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Showing NP-Card for Hydroxyisocaproic acid (NP0001212)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-17 15:44:33 UTC
NP-MRD IDNP0001212
Secondary Accession NumbersNone
Natural Product Identification
Common NameHydroxyisocaproic acid
DescriptionHydroxyisocaproic acid is an end product of leucine metabolism in human tissues such as muscle and connective tissue. It belongs to 2-hydroxycarboxylic acid group of amino acid metabolites (PMID 6434570 ). Hydroxyisocaproic acid functions as an “anti-catabolite” and is widely used in the body building community. Chronic alpha-hydroxyisocaproic acid treatment of rats has been shown to improve muscle recovery after immobilization-induced atrophy (PMID: 23757407 ). Additionally, a 4-week hydroxyisocaproic acid supplementation of 1.5 G a day was shown to lead to increases in muscle mass during an intensive training period among soccer athletes (PMID: 20051111 ). Hydroxyisocaproic acid has also shown some potential as a topical antibiotic (PMID: 22483561 ). Elevated levels of 2-hydroxyisocaproic acid have been found in the urine of patients with dihydrolipoyl dehydrogenase (E3) deficiency (PMID: 6688766 ). Hydroxyisocaproic acid is also elevated in maple syrup urine disease, a genetic disorder, and has been shown to accelerate lipid peroxidation. It may also be an indicator of oxidative stress (PMID: 11894849 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001212 (Hydroxyisocaproic acid)


  Mrv1652305271900162D          

  9  8  0  0  1  0            999 V2000
   18.4486  -12.8990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8776  -12.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1631  -10.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0196  -12.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7342  -11.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4486  -12.0740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3052  -11.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0196  -12.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1631  -11.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  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 NP0001212 (Hydroxyisocaproic acid)

HMDB0000746
     RDKit          3D
Hydroxyisocaproic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -1.8265    1.4918    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8755    0.3343    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -0.9091   -0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702    0.6011   -0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3699   -0.5250   -0.3475 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8699   -1.7351   -0.7598 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9610   -0.5615    1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665   -1.6339    1.6435 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130    0.5632    1.5810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7373    1.2774    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    2.4687    0.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1086    1.5023   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5924    0.2136    1.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6978   -0.8124   -0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -1.1466   -1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -1.7960    0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8305    1.5169   -0.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0794    0.6896   -1.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2143   -0.2692   -1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2077   -2.5096   -0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0595    1.2396    1.0992 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  6
  6 20  1  0
  9 21  1  0
M  END
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3D SDF for NP0001212 (Hydroxyisocaproic acid)


  Mrv1652305271900162D          

  9  8  0  0  1  0            999 V2000
   18.4486  -12.8990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8776  -12.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1631  -10.8364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0196  -12.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7342  -11.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4486  -12.0740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.3052  -11.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0196  -12.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1631  -11.6615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  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>
NP0001212

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@H](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)/t5-/m0/s1

> <INCHI_KEY>
LVRFTAZAXQPQHI-YFKPBYRVSA-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>
(2S)-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>
(+)-α-hydroxyisocaproate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0001212 (Hydroxyisocaproic acid)

HMDB0000746
     RDKit          3D
Hydroxyisocaproic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -1.8265    1.4918    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8755    0.3343    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -0.9091   -0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3702    0.6011   -0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3699   -0.5250   -0.3475 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8699   -1.7351   -0.7598 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9610   -0.5615    1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665   -1.6339    1.6435 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130    0.5632    1.5810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7373    1.2774    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737    2.4687    0.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1086    1.5023   -0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5924    0.2136    1.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6978   -0.8124   -0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -1.1466   -1.2140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -1.7960    0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8305    1.5169   -0.1163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0794    0.6896   -1.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2143   -0.2692   -1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2077   -2.5096   -0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0595    1.2396    1.0992 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  6
  6 20  1  0
  9 21  1  0
M  END
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PDB for NP0001212 (Hydroxyisocaproic 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      34.437 -24.078   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      37.105 -22.538   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.771 -20.228   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      31.770 -22.538   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.104 -21.768   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      34.437 -22.538   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.436 -21.768   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      31.770 -24.078   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.771 -21.768   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 NP0001212 (Hydroxyisocaproic acid)

COMPND    HMDB0000746
HETATM    1  C1  UNL     1      -1.826   1.492   0.140  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.876   0.334   0.330  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.585  -0.909  -0.173  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.370   0.601  -0.493  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.370  -0.525  -0.348  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.870  -1.735  -0.760  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.961  -0.561   1.001  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.967  -1.634   1.644  1.00  0.00           O  
HETATM    9  O3  UNL     1       2.513   0.563   1.581  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.737   1.277   0.736  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.374   2.469   0.399  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.109   1.502  -0.937  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.592   0.214   1.406  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.698  -0.812  -0.007  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.346  -1.147  -1.214  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.299  -1.796   0.461  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.830   1.517  -0.116  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.079   0.690  -1.539  1.00  0.00           H  
HETATM   19  H10 UNL     1       2.214  -0.269  -1.053  1.00  0.00           H  
HETATM   20  H11 UNL     1       1.208  -2.510  -0.225  1.00  0.00           H  
HETATM   21  H12 UNL     1       3.059   1.240   1.099  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 NP0001212 (Hydroxyisocaproic acid)

CC(C)C[C@H](O)C(O)=O
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INCHI for NP0001212 (Hydroxyisocaproic acid)

InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m0/s1
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View in JSmolView NMR Assignments
Synonyms
ValueSource
(+)-2-Hydroxyisocaproic acidChEBI
(+)-alpha-Hydroxyisocaproic acidChEBI
(S)-2-Hydroxyisocaproic acidChEBI
(S)-Leucic acidChEBI
2-HYDROXY-4-methyl-pentanoIC ACIDChEBI
L-2-Hydroxy-4-methylvaleric acidChEBI
L-2-Hydroxyisocaproic acidChEBI
L-alpha-Hydroxyisocaproic acidChEBI
L-Leucic acidChEBI
(+)-2-HydroxyisocaproateGenerator
(+)-a-HydroxyisocaproateGenerator
(+)-a-Hydroxyisocaproic acidGenerator
(+)-alpha-HydroxyisocaproateGenerator
(+)-Α-hydroxyisocaproateGenerator
(+)-Α-hydroxyisocaproic acidGenerator
(S)-2-HydroxyisocaproateGenerator
(S)-LeucateGenerator
2-HYDROXY-4-methyl-pentanoateGenerator
L-2-Hydroxy-4-methylvalerateGenerator
L-2-HydroxyisocaproateGenerator
L-a-HydroxyisocaproateGenerator
L-a-Hydroxyisocaproic acidGenerator
L-alpha-HydroxyisocaproateGenerator
L-Α-hydroxyisocaproateGenerator
L-Α-hydroxyisocaproic acidGenerator
L-LeucateGenerator
HydroxyisocaproateGenerator
Hydroxy-isocaproateHMDB
(2S)-2-Hydroxy-4-methylpentanoateHMDB
(2S)-2-Hydroxy-4-methylpentanoic acidHMDB
(S)-2-Hydroxy-4-methyl-pentanoateHMDB
(S)-2-Hydroxy-4-methyl-pentanoic acidHMDB
S-2-Hydroxy-4-methylpentanoateHMDB
S-2-Hydroxy-4-methylpentanoic acidHMDB
Chemical FormulaC6H12O3
Average Mass132.1577 Da
Monoisotopic Mass132.07864 Da
IUPAC Name(2S)-2-hydroxy-4-methylpentanoic acid
Traditional Name(+)-α-hydroxyisocaproate
CAS Registry Number13748-90-8
SMILES
CC(C)C[C@H](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)/t5-/m0/s1
InChI KeyLVRFTAZAXQPQHI-YFKPBYRVSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
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 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point78 - 80 °CNot Available
Boiling Point251.31 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility165500 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.710The Good Scents Company Information System
Predicted 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
HMDB IDHMDB0000746
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022218
KNApSAcK IDNot Available
Chemspider ID75520
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Hydroxyisocaproic acid
METLIN ID5714
PubChem Compound83697
PDB IDNot Available
ChEBI ID44510
Good Scents IDrw1136521
References
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. Liebich HM, Forst C: Hydroxycarboxylic and oxocarboxylic acids in urine: products from branched-chain amino acid degradation and from ketogenesis. J Chromatogr. 1984 Aug 10;309(2):225-42. [PubMed:6434570 ]
  3. Fontella FU, Gassen E, Pulrolnik V, Wannmacher CM, Klein AB, Wajner M, Dutra-Filho CS: Stimulation of lipid peroxidation in vitro in rat brain by the metabolites accumulating in maple syrup urine disease. Metab Brain Dis. 2002 Mar;17(1):47-54. [PubMed:11894849 ]
  4. Lang CH, Pruznak A, Navaratnarajah M, Rankine KA, Deiter G, Magne H, Offord EA, Breuille D: Chronic alpha-hydroxyisocaproic acid treatment improves muscle recovery after immobilization-induced atrophy. Am J Physiol Endocrinol Metab. 2013 Aug 1;305(3):E416-28. doi: 10.1152/ajpendo.00618.2012. Epub 2013 Jun 11. [PubMed:23757407 ]
  5. Sakko M, Tjaderhane L, Sorsa T, Hietala P, Jarvinen A, Bowyer P, Rautemaa R: 2-Hydroxyisocaproic acid (HICA): a new potential topical antibacterial agent. Int J Antimicrob Agents. 2012 Jun;39(6):539-40. doi: 10.1016/j.ijantimicag.2012.02.006. Epub 2012 Apr 5. [PubMed:22483561 ]