propionyl-coenzyme a

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Propionyl-CoA is a crucial intermediate in various metabolic pathways, including the metabolism of branched-chain amino acids (valine, isoleucine, and threonine), odd-chain fatty acids, and the catabolism of certain amino acids like methionine and threonine. It is synthesized from propionate through the action of propionyl-CoA synthetase, an enzyme that utilizes ATP and coenzyme A to convert propionate into propionyl-CoA. Propionyl-CoA is then further metabolized through a series of enzymatic reactions known as the propionate pathway, ultimately leading to the production of succinyl-CoA, which enters the citric acid cycle. The propionate pathway is essential for the complete oxidation of propionate and the generation of energy. Propionyl-CoA is also involved in the biosynthesis of certain essential compounds, such as heme, a component of hemoglobin. The study of propionyl-CoA is important for understanding various metabolic disorders, including propionic acidemia, a rare genetic disorder characterized by the accumulation of propionyl-CoA due to a deficiency in propionyl-CoA carboxylase, an enzyme involved in the propionate pathway. Propionyl-CoA is also studied in relation to other metabolic diseases, such as diabetes and obesity, as it plays a role in lipid metabolism and glucose homeostasis.'

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

Cross-References

ID Source	ID
PubMed CID	92753
CHEBI ID	15539
SCHEMBL ID	25252
MeSH ID	M0053442

Synonyms (39)

Synonym
s-propanoyl-coa
CHEBI:15539
s-propionylcoenzyme a
3'-phosphoadenosine 5'-(3-{(3r)-3-hydroxy-2,2-dimethyl-4-oxo-4-[(3-oxo-3-{[2-(propanoylsulfanyl)ethyl]amino}propyl)amino]butyl} dihydrogen diphosphate)
s-propionyl-coenzym-a
propanoyl-coenzyme a
s-propanoyl-coenzyme a
1vu ,
propionyl coa
n-propionyl coa
9h-purin-6-amine,9-[5-o-[hydroxy[[hydroxy[[(3r)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-[[2-[(1-oxopropyl)thio]ethyl]amino]propyl]amino]butyl]oxy]phosphinyl]oxy]phosphinyl]-3-o-phosphono-beta-d-ribof
coenzyme a, s-propanoate
coenzyme a, s-propionate
317-66-8
C00100
C02843
propionyl-coenzyme a
long-chain acyl-coa
PROPIONYL-COA ,
propionyl coenzyme a
DB02912
s-[2-[3-[[(2r)-4-[[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] propanethioate
unii-h7hqa57v5h
einecs 206-266-6
h7hqa57v5h ,
{[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3r)-3-hydroxy-2,2-dimethyl-3-[(2-{[2-(propanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
gtpl5248
SCHEMBL25252
125527-27-7
LMFA07050364
DTXSID10185594
alpha-methylacetyl-coa
2-methylacetyl-coenzyme a
alpha-methylacetyl-coenzyme a
2-methylacetyl-coa
s-{(3s,5s,9r)-1-[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-3,5-dioxido-10,14-dioxo-2,4,6-trioxa-11,15-diaza-3lambda~5~,5lambda~5~-diphosphaheptadecan-17-yl} propanethioate (non-pr
Q2640914
propionyl-coenzyme a; (acyl-coa); [m+h]+;
propionylcoenzymea

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Escherichia coli metabolite	Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite	Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[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]

Drug Classes (1)

Class	Description
acyl-CoA	A thioester that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any carboxylic acid.
[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]

Pathways (30)

Pathway	Proteins	Compounds
Metabolism	1496	1108
Metabolism of lipids	500	463
Fatty acid metabolism	113	203
alpha-linolenic (omega3) and linoleic (omega6) acid metabolism	10	41
alpha-linolenic acid (ALA) metabolism	10	31
Mitochondrial Fatty Acid Beta-Oxidation	22	60
Propionyl-CoA catabolism	3	9
Peroxisomal lipid metabolism	25	52
Beta-oxidation of pristanoyl-CoA	9	22
Metabolism of steroids	111	135
Bile acid and bile salt metabolism	31	71
Synthesis of bile acids and bile salts	20	68
Synthesis of bile acids and bile salts via 7alpha-hydroxycholesterol	16	44
Amino acid and derivative metabolism	250	260
Branched-chain amino acid catabolism	20	31
Propanoate metabolism ( Propanoate metabolism )	22	22
NAD+ + CoA + (S)-Methyl-malonate semialdehyde => NADH + Propanoyl-CoA + CO2 ( Valine,Leucine and Isoleucine degradation )	1	6
Propanoyl-CoA + Acceptor = Propenoyl-CoA + Reduced acceptor ( Valine,Leucine and Isoleucine degradation )	2	2
Valine,Leucine and Isoleucine degradation ( Valine,Leucine and Isoleucine degradation )	29	36
methylmalonyl pathway	0	9
valine degradation I	0	18
isoleucine degradation I	0	18
superpathway of threonine metabolism	0	34
pyruvate fermentation to propionate I	0	15
Valine, leucine and isoleucine degradation	0	34
Biochemical pathways: part I	0	466
Valproic acid pathway	0	22
Amino acid metabolism	0	94
Beta-alanine biosynthesis II	1	18
Valine degradation	8	17

Research

Studies (194)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	37 (19.07)	18.7374
1990's	36 (18.56)	18.2507
2000's	45 (23.20)	29.6817
2010's	56 (28.87)	24.3611
2020's	20 (10.31)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 54.91

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	54.91 (24.57)
Research Supply Index	5.29 (2.92)
Research Growth Index	4.68 (4.65)
Search Engine Demand Index	91.05 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (54.91)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	9 (4.55%)	6.00%
Case Studies	5 (2.53%)	4.05%
Observational	0 (0.00%)	0.25%
Other	184 (92.93%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
alpha-hydroxyglutarate 2-hydroxyglutarate : A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of 2-hydroxyglutaric acid.. 2-hydroxyglutaric acid : A 2-hydroxydicarboxylic acid that is glutaric acid in which one hydrogen alpha- to a carboxylic acid group is substituted by a hydroxy group.	6.93	1	2-hydroxydicarboxylic acid; dicarboxylic fatty acid	metabolite; mouse metabolite
alpha-ketobutyric acid alpha-ketobutyric acid: RN given refers to parent cpd; structure. 2-oxobutanoic acid : A 2-oxo monocarboxylic acid that is the 2-oxo derivative of butanoic acid.	2.89	4	2-oxo monocarboxylic acid; short-chain fatty acid
acetoacetic acid acetoacetic acid : A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent.	2.01	1	3-oxo fatty acid; ketone body	metabolite
acetic acid Acetic Acid: Product of the oxidation of ethanol and of the destructive distillation of wood. It is used locally, occasionally internally, as a counterirritant and also as a reagent. (Stedman, 26th ed). acetic acid : A simple monocarboxylic acid containing two carbons.	2.39	2	monocarboxylic acid	antimicrobial food preservative; Daphnia magna metabolite; food acidity regulator; protic solvent
carnitine [no description available]	4.71	9	amino-acid betaine	human metabolite; mouse metabolite
aconitic acid Aconitic Acid: A tricarboxylic acid with the formula (COOH)-CH2-C(COOH)=CH-COOH.. aconitic acid : A tricarboxylic acid that is prop-1-ene substituted by carboxy groups at positions 1, 2 and 3.	2.41	1	tricarboxylic acid
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	2.11	1	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
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.	2.4	2	medium-chain fatty acid; straight-chain saturated fatty acid	antibacterial agent; Escherichia coli metabolite; human metabolite
malyl-coenzyme a [no description available]	2.7	3
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	2.49	2	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
methylmalonic acid Methylmalonic Acid: A malonic acid derivative which is a vital intermediate in the metabolism of fat and protein. Abnormalities in methylmalonic acid metabolism lead to methylmalonic aciduria. This metabolic disease is attributed to a block in the enzymatic conversion of methylmalonyl CoA to succinyl CoA.. methylmalonic acid : A dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group.	3.23	6	C4-dicarboxylic acid	human metabolite
2-methylcitric acid 2-methylcitric acid: RN given refers to parent cpd	3.8	10	tricarboxylic acid
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	3.07	5	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
propionaldehyde propionaldehyde: may cause respiratory irritation; RN given refers to parent cpd; structure. propanal : An aldehyde that consists of ethane bearing a formyl substituent. The parent of the class of propanals.	2.01	1	alpha-CH2-containing aldehyde; propanals	Escherichia coli metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	3.76	10	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
glycine [no description available]	2.43	2	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.	2.51	2	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
glyoxylic acid glyoxylic acid: RN given refers to parent cpd. glyoxylic acid : A 2-oxo monocarboxylic acid that is acetic acid bearing an oxo group at the alpha carbon atom.	3.39	7	2-oxo monocarboxylic acid; aldehydic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
hydrogen carbonate Bicarbonates: Inorganic salts that contain the -HCO3 radical. They are an important factor in determining the pH of the blood and the concentration of bicarbonate ions is regulated by the kidney. Levels in the blood are an index of the alkali reserve or buffering capacity.. hydrogencarbonate : The carbon oxoanion resulting from the removal of a proton from carbonic acid.	2.86	4	carbon oxoanion	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
itaconic acid itaconic acid : A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group.	2.41	1	dicarboxylic acid; dicarboxylic fatty acid; olefinic compound	fungal metabolite; human metabolite
malonic acid malonic acid : An alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.. dicarboxylic acid : Any carboxylic acid containing two carboxy groups.	2.37	2	alpha,omega-dicarboxylic acid	human metabolite
malonic semialdehyde malonic semialdehyde: RN given refers to parent cpd; structure given in first source	1.96	1	aldehydic acid
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.49	2	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
niacin Niacin: A water-soluble vitamin of the B complex occurring in various animal and plant tissues. It is required by the body for the formation of coenzymes NAD and NADP. It has PELLAGRA-curative, vasodilating, and antilipemic properties.. vitamin B3 : Any member of a group of vitamers that belong to the chemical structural class called pyridines that exhibit biological activity against vitamin B3 deficiency. Vitamin B3 deficiency causes a condition known as pellagra whose symptoms include depression, dermatitis and diarrhea. The vitamers include nicotinic acid and nicotinamide (and their ionized and salt forms).. nicotinic acid : A pyridinemonocarboxylic acid that is pyridine in which the hydrogen at position 3 is replaced by a carboxy group.	1.96	1	pyridine alkaloid; pyridinemonocarboxylic acid; vitamin B3	antidote; antilipemic drug; EC 3.5.1.19 (nicotinamidase) inhibitor; Escherichia coli metabolite; human urinary metabolite; metabolite; mouse metabolite; plant metabolite; vasodilator agent
oxaloacetic acid Oxaloacetic Acid: A dicarboxylic acid ketone that is an important metabolic intermediate of the CITRIC ACID CYCLE. It can be converted to ASPARTIC ACID by ASPARTATE TRANSAMINASE.. oxaloacetic acid : An oxodicarboxylic acid that is succinic acid bearing a single oxo group.	3.81	3	C4-dicarboxylic acid; oxo dicarboxylic acid	geroprotector; metabolite
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.	1.96	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
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	2.93	4	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
1-propanol 1-Propanol: A colorless liquid made by oxidation of aliphatic hydrocarbons that is used as a solvent and chemical intermediate.. propan-1-ol : The parent member of the class of propan-1-ols that is propane in which a hydrogen of one of the methyl groups is replaced by a hydroxy group.	2.21	1	propan-1-ols; short-chain primary fatty alcohol	metabolite; protic solvent
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	8.92	13	saturated fatty acid; short-chain fatty acid	antifungal drug
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.	4.73	9	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
sarcosine cocobetaine: N-alkyl-betaine; cause of shampoo dermatitis	2.01	1	N-alkylglycine zwitterion; N-alkylglycine; N-methyl-amino acid; N-methylglycines	Escherichia coli metabolite; glycine receptor agonist; glycine transporter 1 inhibitor; human metabolite; mouse metabolite
selenious acid Selenious Acid: A selenium compound with the molecular formula H2SO3. It used as a source of SELENIUM, especially for patients that develop selenium deficiency following prolonged PARENTERAL NUTRITION.	1.96	1	selenium oxoacid
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	2.89	4	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
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.	1.96	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
isoniazid Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).	2.17	1	carbohydrazide	antitubercular agent; drug allergen
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	2.08	1	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	1.96	1	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
serine Serine: A non-essential amino acid occurring in natural form as the L-isomer. It is synthesized from GLYCINE or THREONINE. It is involved in the biosynthesis of PURINES; PYRIMIDINES; and other amino acids.. serine : An alpha-amino acid that is alanine substituted at position 3 by a hydroxy group.	2.01	1	L-alpha-amino acid; proteinogenic amino acid; serine family amino acid; serine zwitterion; serine	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	1.94	1	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
lysine Lysine: An essential amino acid. It is often added to animal feed.. lysine : A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.. L-lysine : An L-alpha-amino acid; the L-isomer of lysine.	4.41	6	aspartate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; lysine; organic molecular entity; proteinogenic amino acid	algal metabolite; anticonvulsant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.69	3	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
edetic acid Edetic Acid: A chelating agent that sequesters a variety of polyvalent cations such as CALCIUM. It is used in pharmaceutical manufacturing and as a food additive.	2.02	1	ethylenediamine derivative; polyamino carboxylic acid; tetracarboxylic acid	anticoagulant; antidote; chelator; copper chelator; geroprotector
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.9	4	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
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.	2.41	2	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
androstenedione Androstenedione: A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL.. androst-4-ene-3,17-dione : A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.	2.72	2	17-oxo steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	1.96	1	lactose
methionine Methionine: A sulfur-containing essential L-amino acid that is important in many body functions.. methionine : A sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4.	1.97	1	aspartate family amino acid; L-alpha-amino acid; methionine zwitterion; methionine; proteinogenic amino acid	antidote to paracetamol poisoning; human metabolite; micronutrient; mouse metabolite; nutraceutical
phenylalanine Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.	1.97	1	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; phenylalanine; proteinogenic amino acid	algal metabolite; EC 3.1.3.1 (alkaline phosphatase) inhibitor; Escherichia coli metabolite; human xenobiotic metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
dithionitrobenzoic acid Dithionitrobenzoic Acid: A standard reagent for the determination of reactive sulfhydryl groups by absorbance measurements. It is used primarily for the determination of sulfhydryl and disulfide groups in proteins. The color produced is due to the formation of a thio anion, 3-carboxyl-4-nitrothiophenolate.. dithionitrobenzoic acid : An organic disulfide that results from the formal oxidative dimerisation of 2-nitro-5-thiobenzoic acid. An indicator used to quantify the number or concentration of thiol groups.	1.99	1	nitrobenzoic acid; organic disulfide	indicator
valine Valine: A branched-chain essential amino acid that has stimulant activity. It promotes muscle growth and tissue repair. It is a precursor in the penicillin biosynthetic pathway.. valine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isopropyl group.. L-valine : The L-enantiomer of valine.	3.77	3	L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid; valine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
threonine Threonine: An essential amino acid occurring naturally in the L-form, which is the active form. It is found in eggs, milk, gelatin, and other proteins.. threonine : An alpha-amino acid in which one of the hydrogens attached to the alpha-carbon of glycine is substituted by a 1-hydroxyethyl group.	3.26	6	amino acid zwitterion; aspartate family amino acid; L-alpha-amino acid; proteinogenic amino acid; threonine	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
isoleucine Isoleucine: An essential branched-chain aliphatic amino acid found in many proteins. It is an isomer of LEUCINE. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels.. isoleucine : A 2-amino-3-methylpentanoic acid having either (2R,3R)- or (2S,3S)-configuration.. L-isoleucine : The L-enantiomer of isoleucine.	3.11	5	aspartate family amino acid; isoleucine; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
3-mercaptopropionic acid 3-Mercaptopropionic Acid: An inhibitor of glutamate decarboxylase. It decreases the GAMMA-AMINOBUTYRIC ACID concentration in the brain, thereby causing convulsions.. 3-mercaptopropanoic acid : A mercaptopropanoic acid that is propanoic acid carrying a sulfanyl group at position 3.	7.45	2	mercaptopropanoic acid	algal metabolite
quinoxalines quinoxaline : A naphthyridine in which the nitrogens are at positions 1 and 4.	1.98	1	mancude organic heterobicyclic parent; naphthyridine; ortho-fused heteroarene
thiodipropionic acid thiodipropionic acid: structure	2.05	1	dicarboxylic acid
pelargonic acid pelargonic acid: K salt acts as cariostatic agent; RN given refers to parent cpd; structure. nonanoic acid : A C9 straight-chain saturated fatty acid which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers.	1.99	1	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antifeedant; Daphnia magna metabolite; plant metabolite
2-methylbutanoic acid 2-methylbutanoic acid: RN given refers to parent cpd without isomeric designation. 2-methylbutyric acid : A methylbutyric acid comprising a butyric acid core carrying a 2-methyl substituent. Produced from amino acid leucine during nutrient starvation in bacteria.	1.96	1	methylbutyric acid	bacterial metabolite; human metabolite
citrulline citrulline : The parent compound of the citrulline class consisting of ornithine having a carbamoyl group at the N(5)-position.	1.96	1	amino acid zwitterion; citrulline	Daphnia magna metabolite; EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; protective agent; Saccharomyces cerevisiae metabolite
margaric acid margaric acid: RN given refers to unlabeled parent cpd. heptadecanoic acid : A C17 saturated fatty acid and trace component of fats in ruminants.	2.41	2	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; mammalian metabolite
gluconic acid gluconic acid: zinc gluconate has anti-inflammatory activity; RN given refers to (D)-isomer; all RRs refers to (D)-isomer unless otherwise noted. ketogluconic acid : A gluconic acid that contains a ketonic carbonyl group.. D-gluconic acid : A gluconic acid having D-configuration.	2.05	1	gluconic acid	chelator; Penicillium metabolite
copper gluconate Gluconates: Derivatives of gluconic acid (the structural formula HOCH2(CHOH)4COOH), including its salts and esters.	2.05	1	organic molecular entity
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	1.96	1	dialdehyde	biomarker
levulinic acid levulinic acid: inhibits 5-aminolevulinic acid dehydratase; RN given refers to parent cpd; structure in Merck Index, 9th ed, #5316. 4-oxopentanoic acid : An oxopentanoic acid with the oxo group in the 4-position.	2.06	1	oxopentanoic acid; straight-chain saturated fatty acid	plant metabolite
2,2-dimethylbutyric acid 2,2-dimethylbutyric acid: structure given in first source; plasma metabolite of simvastatin. 2,2-dimethylbutyric acid : A branched-chain fatty acid and metabolite of the lactone prodrug simvastatin, whose sodium salt is potentially useful for the treatment of thalassaemias and haemoglobinopathies.	2.31	1	dimethylbutyric acid	metabolite
3-ethylphenol [no description available]	2.25	1	phenols
erythromycin Erythromycin: A bacteriostatic antibiotic macrolide produced by Streptomyces erythreus. Erythromycin A is considered its major active component. In sensitive organisms, it inhibits protein synthesis by binding to 50S ribosomal subunits. This binding process inhibits peptidyl transferase activity and interferes with translocation of amino acids during translation and assembly of proteins.. erythromycin : Any of several wide-spectrum macrolide antibiotics obtained from actinomycete Saccharopolyspora erythraea (formerly known as Streptomyces erythraeus).. erythromycin A : An erythromycin that consists of erythronolide A having 2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribo-hexopyranosyl and 3,4,6-trideoxy-3-(dimethylamino)-beta-D-xylo-hexopyranosyl residues attahced at positions 4 and 6 respectively.	3.85	11	cyclic ketone; erythromycin
pentadecanoic acid pentadecanoic acid: in serum as a marker for intake of milk fat. pentadecanoic acid : A straight-chain saturated fatty acid containing fifteen-carbon atoms.	2.21	1	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; food component; human blood serum metabolite; plant metabolite
dithiothreitol 1,4-dimercaptobutane-2,3-diol : A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.. 1,4-dithiothreitol : The threo-diastereomer of 1,4-dimercaptobutane-2,3-diol.	1.99	1	1,4-dimercaptobutane-2,3-diol; butanediols; dithiol; glycol; thiol	chelator; human metabolite; reducing agent
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	3.08	5	dihydrogen
daunorubicin Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.	2	1	aminoglycoside antibiotic; anthracycline; p-quinones; tetracenequinones	antineoplastic agent; bacterial metabolite
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.	3.22	6	benzenes; phenyl acetates
alkenes [no description available]	2.08	1
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.66	3	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
quizalofop-ethyl quizalofop-ethyl: RN given refers to parent cpd. quizalofop-ethyl : A racemate coprising equimolar amounts of quizalofop-P-ethyl and its enantiomer, (S)-quizalofop-ethyl. A proherbicide for quizalofop.. ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate : An ethyl ester resulting from the formal condensation of the carboxy group of 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid with ethanol.	1.98	1	aromatic ether; ethyl ester; organochlorine compound; quinoxaline derivative
4-pentenoic acid 4-pentenoic acid: inhibitor of fatty acid oxidation; RN given refers to parent cpd. pent-4-enoic acid : A pentenoic acid having the double bond at position 4.	1.96	1	pentenoic acid
web 2086 WEB 2086: structure given in first source; PAF antagonist	1.98	1	organonitrogen heterocyclic compound; organosulfur heterocyclic compound
triazoles Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.	1.98	1	1,2,3-triazole
hydracrylic acid 3-hydroxypropionic acid : A 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group.	3.55	8	3-hydroxy monocarboxylic acid; omega-hydroxy-short-chain fatty acid	Escherichia coli metabolite; human metabolite
triheptanoin [no description available]	3.17	1
3-propylphenol 3-propylphenol: insect bait; RN from File CHEMID	2.25	1
n-acetylglutamic acid N-acetylglutamic acid: RN given refers to (L)-isomer. N-acetyl-L-glutamic acid : An N-acyl-L-amino acid that is L-glutamic acid in which one of the amine hydrogens is substituted by an acetyl group.	1.96	1	N-acetyl-L-amino acid; N-acyl-L-glutamic acid	human metabolite; Saccharomyces cerevisiae metabolite
coenzyme a [no description available]	4.05	15	adenosine 3',5'-bisphosphate	coenzyme; Escherichia coli metabolite; mouse metabolite
succinyl-coenzyme a [no description available]	5.11	14	omega-carboxyacyl-CoA	Escherichia coli metabolite; inhibitor; mouse metabolite
acetoacetyl coa [no description available]	2.13	1	3-oxo-fatty acyl-CoA	Escherichia coli metabolite; mouse metabolite
cobalt Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.	2.45	2	cobalt group element atom; metal allergen	micronutrient
propionylcarnitine propionylcarnitine: RN given refers to cpd without isomeric designation	3.76	3	O-acylcarnitine	analgesic; antirheumatic drug; cardiotonic drug; human metabolite; peripheral nervous system drug
beta-hydroxyvaleric acid 3-hydroxypentanoic acid : A short-chain fatty acid that is valeric acid in which one of the methylene hydrogens at position 3 has been replaced by a hydroxy group.	3.31	6	3-hydroxy fatty acid; ketone body; short-chain fatty acid
1-hexadecyl-2-acetyl-glycero-3-phosphocholine Platelet Activating Factor: A phospholipid derivative formed by PLATELETS; BASOPHILS; NEUTROPHILS; MONOCYTES; and MACROPHAGES. It is a potent platelet aggregating agent and inducer of systemic anaphylactic symptoms, including HYPOTENSION; THROMBOCYTOPENIA; NEUTROPENIA; and BRONCHOCONSTRICTION.. 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine : A 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine betaine which has hexadecyl as the alkyl group. PAF is a potent phospholipid activator and mediator of many leukocyte functions, including platelet aggregation, inflammation, and anaphylaxis.	1.98	1	2-acetyl-1-alkyl-sn-glycero-3-phosphocholine	antihypertensive agent; beta-adrenergic antagonist; bronchoconstrictor agent; hematologic agent; vasodilator agent
valerates Valerates: Derivatives of valeric acid, including its salts and esters.	2.38	2	short-chain fatty acid anion; straight-chain saturated fatty acid anion	plant metabolite
1-(carboxymethylthio)tetradecane 1-(carboxymethylthio)tetradecane: structure given in first source; alkylthio acetic acid, non-beta-oxidizable	1.98	1	straight-chain fatty acid
4'-phosphopantetheine D-pantetheine 4'-phosphate : Pantetheine 4'-phosphate with D (R) configuration at the 2' position.	2	1	pantetheine 4'-phosphate	prosthetic group
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.	2.4	2	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
6-deoxyerythronolide b 6-deoxyerythronolide B: Streptomyces erythreus metabolite; presumed intermediate in biosynthesis of erythromycins; structure given in first source	2.71	3	erythronolide
butyryl-coenzyme a [no description available]	5.33	17	butanoyl-CoAs	Escherichia coli metabolite; mouse metabolite
octanoyl-coenzyme a [no description available]	2.59	2
pristanic acid pristanic acid : A branched, long-chain saturated fatty acid composed of pentadecanoic acid having methyl substituents at the 2-, 6-, 10- and 14-positions.	1.98	1	branched-chain saturated fatty acid; long-chain fatty acid; methyl-branched fatty acid	human metabolite
1,10-bis(carboxymethylthiodecane) 1,10-bis(carboxymethylthiodecane): structure given in first source; alkylthio dicarboxylic acid; non-beta-oxidizable & non-omega-oxidizable	1.98	1
isovaleryl-coenzyme a [no description available]	2.4	2	methylbutanoyl-CoA; short-chain fatty acyl-CoA	mouse metabolite
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	3.58	9	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.91	4
pantetheine Pantetheine: An intermediate in the pathway of coenzyme A formation in mammalian liver and some microorganisms.. pantetheine : An amide obtained by formal condensation of the carboxy group of pantothenic acid and the amino group of cysteamine.	2	1	pantetheines; thiol	human metabolite; metabolite; mouse metabolite
acetyl coenzyme a Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.	6.26	46	acyl-CoA	acyl donor; coenzyme; effector; fundamental metabolite
tretinoin Tretinoin: An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).. retinoic acid : A retinoid consisting of 3,7-dimethylnona-2,4,6,8-tetraenoic acid substituted at position 9 by a 2,6,6-trimethylcyclohex-1-en-1-yl group (geometry of the four exocyclic double bonds is not specified).. all-trans-retinoic acid : A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.	2.41	1	retinoic acid; vitamin A	anti-inflammatory agent; antineoplastic agent; antioxidant; AP-1 antagonist; human metabolite; keratolytic drug; retinoic acid receptor agonist; retinoid X receptor agonist; signalling molecule
carboxymethyl-coenzyme a carboxymethyl-coenzyme A: structure given in first source. carboxymethyl-CoA : An S-alkyl-CoA having carboxymethyl as the S-alkyl component.	1.98	1	S-alkyl-CoA	Brassica napus metabolite; EC 2.3.3.1 [citrate (Si)-synthase] inhibitor
epothilone b [no description available]	2.04	1	epothilone; epoxide	antineoplastic agent; apoptosis inducer; microtubule-stabilising agent
epothilone a Epothilones: A group of 16-member MACROLIDES which stabilize MICROTUBULES in a manner similar to PACLITAXEL. They were originally found in the myxobacterium Sorangium cellulosum, now renamed to Polyangium (MYXOCOCCALES).	2.04	1	epothilone; epoxide	antineoplastic agent; metabolite; microtubule-stabilising agent; tubulin modulator
sodium bicarbonate Sodium Bicarbonate: A white, crystalline powder that is commonly used as a pH buffering agent, an electrolyte replenisher, systemic alkalizer and in topical cleansing solutions.	1.98	1	one-carbon compound; organic sodium salt	antacid; food anticaking agent
potassium bicarbonate potassium hydrogencarbonate : A potassium salt that is the monopotassium salt of carbonic acid. It has fungicidal properties and is used in organic farming for the control of powdery mildew and apple scab.	1.94	1	organic salt; potassium salt	antifungal agrochemical; buffer; food acidity regulator; raising agent
flavin-adenine dinucleotide Flavin-Adenine Dinucleotide: A condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972)	1.96	1	flavin adenine dinucleotide; vitamin B2	cofactor; Escherichia coli metabolite; human metabolite; mouse metabolite; prosthetic group
malonyl coenzyme a Malonyl Coenzyme A: A coenzyme A derivative which plays a key role in the fatty acid synthesis in the cytoplasmic and microsomal systems.. omega-carboxyacyl-CoA : An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with one of the carboxy groups of any alpha,omega-dicarboxylic acid.	5.34	18	malonyl-CoAs	EC 2.3.1.21 (carnitine O-palmitoyltransferase) inhibitor; Escherichia coli metabolite; metabolite; mouse metabolite
3-sulfinopropionic acid 3-sulfinopropionic acid: RN given refers to di-Na salt & not in Chemline 8/4/83; RN for parent cpd not in Chemline 8/4/83. 3-sulfinopropionic acid : A monocarboxylic acid that is propionic acid in which one of the methyl hydrogens is replaced by a sulfino group.	7.04	1	monocarboxylic acid; organosulfinic acid
isobutyryl-coenzyme a [no description available]	2.1	1	methyl-branched fatty acyl-CoA; short-chain fatty acyl-CoA	human metabolite; mouse metabolite
glutaryl-coenzyme a [no description available]	2.1	1	glutaryl-CoAs	mouse metabolite
citramalate citramalate: RN given refers to cpd without isomeric designation. citramalate(2-) : A dicarboxylic acid dianion that is obtained by removal of a proton from both of the carboxylic acid groups of citramalic acid.	2.1	1	dicarboxylic acid dianion	human metabolite; plant metabolite
sterigmatocystin [no description available]	2.02	1	sterigmatocystins	metabolite
4-hydroxy-2-nonenal 4-hydroxy-2-nonenal: cytotoxic product from peroxidation of liver microsomal lipids; RN given refers to cpd without isomeric designation. 4-hydroxynon-2-enal : An enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position.. 4-hydroxynonenal : A monounsaturated fatty aldehyde that is nonanal that has undergone dehydrogenation to introduce a double bond at any position in the aliphatic chain and in which a hydrogen at position 4 has been replaced by a hydroxy group.	2.1	1	4-hydroxynon-2-enal; 4-hydroxynonenal
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	7.45	2	chalcogen; nonmetal atom	macronutrient
fumarates Fumarates: Compounds based on fumaric acid.. fumarate(2-) : A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2-)	2.34	2	butenedioate; C4-dicarboxylate	human metabolite; metabolite; Saccharomyces cerevisiae metabolite
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	2.79	3	cysteinium	fundamental metabolite
crotonyl-coenzyme a crotonoyl-CoA : The (E)-isomer of but-2-enoyl-CoA.	3.78	2	but-2-enoyl-CoA
selenium Selenium: An element with the atomic symbol Se, atomic number 34, and atomic weight 78.97. It is an essential micronutrient for mammals and other animals but is toxic in large amounts. Selenium protects intracellular structures against oxidative damage. It is an essential component of GLUTATHIONE PEROXIDASE.	1.96	1	chalcogen; nonmetal atom	micronutrient
tiglyl-coenzyme a 2-methylbut-2-enoyl-coenzyme A : An alk-2-enoyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 2-methylbut-2-enoic acid.	1.98	1	2-enoyl-CoA; monounsaturated fatty acyl-CoA
platenolide i platenolide I: from Streptomyces platensis; RN & N1 from 9th CI; see also platenolide II: 52212-95-0	1.99	1
acryloyl-coenzyme a acryloyl-coenzyme A: used by Clostridium propionicum in the conversion of lactate to propionate. acryloyl-CoA : The S-acryloyl derivative of coenzyme A.	3.19	5	2-enoyl-CoA; monounsaturated fatty acyl-CoA	mouse metabolite
lipstatin lipstatin: isolated from Streptomyces toxytricini; inhibitor of pancreatic lipase; structure given in first source	2.06	1
protylonolide protylonolide: structure in first source. tylactone : A 16-membererd macrolide that is the aglycone of the antibiotic 5-O-beta-D-mycaminosyltylactone.	1.99	1	diol; enone; macrolide	metabolite
valeryl-coenzyme a pentanoyl-CoA : A short-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of pentanoic acid.	2.03	1	short-chain fatty acyl-CoA
phytosterols Phytosterols: A class of organic compounds known as sterols or STEROIDS derived from plants.. phytosterols : Sterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.	2.72	2
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	3.23	6	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite
tylosin [no description available]	1.99	1
methylmalonyl-coenzyme a [no description available]	6.36	30
ginkgolide b [no description available]	1.98	1
vitamin b 12 Vitamin B 12: A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.	3.27	6

Condition	Relationship Strength	Studies
Acidemia Propionic [description not available]	3.17	4
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.31	1
Propionic Acidemia Autosomal recessive metabolic disorder caused by mutations in PROPIONYL-COA CARBOXYLASE genes that result in dysfunction of branch chain amino acids and of the metabolism of certain fatty acids. Neonatal clinical onset is characterized by severe metabolic acidemia accompanied by hyperammonemia, HYPERGLYCEMIA, lethargy, vomiting, HYPOTONIA; and HEPATOMEGALY. Survivors of the neonatal onset propionic acidemia often show developmental retardation, and intolerance to dietary proteins. Late-onset form of the disease shows mild mental and/or developmental retardation, sometimes without metabolic acidemia.	3.17	4
Koch's Disease [description not available]	2.94	3
Tuberculosis Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.	2.94	3
Liver Steatosis [description not available]	2.41	1
Deficiency, Vitamin B 12 [description not available]	2.41	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.	2.41	1
Vitamin B 12 Deficiency A nutritional condition produced by a deficiency of VITAMIN B 12 in the diet, characterized by megaloblastic anemia. Since vitamin B 12 is not present in plants, humans have obtained their supply from animal products, from multivitamin supplements in the form of pills, and as additives to food preparations. A wide variety of neuropsychiatric abnormalities is also seen in vitamin B 12 deficiency and appears to be due to an undefined defect involving myelin synthesis. (From Cecil Textbook of Medicine, 19th ed, p848)	2.41	1
Hepatocellular Carcinoma [description not available]	3.52	4
Cancer of Liver [description not available]	3.52	4
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	3.52	4
Liver Neoplasms Tumors or cancer of the LIVER.	3.52	4
Injury, Myocardial Reperfusion [description not available]	2.6	1
Heart Disease, Ischemic [description not available]	2.6	1
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	2.6	1
African Sleeping Sickness [description not available]	2.25	1
Trypanosomiasis, African A disease endemic among people and animals in Central Africa. It is caused by various species of trypanosomes, particularly T. gambiense and T. rhodesiense. Its second host is the TSETSE FLY. Involvement of the central nervous system produces African sleeping sickness. Nagana is a rapidly fatal trypanosomiasis of horses and other animals.	2.25	1
Amino Acid Metabolism Disorders, Inborn [description not available]	3.7	10
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	2.68	3
Tuberculosis, Drug-Resistant [description not available]	2.17	1
Tuberculosis, Multidrug-Resistant Tuberculosis resistant to chemotherapy with two or more ANTITUBERCULAR AGENTS, including at least ISONIAZID and RIFAMPICIN. The problem of resistance is particularly troublesome in tuberculous OPPORTUNISTIC INFECTIONS associated with HIV INFECTIONS. It requires the use of second line drugs which are more toxic than the first line regimens. TB with isolates that have developed further resistance to at least three of the six classes of second line drugs is defined as EXTENSIVELY DRUG-RESISTANT TUBERCULOSIS.	2.17	1
Hyperammonemia Elevated level of AMMONIA in the blood. It is a sign of defective CATABOLISM of AMINO ACIDS or ammonia to UREA.	2.1	1
Candida Infection [description not available]	2.1	1
Candidiasis Infection with a fungus of the genus CANDIDA. It is usually a superficial infection of the moist areas of the body and is generally caused by CANDIDA ALBICANS. (Dorland, 27th ed)	2.1	1
Aura [description not available]	2.99	1
Epilepsy A disorder characterized by recurrent episodes of paroxysmal brain dysfunction due to a sudden, disorderly, and excessive neuronal discharge. Epilepsy classification systems are generally based upon: (1) clinical features of the seizure episodes (e.g., motor seizure), (2) etiology (e.g., post-traumatic), (3) anatomic site of seizure origin (e.g., frontal lobe seizure), (4) tendency to spread to other structures in the brain, and (5) temporal patterns (e.g., nocturnal epilepsy). (From Adams et al., Principles of Neurology, 6th ed, p313)	2.99	1
Infection, Toxoplasma gondii [description not available]	2.08	1
Toxoplasmosis The acquired form of infection by Toxoplasma gondii in animals and man.	2.08	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)	2.01	1
Electron Transport Chain Deficiencies, Mitochondrial [description not available]	2.42	2
Mitochondrial Diseases Diseases caused by abnormal function of the MITOCHONDRIA. They may be caused by mutations, acquired or inherited, in mitochondrial DNA or in nuclear genes that code for mitochondrial components. They may also be the result of acquired mitochondria dysfunction due to adverse effects of drugs, infections, or other environmental causes.	2.42	2
Inborn Errors of Metabolism [description not available]	3.06	5
Ataxia with Lactic Acidosis 2 [description not available]	2.36	2
Metabolism, Inborn Errors Errors in metabolic processes resulting from inborn genetic mutations that are inherited or acquired in utero.	3.06	5
Deficiency Diseases A condition produced by dietary or metabolic deficiency. The term includes all diseases caused by an insufficient supply of essential nutrients, i.e., protein (or amino acids), vitamins, and minerals. It also includes an inadequacy of calories. (From Dorland, 27th ed; Stedman, 25th ed)	1.98	1
Weight Reduction [description not available]	1.98	1
Weight Loss Decrease in existing BODY WEIGHT.	1.98	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	1.97	1

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