ChemFOnt: Showing chemical card for Hydroxyisocaproic acid (CFc000000594)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:01 UTC

Chemfont ID

CFc000000594

Molecule Identification

Common Name

Hydroxyisocaproic acid

Definition

Hydroxyisocaproic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-2-Hydroxyisocaproic acid	ChEBI
(+)-alpha-Hydroxyisocaproic acid	ChEBI
(S)-2-Hydroxyisocaproic acid	ChEBI
(S)-Leucic acid	ChEBI
2-HYDROXY-4-methyl-pentanoIC ACID	ChEBI
L-2-Hydroxy-4-methylvaleric acid	ChEBI
L-2-Hydroxyisocaproic acid	ChEBI
L-alpha-Hydroxyisocaproic acid	ChEBI
L-Leucic acid	ChEBI
(+)-2-Hydroxyisocaproate	Generator
(+)-a-Hydroxyisocaproate	Generator
(+)-a-Hydroxyisocaproic acid	Generator
(+)-alpha-Hydroxyisocaproate	Generator
(+)-Α-hydroxyisocaproate	Generator
(+)-Α-hydroxyisocaproic acid	Generator
(S)-2-Hydroxyisocaproate	Generator
(S)-Leucate	Generator
2-HYDROXY-4-methyl-pentanoate	Generator
L-2-Hydroxy-4-methylvalerate	Generator
L-2-Hydroxyisocaproate	Generator
L-a-Hydroxyisocaproate	Generator
L-a-Hydroxyisocaproic acid	Generator
L-alpha-Hydroxyisocaproate	Generator
L-Α-hydroxyisocaproate	Generator
L-Α-hydroxyisocaproic acid	Generator
L-Leucate	Generator
Hydroxyisocaproate	Generator
Hydroxy-isocaproate	HMDB
(2S)-2-Hydroxy-4-methylpentanoate	HMDB
(2S)-2-Hydroxy-4-methylpentanoic acid	HMDB
(S)-2-Hydroxy-4-methyl-pentanoate	HMDB
(S)-2-Hydroxy-4-methyl-pentanoic acid	HMDB
S-2-Hydroxy-4-methylpentanoate	HMDB
S-2-Hydroxy-4-methylpentanoic acid	HMDB

Chemical Formula

C₆H₁₂O₃

Average Molecular Weight

132.1577

Monoisotopic Molecular Weight

132.07864425

IUPAC Name

(2S)-2-hydroxy-4-methylpentanoic acid

Traditional Name

(+)-α-hydroxyisocaproate

CAS Registry Number

13748-90-8

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 Key

LVRFTAZAXQPQHI-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Hydroxy 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 Framework

Aliphatic acyclic compounds

External Descriptors

(2S)-2-hydroxy monocarboxylic acid (CHEBI:44510 )
2-hydroxy-4-methylvaleric acid (CHEBI:44510 )
Hydroxy fatty acids (LMFA01050408 )

Functional Ontology

Physiological effect

Health effect

Observation

Supragingival Plaque (HMDB: HMDB0000746)

Digestive system disorder

Tooth Decay (HMDB: HMDB0000746)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 6422161)
Saliva (PMID: 22308371)
Cerebrospinal Fluid (CSF) (PMID: 6422161)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0000746)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000746)
Feces (PMID: 27275383)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000746)

Source

Endogenous

Endogenous (HMDB: HMDB0000746)

Animal

Animal (HMDB: HMDB0000746)

Microbe

Lactobacillus (HMDB: HMDB0000746)

Exogenous

Food

Food (HMDB: HMDB0000746)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0000746)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000746)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000746)

Lipid metabolism pathway (HMDB: HMDB0000746)

Cellular process

Cell signaling (HMDB: HMDB0000746)

Biochemical process

Lipid transport (HMDB: HMDB0000746)

Role

Biological role

Energy source (HMDB: HMDB0000746)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000746)

Pharmaceutical industry

Biomarker

Maple syrup urine disease (MarkerDB: MDB00000243)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	124 g/L	ALOGPS
logP	0.5	ALOGPS
logP	0.78	ChemAxon
logS	-0.03	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	32.51 m³·mol⁻¹	ChemAxon
Polarizability	13.65 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000746

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022218

KNApSAcK ID

Not Available

Chemspider ID

75520

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Hydroxyisocaproic acid

METLIN ID

5714

PubChem Compound

83697

PDB ID

Not Available

ChEBI ID

44510

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Schmidt, 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.

Showing chemical card for Hydroxyisocaproic acid (CFc000000594)

MOL for CFc000000594 (Hydroxyisocaproic acid)

3D MOL for CFc000000594 (Hydroxyisocaproic acid)

3D SDF for CFc000000594 (Hydroxyisocaproic acid)

3D-SDF for CFc000000594 (Hydroxyisocaproic acid)

PDB for CFc000000594 (Hydroxyisocaproic acid)

3D PDB for CFc000000594 (Hydroxyisocaproic acid)

SMILES for CFc000000594 (Hydroxyisocaproic acid)

INCHI for CFc000000594 (Hydroxyisocaproic acid)

Structure for CFc000000594 (Hydroxyisocaproic acid)

3D Structure for CFc000000594 (Hydroxyisocaproic acid)