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Showing NP-Card for lisoleucine (NP0228177)

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Record Information
Version2.0
Created at2022-09-06 07:43:39 UTC
Updated at2022-09-06 07:43:39 UTC
NP-MRD IDNP0228177
Secondary Accession NumbersNone
Natural Product Identification
Common Namelisoleucine
Description(±)-Erythro-Isoleucine, also known as (+/-)-isoleucine or (+/-)-erythro-form, 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 (±)-erythro-Isoleucine is a very strong basic compound (based on its pKa) (±)-erythro-Isoleucine is a bitter and odorless tasting compound. Outside of the human body, (±)-erythro-Isoleucine is found, on average, in the highest concentration within a few different foods, such as caseins, milk (cow), and beluga whales and in a lower concentration in garden onions, other soy products, and sweet cherries (±)-erythro-Isoleucine has also been detected, but not quantified in, several different foods, such as soursops, oxheart cabbages, alpine sweetvetchs, mugworts, and roselles. This could make (±)-erythro-isoleucine a potential biomarker for the consumption of these foods. The ratio of leucine to other BCAA is greatest in pork, where leucine is 7 to 8 g and the other BCAA together are only 3 to 4 g (http://Www.Dcnutrition.Com). The BCAA are not without side effects. Valine, in particular, has been established as a useful supplemental therapy to the ailing liver. Branched-chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. lisoleucine is found in Antirrhinum majus, Castanea sativa, Catha edulis, Claviceps purpurea, Colchicum trigynum, Daphnia magna, Glycine max, Pogostemon cablin, Puccinia graminis, Stellaria media, Vicia sativa and Viscum album. lisoleucine was first documented in 2000 (PMID: 10944265). Aromatic amino acids (AAA)-tyrosine, tryptophan, and phenylalanine (as well as methionine) are increased in these conditions.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0228177 (lisoleucine)


  Mrv1652305221920182D          

  9  8  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    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
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
M  END
Download

3D MOL for NP0228177 (lisoleucine)

     RDKit          3D

 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.8148   -1.3283    0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -0.0881   -0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3079    0.5843   -0.0232 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2484    1.8493   -0.9204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9811   -0.1220   -0.2391 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0087    0.8297    0.2884 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2388   -1.3586    0.4676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8519   -2.5217    0.1389 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9956   -1.3820    1.6691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7690   -2.2686   -0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056   -1.3183    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2486   -1.3688    1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4659    0.5806   -0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6011   -0.2894   -1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3391    0.9748    1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0471    1.5339   -1.9644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4690    2.5698   -0.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2667    2.2831   -0.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -0.2000   -1.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2580    1.5219   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    1.1745    1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9659   -1.6562    1.6597 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  9  1  0
  7  8  2  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  1
  4 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  6
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
Download

3D SDF for NP0228177 (lisoleucine)


  Mrv1652305221920182D          

  9  8  0  0  0  0            999 V2000
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    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
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0228177

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(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)

> <INCHI_KEY>
AGPKZVBTJJNPAG-UHFFFAOYSA-N

> <FORMULA>
C6H13NO2

> <MOLECULAR_WEIGHT>
131.1729

> <EXACT_MASS>
131.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.185916676854264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
63.32000000000001

> <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

$$$$
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3D-SDF for NP0228177 (lisoleucine)

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PDB for NP0228177 (lisoleucine)
HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -0.206   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  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    4                                                       
CONECT    4    2    3    5                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    8    9                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0228177 (lisoleucine)
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SMILES for NP0228177 (lisoleucine)
CCC(C)C(N)C(O)=O
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INCHI for NP0228177 (lisoleucine)
InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)
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View in JSmol
Synonyms
ValueSource
(+/-)-erythro-formHMDB
(+/-)-isoleucineHMDB
FEMA 3295HMDB
IsoleucineHMDB
2-Amino-3-methylpentanoic acidMeSH
Chemical FormulaC6H13NO2
Average Mass131.1729 Da
Monoisotopic Mass131.09463 Da
IUPAC Name2-amino-3-methylpentanoic acid
Traditional NameL(+)-isoleucine
CAS Registry NumberNot Available
SMILES
CCC(C)C(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)
InChI KeyAGPKZVBTJJNPAG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Antirrhinum majusLOTUS Database
Castanea sativaLOTUS Database
Catha edulisLOTUS Database
Claviceps purpureaLOTUS Database
Colchicum trigynumLOTUS Database
Daphnia magnaLOTUS Database
Glycine maxLOTUS Database
Pogostemon cablinLOTUS Database
Puccinia graminisLOTUS Database
Stellaria mediaLOTUS Database
Vicia sativaLOTUS Database
Viscum albumLOTUS 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
    • 

  • Branched fatty acid
    • 

  • Methyl-branched fatty acid
    • 

  • Fatty acid
    • 

  • Fatty acyl
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organopnictogen compound
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Amine
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability14.19 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033923  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012397  
KNApSAcK IDNot Available
Chemspider ID769  
KEGG Compound IDC16434  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound791  
PDB IDNot Available
ChEBI ID38264  
Good Scents IDNot Available
References
General References
  1. Dalhus B, Gorbitz CH: Structural relationships in crystals accommodating different stereoisomers of 2-amino-3-methylpentanoic acid. Acta Crystallogr B. 2000 Aug;56(Pt 4):720-7. doi: 10.1107/s0108768100002810. [PubMed:10944265  ] 
  2. LOTUS database [Link]