isocaproic acid profile

Isocaproic acid, also known as hexanoic acid, is a six-carbon saturated fatty acid with the chemical formula CH3(CH2)4COOH. It is a colorless liquid with a pungent odor and is found naturally in various sources, including cheese, milk, and sweat.

Isocaproic acid is primarily synthesized through the fermentation of carbohydrates by certain bacteria. It is also produced as a byproduct in the industrial production of other chemicals, such as caprolactam.

Isocaproic acid has several effects on the human body. It can act as a signaling molecule, influencing processes like cell growth and inflammation. It is also involved in the production of certain hormones, such as testosterone.

The importance of isocaproic acid lies in its role in various biological processes. It is a crucial component of the human microbiome and plays a role in the digestion and absorption of nutrients. Its presence in sweat contributes to the characteristic body odor.

Isocaproic acid is studied for its potential applications in different fields. For instance, it is being investigated as a potential therapeutic agent for certain diseases, such as inflammatory bowel disease. Its antimicrobial properties are also being explored for use in food preservation and wound healing.

Overall, isocaproic acid is a versatile compound with multiple biological and industrial applications. Research continues to shed light on its multifaceted nature and its potential benefits.'

isocaproic acid: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

isocaproic acid : A methyl-branched fatty acid that is pentanoic acid with a methyl group substituent at position 4. It is a metabolite of 20 alpha-hydroxycholesterol [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	12587
CHEMBL ID	1230308
CHEBI ID	74903
SCHEMBL ID	25603
MeSH ID	M0106383

Synonym
4-02-00-00944 (beilstein handbook reference)
LS-13180
CHEMBL1230308
chebi:74903 ,
isobutylacetic acid
4-methylvaleric acid
nsc4126
pentanoic acid, 4-methyl-
wln: qv2y1&1
4,4-dimethylbutanoic acid
valeric acid, 4-methyl-
isocaproic acid
4-methylpentanoic acid
isohexanoic acid
nsc-4126
646-07-1
3-methylbutane-1-carboxylic acid
brn 1741912
ai3-04161
fema no. 3463
einecs 211-464-0
nsc 4126
inchi=1/c6h12o2/c1-5(2)3-4-6(7)8/h5h,3-4h2,1-2h3,(h,7,8
4-methyl valeric acid
4MV ,
4-methylpentanoic acid, >=98%, fcc, fg
DB03993
LMFA01020076
4-methyl-pentanoic acid
4-methylvaleric acid, 99%
4-methyl-n-valeric acid
BMSE000625
M0750
M0457
HMS1732H05
AKOS000121502
isohexoic acid
4-methyl-valeric acid
STL168053
unii-4g4u8ja28t
4g4u8ja28t ,
FT-0619146
4-methylpentanoic acid [fhfi]
4-methylpentanoic acid [fcc]
4-methylpentanoic acid-1-13c
SCHEMBL25603
4,4-dimethylbutyric acid
DTXSID8060951
344298-98-2
C21399
4-methylpentanoic-d11 acid
J-515800
mfcd00002803
4-methylvaleric acid (isocaproic acid)
Z56347204
iso-caproic acid
4-methyl pentanoic acid
HY-W015882
Q19597905
SY001693
CS-W016598
butyl2,4-dichlorophenoxyacetate
S6278
4-methylpentanoicacid
EN300-16604

Role	Description
human metabolite	Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Class	Description
branched-chain saturated fatty acid	Any saturated fatty acid with a carbon side-chain or isopropyl termination.
methyl-branched fatty acid	Any branched-chain fatty acid containing methyl branches only.
medium-chain fatty acid	Any fatty acid with a chain length of between C6 and C12.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Assay ID	Title	Year	Journal	Article
AID540299	A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis	2010	Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21	Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	15 (41.67)	18.7374
1990's	7 (19.44)	18.2507
2000's	7 (19.44)	29.6817
2010's	5 (13.89)	24.3611
2020's	2 (5.56)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (2.78%)	6.00%
Case Studies	1 (2.78%)	4.05%
Observational	0 (0.00%)	0.25%
Other	34 (94.44%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
octanoic acid octanoic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1764. octanoic acid : A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.	1.96	1	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
glycine [no description available]	1.98	1	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	1.98	1	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
palmitic acid Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.	1.98	1	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor; plant metabolite
phenylpyruvic acid phenylpyruvic acid: RN given refers to parent cpd. phenylpyruvate : A 2-oxo monocarboxylic acid anion resulting from deprotonation of the carboxy group of either keto- or enol-phenylpyruvic acid.. keto-phenylpyruvic acid : A 2-oxo monocarboxylic acid that is 3-phenylpropanoic acid substituted by an oxo group at position 2. It is an intermediate metabolite in the phenylalanine pathway.	1.98	1	2-oxo monocarboxylic acid	chromogenic compound; EC 6.4.1.1 (pyruvate carboxylase) inhibitor; fundamental metabolite
pyruvic acid Pyruvic Acid: An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed). pyruvic acid : A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis.	2.08	1	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
taurine [no description available]	2.25	1	amino sulfonic acid; zwitterion	antioxidant; Escherichia coli metabolite; glycine receptor agonist; human metabolite; mouse metabolite; nutrient; radical scavenger; Saccharomyces cerevisiae metabolite
aminoglutethimide Aminoglutethimide: An aromatase inhibitor that is used in the treatment of advanced BREAST CANCER.. aminoglutethimide : A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.	1.96	1	dicarboximide; piperidones; substituted aniline	adrenergic agent; anticonvulsant; antineoplastic agent; EC 1.14.14.14 (aromatase) inhibitor
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	1.96	1	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
valproic acid Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.	2.21	1	branched-chain fatty acid; branched-chain saturated fatty acid	anticonvulsant; antimanic drug; EC 3.5.1.98 (histone deacetylase) inhibitor; GABA agent; neuroprotective agent; psychotropic drug; teratogenic agent
isoflurane Isoflurane: A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.	2.08	1	organofluorine compound	inhalation anaesthetic
methacetin methacetin: RN given refers to parent cpd. methacetin : A member of the class of acetamides that is paracetamol in which the hydrogen of phenolic hydroxy group has been replaced by a methyl group.	2.03	1	acetamides; aromatic ether
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	2.01	1	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	8.08	5	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
isobutyric acid isobutyric acid: RN given refers to parent cpd. isobutyric acid : A branched fatty acid comprising propanoic acid carrying a methyl branch at C-2.	1.96	1	branched-chain saturated fatty acid; fatty acid 4:0; methyl-branched fatty acid	Daphnia magna metabolite; plant metabolite; volatile oil component
rotenone Derris: A plant genus of the family FABACEAE. The root is a source of rotenoids (ROTENONE) and flavonoids. Some species of Pongamia have been reclassified to this genus and some to MILLETTIA. Some species of Deguelia have been reclassified to this genus.. rotenoid : Members of the class of tetrahydrochromenochromene that consists of a cis-fused tetrahydrochromeno[3,4-b]chromene skeleton and its substituted derivatives. The term was originally restricted to natural products, but is now also used to describe semi-synthetic and fully synthetic compounds.	1.96	1	organic heteropentacyclic compound; rotenones	antineoplastic agent; metabolite; mitochondrial NADH:ubiquinone reductase inhibitor; phytogenic insecticide; piscicide; toxin
2-ethylhexanoic acid 2-ethylhexanoic acid: structure in first source; wood preservative; 2-ethylhexanoic acid is active ingredient in Sinesto B	2.21	1	branched-chain fatty acid
pregnenolone [no description available]	2.89	4	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
isovaleric acid isovaleric acid: structure. isovaleric acid : A C5, branched-chain saturated fatty acid.	2.87	4	branched-chain saturated fatty acid; methylbutyric acid; short-chain fatty acid	mammalian metabolite; plant metabolite
methyl n-butyl ketone Methyl n-Butyl Ketone: An industrial solvent which causes nervous system degeneration. MBK is an acronym often used to refer to it.. hexanone : A ketone that is a hexane carrying an oxo substituent at unspecified position.	1.96	1	ketone
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	1.96	1	benzenes; phenyl acetates
8-hydroxyoctanoic acid 8-hydroxyoctanoic acid: has been identified in the urine of children with medium-chain acyl-CoA dehydrogenase (MCAD) deficiency. 8-hydroxyoctanoic acid : An omega-hydroxy fatty acid that is caprylic acid in which one of the hydrogens of the terminal methyl group is replaced by a hydroxy group.	1.98	1	omega-hydroxy-medium-chain fatty acid; straight-chain fatty acid
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	1.96	1	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
2-aminobicyclo(2,2,1)heptane-2-carboxylic acid 2-aminobicyclo(2,2,1)heptane-2-carboxylic acid: amino acid analog; releases insulin; RN given refers to unlabeled cpd without isomeric designation	1.98	1	monoterpenoid
caprylates Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.	2.37	2	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
(20s)-20-hydroxycholesterol 20-hydroxycholesterol: RN given refers to (20S)-isomer. 20-hydroxycholesterol : An oxysterol that is cholesterol substituted by a hydroxy group at position 20.	2.35	2	20-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid; oxysterol	human metabolite; mouse metabolite
antimycin a Antimycin A: An antibiotic substance produced by Streptomyces species. It inhibits mitochondrial respiration and may deplete cellular levels of ATP. Antimycin A1 has been used as a fungicide, insecticide, and miticide. (From Merck Index, 12th ed). antimycin A : A nine-membered bis-lactone having methyl substituents at the 2- and 6-positions, an n-hexyl substituent at the 8-position, an acyloxy substituent at the 7-position and an aroylamido substituent at the 3-position. It is produced by Streptomyces bacteria and has found commercial use as a fish poison.	1.96	1	amidobenzoic acid
glucagon Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.	1.97	1	peptide hormone
c-peptide C-Peptide: The middle segment of proinsulin that is between the N-terminal B-chain and the C-terminal A-chain. It is a pancreatic peptide of about 31 residues, depending on the species. Upon proteolytic cleavage of proinsulin, equimolar INSULIN and C-peptide are released. C-peptide immunoassay has been used to assess pancreatic beta cell function in diabetic patients with circulating insulin antibodies or exogenous insulin. Half-life of C-peptide is 30 min, almost 8 times that of insulin.	2.01	1

Condition	Relationship Strength	Studies
Dermatitis, Contact, Phototoxic [description not available]	3.17	1
Clostridioides difficile Infection [description not available]	2.68	3
Bowel Diseases, Inflammatory [description not available]	2.25	1
Clostridium Infections Infections with bacteria of the genus CLOSTRIDIUM and closely related CLOSTRIDIOIDES species.	2.68	3
Inflammatory Bowel Diseases Chronic, non-specific inflammation of the GASTROINTESTINAL TRACT. Etiology may be genetic or environmental. This term includes CROHN DISEASE and ULCERATIVE COLITIS.	2.25	1
Autoimmune Diabetes [description not available]	2.44	2
Atrophy, Muscle [description not available]	2.17	1
Diabetes Mellitus, Type 1 A subtype of DIABETES MELLITUS that is characterized by INSULIN deficiency. It is manifested by the sudden onset of severe HYPERGLYCEMIA, rapid progression to DIABETIC KETOACIDOSIS, and DEATH unless treated with insulin. The disease may occur at any age, but is most common in childhood or adolescence.	2.44	2
Muscular Atrophy Derangement in size and number of muscle fibers occurring with aging, reduction in blood supply, or following immobilization, prolonged weightlessness, malnutrition, and particularly in denervation.	2.17	1
Diabetes Mellitus, Adult-Onset [description not available]	2.01	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.01	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.03	1
Overweight A status with BODY WEIGHT that is above certain standards. In the scale of BODY MASS INDEX, overweight is defined as having a BMI of 25.0-29.9 kg/m2. Overweight may or may not be due to increases in body fat (ADIPOSE TISSUE), hence overweight does not equal over fat.	2.03	1
Liver Steatosis [description not available]	2.03	1
Fatty Liver Lipid infiltration of the hepatic parenchymal cells resulting in a yellow-colored liver. The abnormal lipid accumulation is usually in the form of TRIGLYCERIDES, either as a single large droplet or multiple small droplets. Fatty liver is caused by an imbalance in the metabolism of FATTY ACIDS.	2.03	1
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.03	1
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight.	1.96	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.89	4
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	1.98	1
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	1.98	1
Alloxan Diabetes [description not available]	1.98	1

isocaproic acid

Description

Cross-References

Synonyms (65)

Research Excerpts

Roles (1)

Drug Classes (3)

Bioassays (1)

Research

Studies (36)

Market Indicators

Research Demand Index: 30.71

Study Types