Showing metabocard for Leucinic acid (MMDBc0000533)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:39:55 UTC
Update Date2024-04-30 19:32:50 UTC
Metabolite IDMMDBc0000533
Metabolite Identification
Common NameLeucinic acid
DescriptionLeucinic acid, also known as leucic acid, 2-hydroxyisocaproic acid or 2-hydroxy-4-methylvaleric acid, belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. Leucinic acid is a valeric acid derivative having a hydroxy substituent at the 2-position and a methyl substituent at the 4-position. It is an alpha-hydroxy analogue of leucine and a metabolite of the branched-chain amino acid leucine. Leucinic acid is found in all organisms ranging from bacteria to plants to animals. Leucinic acid has been found in a patient with dihydrolipoyl dehydrogenase (DLD) deficiency (PMID: 6688766 ). DLD deficiency is caused by mutations in the DLD gene and is inherited in an autosomal recessive manner. A common feature of dihydrolipoamide dehydrogenase deficiency is a potentially life-threatening buildup of lactic acid in tissues (lactic acidosis), which can cause nausea, vomiting, severe breathing problems, and an abnormal heartbeat. Neurological problems are also common in this condition; the first symptoms in affected infants are often decreased muscle tone (hypotonia) and extreme tiredness (lethargy). As the problems worsen, affected infants can have difficulty feeding, decreased alertness, and seizures. Liver problems can also occur in dihydrolipoamide dehydrogenase deficiency, ranging from an enlarged liver (hepatomegaly) to life-threatening liver failure. In some affected people, liver disease, which can begin anytime from infancy to adulthood, is the primary symptom. Leucinic acid is also present in the urine of patients with short bowel syndrome (PMID: 4018104 )
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x000055e8c4d922b0>


  Mrv1652305271900192D          

  9  8  0  0  0  0            999 V2000
   19.3041  -14.9261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7330  -14.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0186  -12.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8751  -14.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5896  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3041  -14.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1606  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8751  -14.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0186  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x000055e8c4d922b0>

HMDB0000665
     RDKit          3D
Leucinic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.1048    1.1531    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0190    0.1372    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.2191    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218    0.5301   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3261   -0.4427   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321   -1.7460   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5713    0.0337   -0.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -0.7181   -1.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0482    1.3106   -0.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7297    1.9459   -0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724    0.6880   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5116    1.6021    1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    0.1911    1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -1.3188   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0470   -2.0463    0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429   -1.1916    0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    0.6490   -1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650    1.5197    0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -0.4675    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3632   -2.4156    0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016    1.8052    0.4395 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
  4  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
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  0
  9 21  1  0
M  END
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3D SDF for #<Metabolite:0x000055e8c4d922b0>


  Mrv1652305271900192D          

  9  8  0  0  0  0            999 V2000
   19.3041  -14.9261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7330  -14.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0186  -12.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8751  -14.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5896  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3041  -14.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1606  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8751  -14.9261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0186  -13.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000533

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)

> <INCHI_KEY>
LVRFTAZAXQPQHI-UHFFFAOYSA-N

> <FORMULA>
C6H12O3

> <MOLECULAR_WEIGHT>
132.1577

> <EXACT_MASS>
132.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
13.649767203036058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-4-methylpentanoic acid

> <ALOGPS_LOGP>
0.50

> <JCHEM_LOGP>
0.7822806383333333

> <ALOGPS_LOGS>
-0.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.276112311717824

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.257807082104199

> <JCHEM_PKA_STRONGEST_BASIC>
-3.801045430820605

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
32.513400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
leucate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x000055e8c4d922b0>

HMDB0000665
     RDKit          3D
Leucinic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.1048    1.1531    0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0190    0.1372    0.5011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.2191    0.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2218    0.5301   -0.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3261   -0.4427   -0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321   -1.7460   -0.3772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5713    0.0337   -0.6810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -0.7181   -1.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0482    1.3106   -0.4513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7297    1.9459   -0.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9724    0.6880   -0.3297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5116    1.6021    1.1369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    0.1911    1.5839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -1.3188   -0.9992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0470   -2.0463    0.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6429   -1.1916    0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    0.6490   -1.3428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650    1.5197    0.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -0.4675    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3632   -2.4156    0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9016    1.8052    0.4395 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
  4  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
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  0
  9 21  1  0
M  END
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PDB for #<Metabolite:0x000055e8c4d922b0>

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  O   UNK     0      36.034 -27.862   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      38.702 -26.322   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      37.368 -24.012   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      33.367 -26.322   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      34.701 -25.552   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      36.034 -26.322   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      32.033 -25.552   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      33.367 -27.862   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.368 -25.552   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    9                                                            
CONECT    3    9                                                            
CONECT    4    5    7    8                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    9                                                  
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    2    3    6                                                  
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for #<Metabolite:0x000055e8c4d922b0>

COMPND    HMDB0000665
HETATM    1  C1  UNL     1      -2.105   1.153   0.206  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.019   0.137   0.501  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.539  -1.219   0.097  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.222   0.530  -0.262  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.326  -0.443  -0.005  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.032  -1.746  -0.377  1.00  0.00           O  
HETATM    7  C6  UNL     1       2.571   0.034  -0.681  1.00  0.00           C  
HETATM    8  O2  UNL     1       3.187  -0.718  -1.456  1.00  0.00           O  
HETATM    9  O3  UNL     1       3.048   1.311  -0.451  1.00  0.00           O  
HETATM   10  H1  UNL     1      -1.730   1.946  -0.459  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.972   0.688  -0.330  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.512   1.602   1.137  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.806   0.191   1.584  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.386  -1.319  -0.999  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.047  -2.046   0.637  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.643  -1.192   0.285  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.028   0.649  -1.343  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.565   1.520   0.105  1.00  0.00           H  
HETATM   19  H10 UNL     1       1.514  -0.468   1.102  1.00  0.00           H  
HETATM   20  H11 UNL     1       1.363  -2.416   0.269  1.00  0.00           H  
HETATM   21  H12 UNL     1       2.902   1.805   0.439  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    4   13
CONECT    3   14   15   16
CONECT    4    5   17   18
CONECT    5    6    7   19
CONECT    6   20
CONECT    7    8    8    9
CONECT    9   21
END
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SMILES for #<Metabolite:0x000055e8c4d922b0>

CC(C)CC(O)C(O)=O
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INCHI for #<Metabolite:0x000055e8c4d922b0>

InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)
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Synonyms
ValueSource
2-Hydroxyisocaproic acidChEBI
2-Hydroxyisohexanoic acidChEBI
alpha-Hydroxyisocaproic acidChEBI
Leucic acidChEBI
2-HydroxyisocaproateGenerator
2-HydroxyisohexanoateGenerator
a-HydroxyisocaproateGenerator
a-Hydroxyisocaproic acidGenerator
alpha-HydroxyisocaproateGenerator
Α-hydroxyisocaproateGenerator
Α-hydroxyisocaproic acidGenerator
LeucateGenerator
LeucinateGenerator
alpha-Hydroxyisocaproic acid, (R)-isomerHMDB
alpha-Hydroxyisocaproic acid, calcium (2:1) salt, (S)-isomerHMDB
alpha-Hydroxyisocaproic acid, monosodium saltHMDB
alpha-Hydroxyisocaproic acid, (S)-isomerHMDB
2-Hydroxy-4-methyl-valerateHMDB
2-Hydroxy-4-methyl-valeric acidHMDB
2-Hydroxy-4-methylpentanoateHMDB
2-Hydroxy-4-methylpentanoic acidHMDB
2-Hydroxy-4-methylvalerateHMDB
2-Hydroxy-4-methylvaleric acidHMDB
a-Hydroxy-iso-caproateHMDB
a-Hydroxy-iso-caproic acidHMDB
alpha-Hydroxy-iso-caproateHMDB
alpha-Hydroxy-iso-caproic acidHMDB
DL-2-Hydroxy-4-methylpentanoateHMDB
DL-2-Hydroxy-4-methylpentanoic acidHMDB
DL-2-HydroxyisocaproateHMDB
DL-2-Hydroxyisocaproic acidHMDB
DL-a-HydroxyisocaproateHMDB
DL-a-Hydroxyisocaproic acidHMDB
DL-alpha-HydroxyisocaproateHMDB
DL-alpha-Hydroxyisocaproic acidHMDB
DL-LeucateHMDB
DL-Leucic acidHMDB
Leucinic acidChEBI
Molecular FormulaC6H12O3
Average Mass132.1577
Monoisotopic Mass132.07864425
IUPAC Name2-hydroxy-4-methylpentanoic acid
Traditional Nameleucate
CAS Registry NumberNot Available
SMILES
CC(C)CC(O)C(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)
InChI KeyLVRFTAZAXQPQHI-UHFFFAOYSA-N