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Showing NP-Card for L-Alloisoleucine (NP0000697)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:42 UTC
NP-MRD IDNP0000697
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-Alloisoleucine
DescriptionL-alloisoleucine is a branched chain amino acid and is a stereo-isomer of L-isoleucine. It is a common constituent of human plasma (albeit at low levels). L-alloisoleucine is produced as a byproduct of isoleucine transamination. L-Isoleucine is one of the four common amino acids (the 3 others being threonine, hydroxyproline, and hydroxylysine) that have two asymmetric carbon atoms which produce four structural possibilities for the same chemical composition. L-alloisoleucine differs from L-isoleucine by having having different stereochemistry around its beta carbon. Plasma L-alloisoleucine, which is derived from L-isoleucine in vivo, can be used for the diagnosis of maple syrup urine disease (MSUD), a genetic disorder. Indeed, plasma L-alloisoleucine levels above 5 umol/L is the most specific and most sensitive diagnostic marker for all forms of MSUD (PMID: 10508118 ). In MSUD the degradation of the essential branched-chain L-amino acids leucine, valine, and isoleucine and their derived 2-oxoacids is impaired because of an inherited deficiency in branched-chain 2-oxoacid dehydrogenase complex (EC 1.2.4.4) Activity. The accumulation of branched-chain compounds in blood and other body fluids can exert neurotoxic effects.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000697 (L-Alloisoleucine)


  Mrv1652305271900182D          

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

3D MOL for NP0000697 (L-Alloisoleucine)

HMDB0000557
     RDKit          3D
L-Alloisoleucine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.7753   -0.6280    0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    0.2209   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0230    0.8085   -0.4618 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1706    1.6907    0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286   -0.1987   -0.5565 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0610   -0.8659   -1.8493 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1970   -1.1318    0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1940   -2.3646    0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2674   -0.6885    1.8606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4945   -1.7122    0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058   -0.6496    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4887   -0.2570    1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4818   -0.3131   -1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0608    1.0995   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1482    1.4921   -1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2074    2.1032    0.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5224    2.5641    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0826    1.2121    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0874    0.4010   -0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1603   -1.8846   -1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3258   -0.5070   -2.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1934   -0.3911    2.1911 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  6
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
Download

3D SDF for NP0000697 (L-Alloisoleucine)


  Mrv1652305271900182D          

  9  8  0  0  1  0            999 V2000
   -0.1914    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
    1.2375    0.7145    0.0000 C   0  0  1  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
    1.9520    1.1270    0.0000 C   0  0  2  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
    2.6664    0.7145    0.0000 C   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000697

> <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+/m1/s1

> <INCHI_KEY>
AGPKZVBTJJNPAG-UHNVWZDZSA-N

> <FORMULA>
C6H13NO2

> <MOLECULAR_WEIGHT>
131.1729

> <EXACT_MASS>
131.094628665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.23188650969985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-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>
63.32

> <JCHEM_REFRACTIVITY>
34.093900000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
allo-isoleucine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000697 (L-Alloisoleucine)

HMDB0000557
     RDKit          3D
L-Alloisoleucine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.7753   -0.6280    0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521    0.2209   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0230    0.8085   -0.4618 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1706    1.6907    0.7483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286   -0.1987   -0.5565 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0610   -0.8659   -1.8493 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1970   -1.1318    0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1940   -2.3646    0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2674   -0.6885    1.8606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4945   -1.7122    0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058   -0.6496    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4887   -0.2570    1.5394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4818   -0.3131   -1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0608    1.0995   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1482    1.4921   -1.3514 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2074    2.1032    0.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5224    2.5641    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0826    1.2121    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0874    0.4010   -0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1603   -1.8846   -1.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3258   -0.5070   -2.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1934   -0.3911    2.1911 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  6
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
Download

PDB for NP0000697 (L-Alloisoleucine)

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      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -0.206   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  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+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    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0000697 (L-Alloisoleucine)

COMPND    HMDB0000557
HETATM    1  C1  UNL     1      -1.775  -0.628   0.554  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.352   0.221  -0.588  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.023   0.808  -0.462  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.171   1.691   0.748  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.129  -0.199  -0.557  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.061  -0.866  -1.849  1.00  0.00           N  
HETATM    7  C6  UNL     1       1.197  -1.132   0.558  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.194  -2.365   0.365  1.00  0.00           O  
HETATM    9  O2  UNL     1       1.267  -0.688   1.861  1.00  0.00           O  
HETATM   10  H1  UNL     1      -1.495  -1.712   0.422  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.906  -0.650   0.552  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.489  -0.257   1.539  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.482  -0.313  -1.528  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.061   1.100  -0.631  1.00  0.00           H  
HETATM   15  H6  UNL     1       0.148   1.492  -1.351  1.00  0.00           H  
HETATM   16  H7  UNL     1       1.207   2.103   0.726  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.522   2.564   0.606  1.00  0.00           H  
HETATM   18  H9  UNL     1      -0.083   1.212   1.694  1.00  0.00           H  
HETATM   19  H10 UNL     1       2.087   0.401  -0.596  1.00  0.00           H  
HETATM   20  H11 UNL     1       1.160  -1.885  -1.792  1.00  0.00           H  
HETATM   21  H12 UNL     1       0.326  -0.507  -2.462  1.00  0.00           H  
HETATM   22  H13 UNL     1       2.193  -0.391   2.191  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 NP0000697 (L-Alloisoleucine)

CC[C@@H](C)[C@H](N)C(O)=O
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INCHI for NP0000697 (L-Alloisoleucine)

InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5+/m1/s1
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View in JSmol
Synonyms
ValueSource
(2S,3R)-2-Amino-3-methylpentanoic acidChEBI
AlleChEBI
Allo-L-isoleucineChEBI
L(+)-AlloisoleucineChEBI
Threo-3-methyl-L-norvalineChEBI
Threo-L-isoleucineChEBI
(2S,3R)-2-Amino-3-methylpentanoateGenerator
AlloisoleucineHMDB
IsoleucineHMDB
Isoleucine, L isomerHMDB
Isoleucine, L-isomerHMDB
L-IsoleucineHMDB
L-Isomer isoleucineHMDB
(3R)-LS-IsoleucineHMDB
2-Amino-3-methyl-[S-(r*,s*)]-pentanoateHMDB
2-Amino-3-methyl-[S-(r*,s*)]-pentanoic acidHMDB
Allo-isoleucineHMDB
L-Allo-isoleucineHMDB
[S-(R*,s*)]-2-amino-3-methylpentanoateHMDB
[S-(R*,s*)]-2-amino-3-methylpentanoic acidHMDB
Chemical FormulaC6H13NO2
Average Mass131.1729 Da
Monoisotopic Mass131.09463 Da
IUPAC Name(2S,3R)-2-amino-3-methylpentanoic acid
Traditional Nameallo-isoleucine
CAS Registry Number1509-34-8
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+/m1/s1
InChI KeyAGPKZVBTJJNPAG-UHNVWZDZSA-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
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
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 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 Point60 - 64 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility34.4 mg/mL at 25 °CNot Available
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
Polarizability14.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000557
DrugBank IDDB01739
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022117
KNApSAcK IDNot Available
Chemspider ID89698
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound99288
PDB IDNot Available
ChEBI ID43433
Good Scents IDNot Available
References
General References
  1. Korman SH, Andresen BS, Zeharia A, Gutman A, Boneh A, Pitt JJ: 2-ethylhydracrylic aciduria in short/branched-chain acyl-CoA dehydrogenase deficiency: application to diagnosis and implications for the R-pathway of isoleucine oxidation. Clin Chem. 2005 Mar;51(3):610-7. Epub 2004 Dec 22. [PubMed:15615815 ]
  2. Schadewaldt P, Bodner-Leidecker A, Hammen HW, Wendel U: Significance of L-alloisoleucine in plasma for diagnosis of maple syrup urine disease. Clin Chem. 1999 Oct;45(10):1734-40. [PubMed:10508118 ]
  3. Schadewaldt P, Bodner-Leidecker A, Hammen HW, Wendel U: Formation of L-alloisoleucine in vivo: an L-[13C]isoleucine study in man. Pediatr Res. 2000 Feb;47(2):271-7. doi: 10.1203/00006450-200002000-00020. [PubMed:10674358 ]
  4. Bodner-Leidecker A, Wendel U, Saudubray JM, Schadewaldt P: Branched-chain L-amino acid metabolism in classical maple syrup urine disease after orthotopic liver transplantation. J Inherit Metab Dis. 2000 Dec;23(8):805-18. doi: 10.1023/a:1026708618507. [PubMed:11196106 ]
  5. Mamer OA, Reimer ML: On the mechanisms of the formation of L-alloisoleucine and the 2-hydroxy-3-methylvaleric acid stereoisomers from L-isoleucine in maple syrup urine disease patients and in normal humans. J Biol Chem. 1992 Nov 5;267(31):22141-7. [PubMed:1429566 ]