooDB
Vaccinium uliginosumFooDB
Vaccinium vitis-idaeaFooDB
Valeriana officinalisLOTUS Database
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum eduleFooDB
Vicia fabaFooDB
Vicia sativaLOTUS Database
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Virola surinamensisFooDB
Viscum albumLOTUS Database
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis vinifera L.FooDB
Xanthosoma sagittifoliumFooDB
Xiphias gladiusFooDB
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Zoarces americanusFooDB
Species Where Detected
Species NameSourceReference
Escherichia coli K12KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine 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 ParentIsoleucine and derivatives
Alternative Parents
Substituents
  • Isoleucine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point285.5 °CNot Available
Boiling Point225.77 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility35 mg/mLWishart, D. S., Tzur, D., Knox, C., Eisner, R., Guo, A. C., Young, N., ... & Querengesser, L. (2007). HMDB: the human metabolome database. Nucleic acids research, 35(suppl_1), D521-D526.
LogP-1.70Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility114 g/LALOGPS
logP-1.7ALOGPS
logP-1.5ChemAxon
logS-0.06ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)9.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.09 m³·mol⁻¹ChemAxon
Polarizability14.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000172
DrugBank IDDB00167
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012397
KNApSAcK IDC00001374
Chemspider ID6067
KEGG Compound IDC00407
BioCyc IDILE
BiGG ID34887
Wikipedia LinkIsoleucine
METLIN ID5193
PubChem Compound6306
PDB IDNot Available
ChEBI ID17191
Good Scents IDrw1253751
References
General References
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  2. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
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  5. 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 ]
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  7. 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 ]
  8. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
  9. He XY, Yang SY: Roles of type 10 17beta-hydroxysteroid dehydrogenase in intracrinology and metabolism of isoleucine and fatty acids. Endocr Metab Immune Disord Drug Targets. 2006 Mar;6(1):95-102. [PubMed:16611167 ]
  10. Vaalasti A, Suomalainen H, Kuokkanen K, Rechardt L: Neuropeptides in cutaneous neurofibromas of von Recklinghausen's disease. J Cutan Pathol. 1990 Dec;17(6):371-3. [PubMed:1981573 ]
  11. Eriste E, Norberg A, Bonetto V, Nepomuceno D, Lovenberg TW, Sillard R, Jornvall H: A C-terminally elongated form of PHI from porcine intestine. Cell Mol Life Sci. 1999 Nov 15;56(7-8):709-13. [PubMed:11212317 ]
  12. Jalan R, Olde Damink SW, Lui HF, Glabus M, Deutz NE, Hayes PC, Ebmeier K: Oral amino acid load mimicking hemoglobin results in reduced regional cerebral perfusion and deterioration in memory tests in patients with cirrhosis of the liver. Metab Brain Dis. 2003 Mar;18(1):37-49. [PubMed:12603081 ]
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  14. Suk FM, Lin MH, Newman M, Pan S, Chen SH, Liu JD, Shih C: Replication advantage and host factor-independent phenotypes attributable to a common naturally occurring capsid mutation (I97L) in human hepatitis B virus. J Virol. 2002 Dec;76(23):12069-77. [PubMed:12414948 ]
  15. De Miranda J, Panizzutti R, Foltyn VN, Wolosker H: Cofactors of serine racemase that physiologically stimulate the synthesis of the N-methyl-D-aspartate (NMDA) receptor coagonist D-serine. Proc Natl Acad Sci U S A. 2002 Oct 29;99(22):14542-7. Epub 2002 Oct 22. [PubMed:12393813 ]
  16. Blomstrand E, Eliasson J, Karlsson HK, Kohnke R: Branched-chain amino acids activate key enzymes in protein synthesis after physical exercise. J Nutr. 2006 Jan;136(1 Suppl):269S-73S. [PubMed:16365096 ]
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