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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 08:03:50 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 ).
Structure
Thumb
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
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
(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 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
DescriptionThis compound 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point78 - 80 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-866999574fff80fabad1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-02gc-9440000000-7fffd162011678b17f4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-001r-7900000000-716c5f55d60f6894323bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-014s-9000000000-9c50133cdf095ca16a2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00kb-9100000000-dc2c3e9343c9a8e307c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-5900000000-01e9c211c49cea6fc5c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-9300000000-a1f6fc289aa530d63fd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-eb5a5d102c8e756f6834View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-1a66b9767516fbd45630View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06s9-9400000000-cf71f1c20e2a87bbb2b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-11e049c8df5b1a6268c9View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.7 uMNewborn (0-30 days old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.7 uMNewborn (0-30 days old)Not SpecifiedNormal details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected and Quantified6.17 +/- 7.65 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified14 uMNewborn (0-30 days old)FemaleMaple syrup urine disease details
Cerebrospinal Fluid (CSF)Detected and Quantified12.9 uMNewborn (0-30 days old)FemaleMaple syrup urine disease details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified1.855 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified41.5 (3.00-80.00) umol/mmol creatinineChildren (1-13 years old)BothMaple syrup urine disease (MSUD)
    • MetaGene: Metabol...
details
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 ]
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. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
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 ID1LU
ChEBI ID44510
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)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. 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. Mero AA, Ojala T, Hulmi JJ, Puurtinen R, Karila TA, Seppala T: Effects of alfa-hydroxy-isocaproic acid on body composition, DOMS and performance in athletes. J Int Soc Sports Nutr. 2010 Jan 5;7:1. doi: 10.1186/1550-2783-7-1. [PubMed:20051111 ]
  6. 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 ]