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Showing metabocard for Leucinic acid (HMDB0000665)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-09-22 18:35:06 UTC
HMDB IDHMDB0000665
Secondary Accession Numbers
  • HMDB00665
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
Data?1582752148
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000665 (Leucinic acid)


  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
Download

3D MOL for HMDB0000665 (Leucinic acid)

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
Download

3D SDF for HMDB0000665 (Leucinic acid)


  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>
HMDB0000665

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0000665 (Leucinic acid)

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 HMDB0000665 (Leucinic acid)

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 HMDB0000665 (Leucinic acid)

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 HMDB0000665 (Leucinic acid)

CC(C)CC(O)C(O)=O
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INCHI for HMDB0000665 (Leucinic acid)

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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View in JSmolView NMR AssignmentsView Stereo Labels
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
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
IUPAC Name2-hydroxy-4-methylpentanoic acid
Traditional Nameleucate
CAS Registry Number498-36-2
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point76.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point249.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility886 mg/mLNot Available
LogP0.522 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility124 g/LALOGPS
logP0.5ALOGPS
logP0.78ChemAxon
logS-0.03ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.51 m³·mol⁻¹ChemAxon
Polarizability13.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.63131661259
DarkChem[M-H]-123.83331661259
AllCCS[M+H]+131.97632859911
AllCCS[M-H]-129.50532859911
DeepCCS[M+H]+132.63330932474
DeepCCS[M-H]-129.83830932474
DeepCCS[M-2H]-166.40230932474
DeepCCS[M+Na]+141.26930932474
AllCCS[M+H]+132.032859911
AllCCS[M+H-H2O]+127.932859911
AllCCS[M+NH4]+135.832859911
AllCCS[M+Na]+136.932859911
AllCCS[M-H]-129.532859911
AllCCS[M+Na-2H]-132.332859911
AllCCS[M+HCOO]-135.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.07 minutes32390414
Predicted by Siyang on May 30, 202211.003 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.24 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid61.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1362.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid360.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid100.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid213.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid82.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid401.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid420.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)98.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid768.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid330.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1122.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid248.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid306.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate420.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA281.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water131.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Leucinic acidCC(C)CC(O)C(O)=O2016.2Standard polar33892256
Leucinic acidCC(C)CC(O)C(O)=O1023.9Standard non polar33892256
Leucinic acidCC(C)CC(O)C(O)=O1106.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Leucinic acid,1TMS,isomer #1CC(C)CC(O[Si](C)(C)C)C(=O)O1197.3Semi standard non polar33892256
Leucinic acid,1TMS,isomer #2CC(C)CC(O)C(=O)O[Si](C)(C)C1129.2Semi standard non polar33892256
Leucinic acid,2TMS,isomer #1CC(C)CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1243.6Semi standard non polar33892256
Leucinic acid,1TBDMS,isomer #1CC(C)CC(O[Si](C)(C)C(C)(C)C)C(=O)O1403.1Semi standard non polar33892256
Leucinic acid,1TBDMS,isomer #2CC(C)CC(O)C(=O)O[Si](C)(C)C(C)(C)C1357.2Semi standard non polar33892256
Leucinic acid,2TBDMS,isomer #1CC(C)CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1653.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Leucinic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-0883a44db52a6c25fe992016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leucinic acid GC-MS (2 TMS) - 70eV, Positivesplash10-02gc-9440000000-7fffd162011678b17f4a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leucinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leucinic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leucinic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leucinic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leucinic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leucinic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Leucinic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Leucinic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014r-9000000000-5e0d546d1d0e6bb8c48c2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leucinic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014i-9100000000-ed29dea8a5c4015ec5f92012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leucinic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0a4i-8900000000-44e1b9618ac09f8f20b82012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leucinic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-001r-7900000000-7ab0c9dc80e61fa580c92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leucinic acid LC-ESI-QTOF , negative-QTOFsplash10-001r-7900000000-7ab0c9dc80e61fa580c92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leucinic acid 35V, Negative-QTOFsplash10-000i-9100000000-b13176bdf03a9a3860aa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Leucinic acid 35V, Positive-QTOFsplash10-0006-9000000000-702157a92667487bd5f62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 10V, Positive-QTOFsplash10-00lr-7900000000-d13b28975eefc974bbca2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 20V, Positive-QTOFsplash10-0ap0-9200000000-aaa07e44b97e9617d7f12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-931176b5fcc7e8bde29c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 10V, Negative-QTOFsplash10-001i-4900000000-c818e3e6474333b253262016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 20V, Negative-QTOFsplash10-053i-9200000000-bd611de2f2748fe8a7fa2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 40V, Negative-QTOFsplash10-0ap0-9000000000-4e37e159ea3117d8a5162016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 10V, Negative-QTOFsplash10-0019-9700000000-a7d0b1ce1c211b31bc0d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 20V, Negative-QTOFsplash10-00kr-9100000000-504826b66e199a65ef092021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 40V, Negative-QTOFsplash10-014l-9000000000-ccecb4a470c359949fec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 10V, Positive-QTOFsplash10-014i-9000000000-3019a9d0620e7da019632021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 20V, Positive-QTOFsplash10-00kf-9000000000-e587d44396e53f2409fa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Leucinic acid 40V, Positive-QTOFsplash10-0006-9000000000-457ece1d510dad645c892021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified0-0.39 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Great Plains Labo...
 details
UrineDetected and Quantified0.0 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
 details
UrineDetected and Quantified0-50 umol/mmol creatinineNewborn (0-30 days old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022171
KNApSAcK IDNot Available
Chemspider ID83753
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5635
PubChem Compound92779
PDB IDNot Available
ChEBI ID59783
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1488981
References
Synthesis ReferenceCamien, Merill N.; Fowler, Audree V.; Dunn, Max S. Production of a-hydroxy fatty acids by two strains of Lactobacillus casei. Archives of Biochemistry and Biophysics (1959), 83 408-18.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kuhara T, Shinka T, Inoue Y, Matsumoto M, Yoshino M, Sakaguchi Y, Matsumoto I: Studies of urinary organic acid profiles of a patient with dihydrolipoyl dehydrogenase deficiency. Clin Chim Acta. 1983 Sep 30;133(2):133-40. [PubMed:6688766 ]
  2. Jakobs C, Sweetman L, Nyhan WL: Hydroxy acid metabolites of branched-chain amino acids in amniotic fluid. Clin Chim Acta. 1984 Jul 16;140(2):157-66. [PubMed:6467607 ]
  3. Spaapen LJ, Ketting D, Wadman SK, Bruinvis L, Duran M: Urinary D-4-hydroxyphenyllactate, D-phenyllactate and D-2-hydroxyisocaproate, abnormalities of bacterial origin. J Inherit Metab Dis. 1987;10(4):383-90. [PubMed:3126358 ]
  4. Haan E, Brown G, Bankier A, Mitchell D, Hunt S, Blakey J, Barnes G: Severe illness caused by the products of bacterial metabolism in a child with a short gut. Eur J Pediatr. 1985 May;144(1):63-5. [PubMed:4018104 ]