Showing metabocard for (±)-erythro-Isoleucine (MMDBc0000771)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:54:35 UTC
Update Date2024-04-30 19:33:38 UTC
Metabolite IDMMDBc0000771
Metabolite Identification
Common Name(±)-erythro-Isoleucine
Description(±)-erythro-Isoleucine is a flavouring ingredient, dietary supplement, and a nutrient. Branched-chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAA denotes valine, isoleucine, and leucine which are branched chain essential amino acids. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats, and isoleucine to both. The different metabolism 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 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. BCAA are decreased in patients with liver disease such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia, or portacaval shunt. Aromatic amino acids (AAA)-tyrosine, tryptophan, and phenylalanine (as well as methionine) are increased in these conditions. Valine, in particular, has been established as a useful supplemental therapy to the ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. The BCAA are not without side effects. Leucine alone, for example, exacerbates pellagra and can cause psychosis in pellagra patients by increasing excretion of niacin in the urine. Leucine may lower brain serotonin and dopamine. 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).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fd0cd5933c8>


  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
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3D MOL for #<Metabolite:0x00007fd0cd5933c8>

HMDB0260302
     RDKit          3D
D-Alloisoleucine
 22 21  0  0  0  0  0  0  0  0999 V2000
    2.2760    0.3127    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0530    0.9745    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1826    0.7337   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469    1.2571   -1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304   -0.7189    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877   -1.0610    1.4614 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6395   -1.1335   -0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -0.9492   -2.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7377   -1.7634   -0.2144 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606    0.7607    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.7730    0.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4117    0.5397   -0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610    0.4674    1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2603    2.0326    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032    1.3163    0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7136    2.0860   -1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802    1.7194   -1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2769    0.5266   -2.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3961   -1.2930   -0.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -1.9702    1.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1976   -0.2986    2.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6663   -2.7659    0.0052 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  0
  4 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fd0cd5933c8>


  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>
MMDBc0000771

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007fd0cd5933c8>

HMDB0260302
     RDKit          3D
D-Alloisoleucine
 22 21  0  0  0  0  0  0  0  0999 V2000
    2.2760    0.3127    0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0530    0.9745    0.8308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1826    0.7337   -0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0469    1.2571   -1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304   -0.7189    0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877   -1.0610    1.4614 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6395   -1.1335   -0.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6571   -0.9492   -2.0154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7377   -1.7634   -0.2144 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606    0.7607    0.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3220   -0.7730    0.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4117    0.5397   -0.8363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8610    0.4674    1.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2603    2.0326    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032    1.3163    0.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7136    2.0860   -1.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9802    1.7194   -1.7493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2769    0.5266   -2.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3961   -1.2930   -0.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020   -1.9702    1.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1976   -0.2986    2.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6663   -2.7659    0.0052 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  0
  4 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  9 22  1  0
M  END
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PDB for #<Metabolite:0x00007fd0cd5933c8>

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 #<Metabolite:0x00007fd0cd5933c8>

COMPND    HMDB0250767
HETATM    1  C1  UNL     1      -1.851  -1.236  -0.109  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.832  -0.751  -1.128  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.036   0.408  -0.620  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.992   1.558  -0.303  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.771   0.107   0.613  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.488   1.317   0.990  1.00  0.00           N  
HETATM    7  C6  UNL     1       1.708  -0.995   0.491  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.325  -2.147   0.191  1.00  0.00           O  
HETATM    9  O2  UNL     1       3.055  -0.790   0.708  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.759  -0.592  -0.094  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.206  -2.233  -0.502  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.424  -1.377   0.889  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.461  -0.376  -1.991  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.241  -1.616  -1.444  1.00  0.00           H  
HETATM   15  H6  UNL     1       0.627   0.761  -1.432  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.889   1.421  -0.942  1.00  0.00           H  
HETATM   17  H8  UNL     1      -0.507   2.528  -0.490  1.00  0.00           H  
HETATM   18  H9  UNL     1      -1.338   1.507   0.754  1.00  0.00           H  
HETATM   19  H10 UNL     1       0.090  -0.114   1.475  1.00  0.00           H  
HETATM   20  H11 UNL     1       2.118   1.555   0.190  1.00  0.00           H  
HETATM   21  H12 UNL     1       0.818   2.115   1.190  1.00  0.00           H  
HETATM   22  H13 UNL     1       3.534  -1.049   1.563  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 #<Metabolite:0x00007fd0cd5933c8>

CCC(C)C(N)C(O)=O
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INCHI for #<Metabolite:0x00007fd0cd5933c8>

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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Synonyms
ValueSource
(+/-)-erythro-formHMDB
(+/-)-isoleucineHMDB
FEMA 3295HMDB
IsoleucineHMDB
2-Amino-3-methylpentanoic acidMeSH
Molecular FormulaC6H13NO2
Average Mass131.1729
Monoisotopic Mass131.094628665
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