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Showing metabocard for Hydroxyisocaproic acid (HMDB0000746)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:06 UTC
HMDB IDHMDB0000746
Secondary Accession Numbers
  • HMDB00746
Metabolite 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 ). Hydroxyisocaproic acid has been found to be a metabolite of Lactobacillus and fungal species (http://jultika.oulu.fi/files/isbn9789526211046.pdf).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000746 (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 HMDB0000746 (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 HMDB0000746 (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>
HMDB0000746

> <DATABASE_NAME>
hmdb

> <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 HMDB0000746 (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 HMDB0000746 (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 HMDB0000746 (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 HMDB0000746 (Hydroxyisocaproic acid)

CC(C)C[C@H](O)C(O)=O
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INCHI for HMDB0000746 (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 AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
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
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
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular 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
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg126.05730932474
[M-H]-Not Available126.057http://allccs.zhulab.cn/database/detail?ID=AllCCS00000210
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Supragingival Plaque
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Tooth Decay
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Maple syrup urine disease
  1. Shigematsu Y, Kikuchi K, Momoi T, Sudo M, Kikawa Y, Nosaka K, Kuriyama M, Haruki S, Sanada K, Hamano N, et al.: Organic acids and branched-chain amino acids in body fluids before and after multiple exchange transfusions in maple syrup urine disease. J Inherit Metab Dis. 1983;6(4):183-9. [PubMed:6422161 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000243
Good Scents IDrw1136521
References
Synthesis ReferenceSchmidt, E. G.; Peterson, W. H.; Fred, E. B. The formation of l-leucic acid in the acetone-butyl alcohol fermentation. Journal of Biological Chemistry (1924), 61 163-75.
Material Safety Data Sheet (MSDS)Not Available
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 ]
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