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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:55 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
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
(+)-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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Capra aegagrus hircus
Cervidae
Cervus canadensis
Columba
Columbidae
Dromaius novaehollandiae
Equus caballus
Gallus gallus
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Struthio camelus
Sus scrofa
Sus scrofa domestica
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. 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 ]