3-hydroxybutanal profile

3-Hydroxybutanal, also known as 3-hydroxybutyraldehyde, is a four-carbon aldehyde with a hydroxyl group at the third carbon. It is an important intermediate in various metabolic pathways, particularly in the biosynthesis of the ketone body, acetoacetate. This compound is a key player in the regulation of energy metabolism and is studied for its potential role in diabetes, obesity, and neurodegenerative diseases. It is synthesized through the enzymatic reduction of acetoacetate by the enzyme 3-hydroxybutyrate dehydrogenase. 3-Hydroxybutanal has been shown to have various biological effects, including antioxidant activity and anti-inflammatory properties. Its potential therapeutic applications are currently under investigation.'

ID Source	ID
PubMed CID	7897
MeSH ID	M0299723

Synonym
wln: vh1yq1
acetaldol
.beta.-hydroxybutyraldehyde
butanal, 3-hydroxy-
3-hydroxybutanal
oxybutyric aldehyde
nsc-7610
butyraldehyde, 3-hydroxy-
aldol
3-butanolal
107-89-1
oxybutanal
nsc7610
3-hydroxybutyraldehyde
un2839
hsdb 2663
nsc 7610
brn 1735845
einecs 203-530-2
beta-hydroxybutyraldehyde
ai3-18874
aldol [un2839] [poison]
unii-8c6g962b53
8c6g962b53 ,
AKOS006228052
FT-0631603
aldol [mi]
acetaldol [hsdb]
DTXSID2050407
3-hydroxy-butyraldehyde
un 2839
aldol, aldrichcpr
aldol-reaktion
Q223087
EN300-7524303

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	7 (1.09)	18.7374
1990's	5 (0.78)	18.2507
2000's	212 (32.87)	29.6817
2010's	327 (50.70)	24.3611
2020's	94 (14.57)	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	24 (3.72%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	622 (96.28%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
acetoacetic acid acetoacetic acid : A 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent.	2.04	1	3-oxo fatty acid; ketone body	metabolite
4-hydroxybenzaldehyde [no description available]	2.63	2	hydroxybenzaldehyde	EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor; mouse metabolite; plant metabolite
ethylene glycol Ethylene Glycol: A colorless, odorless, viscous dihydroxy alcohol. It has a sweet taste, but is poisonous if ingested. Ethylene glycol is the most important glycol commercially available and is manufactured on a large scale in the United States. It is used as an antifreeze and coolant, in hydraulic fluids, and in the manufacture of low-freezing dynamites and resins.. ethanediol : Any diol that is ethane or substituted ethane carrying two hydroxy groups.. ethylene glycol : A 1,2-glycol compound produced via reaction of ethylene oxide with water.	2.37	2	ethanediol; glycol	metabolite; mouse metabolite; solvent; toxin
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.	4.04	14	aldehyde	carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	5.47	19	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
benzaldehyde [no description available]	3.8	10	benzaldehydes	EC 3.1.1.3 (triacylglycerol lipase) inhibitor; EC 3.5.5.1 (nitrilase) inhibitor; flavouring agent; fragrance; odorant receptor agonist; plant metabolite
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.08	1	halide anion; monoatomic bromine
butyraldehyde [no description available]	2.41	1	butanals	biomarker; Escherichia coli metabolite; mouse metabolite
1-butanol 1-Butanol: A four carbon linear hydrocarbon that has a hydroxy group at position 1.. butan-1-ol : A primary alcohol that is butane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It it produced in small amounts in humans by the gut microbes.	2.08	1	alkyl alcohol; primary alcohol; short-chain primary fatty alcohol	human metabolite; mouse metabolite; protic solvent
carbamates [no description available]	2.7	3	amino-acid anion
carbon monoxide Carbon Monoxide: Carbon monoxide (CO). A poisonous colorless, odorless, tasteless gas. It combines with hemoglobin to form carboxyhemoglobin, which has no oxygen carrying capacity. The resultant oxygen deprivation causes headache, dizziness, decreased pulse and respiratory rates, unconsciousness, and death. (From Merck Index, 11th ed). carbon monoxide : A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas.	2.41	1	carbon oxide; gas molecular entity; one-carbon compound	biomarker; EC 1.9.3.1 (cytochrome c oxidase) inhibitor; human metabolite; ligand; metabolite; mitochondrial respiratory-chain inhibitor; mouse metabolite; neurotoxin; neurotransmitter; P450 inhibitor; probe; signalling molecule; vasodilator agent
catechol [no description available]	2.1	1	catechols	allelochemical; genotoxin; plant metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	3.31	6	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
chloroacetic acid chloroacetic acid: urinary metabolite of vinyl chloride; RN given refers to parent cpd; structure. chloroacetic acid : A chlorocarboxylic acid that is acetic acid carrying a 2-chloro substituent.	2.02	1	chlorocarboxylic acid; haloacetic acid	alkylating agent; herbicide
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.	2.49	2	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
chlorine chloride : A halide anion formed when chlorine picks up an electron to form an an anion.	2.98	4	halide anion; monoatomic chlorine	cofactor; Escherichia coli metabolite; human metabolite
coumarin 2H-chromen-2-one: coumarin derivative	2.52	2	coumarins	fluorescent dye; human metabolite; plant metabolite
2-aminoacetaldehyde 2-aminoacetaldehyde: structure. 2-aminoacetaldehyde : An amino aldehyde that is acetaldehyde in which one of the hydrogens of the methyl group has been replaced by an amino group.	2.05	1	amino aldehyde; omega-aminoaldehyde	Escherichia coli metabolite
nornicotine nornicotine: agricultural or horticultural insecticide; RN given refers to (+-)-isomer; structure	2.41	1
phosphonoacetaldehyde phosphonoacetaldehyde : A phosphonic acid consisting of acetaldehyde with the phospho group at the 2-position.	1.99	1	phosphonic acids	mouse metabolite
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.	2.6	1	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.	2.03	1	alpha-CH2-containing aldehyde; propanals	Escherichia coli metabolite
4-nitrobenzaldehyde 4-nitrobenzaldehyde: RN given refers to parent cpd. 4-nitrobenzaldehyde : A C-nitro compound that is benzaldehyde substituted at the para-position with a nitro group.	3.77	10	benzaldehydes; C-nitro compound
phosphonoacetic acid Phosphonoacetic Acid: A simple organophosphorus compound that inhibits DNA polymerase, especially in viruses and is used as an antiviral agent.. phosphonoacetic acid : A member of the class of phosphonic acids that is phosphonic acid in which the hydrogen attached to the phosphorous is replaced by a carboxymethyl group.	2.07	1	monocarboxylic acid; phosphonic acids	antiviral agent; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor
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.	2.46	2	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dihydroxyacetone phosphate Dihydroxyacetone Phosphate: An important intermediate in lipid biosynthesis and in glycolysis.. dihydroxyacetone phosphate : A member of the class of glycerone phosphates that consists of glycerone bearing a single phospho substituent.	2.98	4	glycerone phosphates; primary alpha-hydroxy ketone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dihydroxyacetone [no description available]	3.3	6	ketotriose; primary alpha-hydroxy ketone	antifungal agent; Escherichia coli metabolite; human metabolite; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
dimethyl sulfoxide Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.	2.51	2	sulfoxide; volatile organic compound	alkylating agent; antidote; Escherichia coli metabolite; geroprotector; MRI contrast agent; non-narcotic analgesic; polar aprotic solvent; radical scavenger
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	3.71	10	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
glycine [no description available]	3.32	6	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
glyceraldehyde Glyceraldehyde: An aldotriose containing the propionaldehyde structure with hydroxy groups at the 2- and 3-positions. It is involved in the formation of ADVANCED GLYCOSYLATION END PRODUCTS.. glyceraldehyde : An aldotriose comprising propanal having hydroxy groups at the 2- and 3-positions. It plays role in the formation of advanced glycation end-products (AGEs), a deleterious accompaniment to ageing.. aldose : Aldehydic parent sugars (polyhydroxy aldehydes H[CH(OH)]nC(=O)H, n >= 2) and their intramolecular hemiacetals.	2.05	1	aldotriose	fundamental metabolite
glycerol Moon: The natural satellite of the planet Earth. It includes the lunar cycles or phases, the lunar month, lunar landscapes, geography, and soil.	2.06	1	alditol; triol	algal metabolite; detergent; Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; solvent
glycolaldehyde [no description available]	2.51	2	glycolaldehydes	fundamental metabolite; human metabolite
glycolic acid glycolic acid: RN given refers to parent cpd. glycolic acid : A 2-hydroxy monocarboxylic acid that is acetic acid where the methyl group has been hydroxylated.	2.93	4	2-hydroxy monocarboxylic acid; primary alcohol	keratolytic drug; metabolite
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.	2.48	2	2-oxo monocarboxylic acid; aldehydic acid	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	3.47	7	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
imidazole imidazole: RN given refers to parent cpd. 1H-imidazole : An imidazole tautomer which has the migrating hydrogen at position 1.	2.77	3	imidazole
pipecolic acid pipecolic acid: RN given refers to cpd without isomeric designation. pipecolic acid : A piperidinemonocarboxylic acid in which the carboxy group is located at position C-2.. pipecolate : A piperidinecarboxylate that is the conjugate base of pipecolic acid.	2.07	1	piperidinemonocarboxylic acid
lactaldehyde lactaldehyde : A member of the class of propanals obtained by the reduction of the carboxylic group of lactic acid (2-hydroxypropanoic acid).	2.04	1	hydroxyaldehyde; propanals	mouse metabolite
pyruvaldehyde Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals.. methylglyoxal : A 2-oxo aldehyde derived from propanal.	2.15	1	2-oxo aldehyde; propanals	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	3.17	5	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
inositol Inositol: An isomer of glucose that has traditionally been considered to be a B vitamin although it has an uncertain status as a vitamin and a deficiency syndrome has not been identified in man. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1379) Inositol phospholipids are important in signal transduction.. inositol : Any cyclohexane-1,2,3,4,5,6-hexol.. 1D-chiro-inositol : Belonging to the inositol family of compounds, D-chiro-inositol (DCI) is an isomer of glucose. It is an important secondary messenger in insulin signal transduction.. muco-inositol : An inositol that is cyclohexane-1,2,3,4,5,6-hexol having a (1R,2R,3r,4R,5S,6r)-configuration.	2.04	1	cyclitol; hexol
nickel Nickel: A trace element with the atomic symbol Ni, atomic number 28, and atomic weight 58.69. It is a cofactor of the enzyme UREASE.. nickel ion : A nickel atom having a net electric charge.. nickel atom : Chemical element (nickel group element atom) with atomic number 28.	2.84	3	metal allergen; nickel group element atom	epitope; micronutrient
phenol [no description available]	2.05	1	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
phenylacetaldehyde [no description available]	2.52	2	alpha-CH2-containing aldehyde; phenylacetaldehydes	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
propionic acid propionic acid : A short-chain saturated fatty acid comprising ethane attached to the carbon of a carboxy group.	2.05	1	saturated fatty acid; short-chain fatty acid	antifungal drug
pyridine azine : An organonitrogen compound of general structure RCH=N-N=CHR or RR'C=N-N=CRR'.	2.67	3	azaarene; mancude organic heteromonocyclic parent; monocyclic heteroarene; pyridines	environmental contaminant; NMR chemical shift reference compound
pyridoxal phosphate Pyridoxal Phosphate: This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).. pyridoxal 5'-phosphate : The monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal.	2.04	1	methylpyridines; monohydroxypyridine; pyridinecarbaldehyde; vitamin B6 phosphate	coenzyme; cofactor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae 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.	3.32	6	2-oxo monocarboxylic acid	cofactor; fundamental metabolite
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2.54	2	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
vanillin Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).	2.6	1	benzaldehydes; monomethoxybenzene; phenols	anti-inflammatory agent; anticonvulsant; antioxidant; flavouring agent; plant metabolite
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.25	1	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
2,2'-dipyridyl 2,2'-Dipyridyl: A reagent used for the determination of iron.. 2,2'-bipyridine : A bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'.	3.35	1	bipyridine	chelator; ferroptosis inhibitor
2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine: mutagen from fried ground beef; structure given in first source. PhIP : An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, amino, and phenyl groups, respectively. It is the most abundant of the mutagenic heterocyclic amines found in cooked meat and fish.	2.13	1	imidazopyridine; primary amino compound	carcinogenic agent; mutagen
baclofen [no description available]	2.13	1	amino acid zwitterion; gamma-amino acid; monocarboxylic acid; monochlorobenzenes; primary amino compound	central nervous system depressant; GABA agonist; muscle relaxant
ether Ether: A mobile, very volatile, highly flammable liquid used as an inhalation anesthetic and as a solvent for waxes, fats, oils, perfumes, alkaloids, and gums. It is mildly irritating to skin and mucous membranes.. ether : An organooxygen compound with formula ROR, where R is not hydrogen.. diethyl ether : An ether in which the oxygen atom is linked to two ethyl groups.	2.01	1	ether; volatile organic compound	inhalation anaesthetic; non-polar solvent; refrigerant
fluoxetine Fluoxetine: The first highly specific serotonin uptake inhibitor. It is used as an antidepressant and often has a more acceptable side-effects profile than traditional antidepressants.. fluoxetine : A racemate comprising equimolar amounts of (R)- and (S)-fluoxetine. A selective serotonin reuptake inhibitor (SSRI), it is used (generally as the hydrochloride salt) for the treatment of depression (and the depressive phase of bipolar disorder), bullimia nervosa, and obsessive-compulsive disorder.. N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine : An aromatic ether consisting of 4-trifluoromethylphenol in which the hydrogen of the phenolic hydroxy group is replaced by a 3-(methylamino)-1-phenylpropyl group.	2.07	1	(trifluoromethyl)benzenes; aromatic ether; secondary amino compound
gentamicin Gentamicins: A complex of closely related aminoglycosides obtained from MICROMONOSPORA purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit PROTEIN BIOSYNTHESIS.	2.31	1
glutaral Glutaral: One of the protein CROSS-LINKING REAGENTS that is used as a disinfectant for sterilization of heat-sensitive equipment and as a laboratory reagent, especially as a fixative.. glutaraldehyde : A dialdehyde comprised of pentane with aldehyde functions at C-1 and C-5.	2.01	1	dialdehyde	cross-linking reagent; disinfectant; fixative
guanidine Guanidine: A strong organic base existing primarily as guanidium ions at physiological pH. It is found in the urine as a normal product of protein metabolism. It is also used in laboratory research as a protein denaturant. (From Martindale, the Extra Pharmacopoeia, 30th ed and Merck Index, 12th ed) It is also used in the treatment of myasthenia and as a fluorescent probe in HPLC.. guanidine : An aminocarboxamidine, the parent compound of the guanidines.	2.45	2	carboxamidine; guanidines; one-carbon compound
2-propanol 2-Propanol: An isomer of 1-PROPANOL. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic.. propan-2-ol : A secondary alcohol that is propane in which one of the hydrogens attached to the central carbon is substituted by a hydroxy group.	2.08	1	secondary alcohol; secondary fatty alcohol	protic solvent
metformin Metformin: A biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. (From Martindale, The Extra Pharmacopoeia, 30th ed, p289). metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.	2.15	1	guanidines	environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic
tyramine [no description available]	2.41	1	monoamine molecular messenger; primary amino compound; tyramines	EC 3.1.1.8 (cholinesterase) inhibitor; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter
benzimidazole 1H-benzimidazole : The 1H-tautomer of benzimidazole.	2.08	1	benzimidazole; polycyclic heteroarene
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	2.05	1	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse 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.	2.73	3	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.	3.35	6	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
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	2.13	1	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
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.	2.02	1	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide.	2.1	1	pseudohalide anion	EC 1.9.3.1 (cytochrome c oxidase) inhibitor
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	2.11	1	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
uridine [no description available]	2.1	1	uridines	drug metabolite; fundamental metabolite; human metabolite
galactose galactopyranose : The pyranose form of galactose.	2.05	1	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.	2.51	2	amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine	EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
3-hydroxy-2-oxoindole 3-hydroxyindolin-2-one: structure in first source. 3-hydroxyindolin-2-one : An oxindole that is 1,3-dihydro-2H-indol-2-one substituted by a hydroxy group at position 3.	2.08	1	hydroxyindoles; oxindoles
desoxycorticosterone Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE	1.94	1	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
n-hexanal [no description available]	2	1	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human urinary metabolite
barbituric acid barbituric acid: RN given refers to parent cpd; structure from Merck Index, 9th ed, #966. barbituric acid : A barbiturate, the structure of which is that of perhydropyrimidine substituted at C-2, -4 and -6 by oxo groups. Barbituric acid is the parent compound of barbiturate drugs, although it is not itself pharmacologically active.	2.08	1	barbiturates	allergen; xenobiotic
bromoacetate [no description available]	2.08	1	carboxylic acid; organohalogen compound
ampicillin Ampicillin: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.. ampicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-phenylacetamido group.	2.31	1	beta-lactam antibiotic; penicillin allergen; penicillin	antibacterial drug
mannitol [no description available]	2.03	1	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
phenacyl bromide phenacyl bromide: structure. phenacyl bromide : An alpha-bromoketone that is acetophenone substituted by a bromo group at position 2.	2.1	1	acetophenones; alpha-bromoketone	metabolite
histidine Histidine: An essential amino acid that is required for the production of HISTAMINE.. L-histidine : The L-enantiomer of the amino acid histidine.. histidine : An alpha-amino acid that is propanoic acid bearing an amino substituent at position 2 and a 1H-imidazol-4-yl group at position 3.	3.44	7	amino acid zwitterion; histidine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	2.02	1	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
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.	2.02	1	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.	3.15	5	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
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	2.77	3	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; 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.	2.07	1	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
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	2.47	2	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
ethane Ethane: A two carbon alkane with the formula H3C-CH3.. ethane : An alkane comprising of two carbon atoms.	2.11	1	alkane; gas molecular entity	plant metabolite; refrigerant
ethylene Plastipore: high density polyethylene sponge biocompatible material; used as posts in dental bridges	3.59	2	alkene; gas molecular entity	plant hormone; refrigerant
acetylene [no description available]	2.13	1	alkyne; gas molecular entity; terminal acetylenic compound
methylamine methyl group : An alkyl group that is the univalent group derived from methane by removal of a hydrogen atom.	2.02	1	methylamines; one-carbon compound; primary aliphatic amine	mouse metabolite
boranes Boranes: The collective name for the boron hydrides, which are analogous to the alkanes and silanes. Numerous boranes are known. Some have high calorific values and are used in high-energy fuels. (From Grant & Hackh's Chemical Dictionary, 5th ed). borane : The simplest borane, consisting of a single boron atom carrying three hydrogens.. boranes : The molecular hydrides of boron.	3.32	6	boranes; mononuclear parent hydride
methylene chloride Methylene Chloride: A chlorinated hydrocarbon that has been used as an inhalation anesthetic and acts as a narcotic in high concentrations. Its primary use is as a solvent in manufacturing and food technology.. dichloromethane : A member of the class of chloromethanes that is methane in which two of the hydrogens have been replaced by chlorine. A dense, non-flammible colourless liquid at room temperature (b.p. 40degreeC, d = 1.33) which is immiscible with water, it is widely used as a solvent, a paint stripper, and for the removal of caffeine from coffee and tea.	2.11	1	chloromethanes; volatile organic compound	carcinogenic agent; polar aprotic solvent; refrigerant
cyclopropane cyclopropane : A cycloalkane composed of three carbon atoms to form a ring.	2.44	2	cycloalkane; cyclopropanes	inhalation anaesthetic
ethylene oxide Ethylene Oxide: A colorless and flammable gas at room temperature and pressure. Ethylene oxide is a bactericidal, fungicidal, and sporicidal disinfectant. It is effective against most micro-organisms, including viruses. It is used as a fumigant for foodstuffs and textiles and as an agent for the gaseous sterilization of heat-labile pharmaceutical and surgical materials. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p794). oxirane : A saturated organic heteromonocyclic parent that is a three-membered heterocycle of two carbon atoms and one oxygen atom.	2.31	1	gas molecular entity; oxacycle; saturated organic heteromonocyclic parent	allergen; mouse metabolite; mutagen
nitromethane nitromethane: structure. nitromethane : A primary nitroalkane that is methane in which one of the hydrogens is replace by a nitro group. A polar solvent (b.p. 101 degreeC), it is an important starting material in organic synthesis. It is also used as a fuel for rockets and radio-controlled models.	2.48	2	primary nitroalkane; volatile organic compound	EC 4.3.1.3 (histidine ammonia-lyase) inhibitor; explosive; NMR chemical shift reference compound; polar aprotic solvent
tert-butylhydroperoxide tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.	2.08	1	alkyl hydroperoxide	antibacterial agent; oxidising agent
trifluoroacetic acid Trifluoroacetic Acid: A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.. trifluoroacetic acid : A monocarboxylic acid that is the trifluoro derivative of acetic acid.	2.45	2	fluoroalkanoic acid	human xenobiotic metabolite; NMR chemical shift reference compound; reagent
isobutyraldehyde isobutyraldehyde : A member of the class of propanals that is propanal substituted by a methyl group at position 2.	2.55	2	2-methyl-branched fatty aldehyde; propanals	Saccharomyces cerevisiae metabolite
methylethyl ketone methylethyl ketone: solvent; colorless synthetic resins, smokeless powders; may be irritating to eyes, mucous membranes; may be toxic in high concentrations; structure. butanone : Any ketone that is butane substituted by an oxo group at unspecified position.. butan-2-one : A dialkyl ketone that is a four-carbon ketone carrying a single keto- group at position C-2.	2	1	butanone; dialkyl ketone; methyl ketone; volatile organic compound	bacterial metabolite; polar aprotic solvent
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	2.44	2	alpha,beta-unsaturated monocarboxylic acid	metabolite
pantothenic acid Pantothenic Acid: A butyryl-beta-alanine that can also be viewed as pantoic acid complexed with BETA ALANINE. It is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.. pantothenic acid : A member of the class of pantothenic acids that is an amide formed from pantoic acid and beta-alanine.. vitamin B5 : Any member of a group of vitamers that belong to the chemical structural class called pantothenic acids that exhibit biological activity against vitamin B5 deficiency. Deficiency of vitamin B5 is rare due to its widespread distribution in whole grain cereals, legumes and meat. Symptoms associated with vitamin B5 deficiency are difficult to asses since they are subtle and resemble those of other B vitamin deficiencies. The vitamers include (R)-pantothenic acid and its ionized and salt forms.. (R)-pantothenate : A pantothenate that is the conjugate base of (R)-pantothenic acid, obtained by deprotonation of the carboxy group.. (R)-pantothenic acid : A pantothenic acid having R-configuration.	2.11	1	pantothenic acid; vitamin B5	antidote to curare poisoning; geroprotector; human blood serum metabolite
salicylaldehyde o-hydroxybenzaldehyde: structure in first source	2.06	1	hydroxybenzaldehyde	nematicide; plant metabolite
decalin decalin: RN given refers to cpd without isomeric designation; don't confuse with decaline which has a nitrogen at the juncture of the two rings;. trans-decalin : The trans-stereoisomer of decalin.. decalin : An ortho-fused bicyclic hydrocarbon that is the decahydro- derivative of naphthalene.	3.11	4	ortho-fused bicyclic hydrocarbon	solvent
isatin tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal;	3.36	6	indoledione	EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
xanthenes Xanthenes: Compounds with three aromatic rings in linear arrangement with an OXYGEN in the center ring.	2.03	1	xanthene
indene indene: structure in first source. 1H-indene : An ortho-fused bicyclic arene comprising of benzene and cyclopentene rings.	2.41	1	indene; ortho-fused bicyclic arene
4-butyrolactone 4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.	3.78	10	butan-4-olide	metabolite; neurotoxin
furaldehyde Furaldehyde: A heterocyclic compound consisting of a furan where the hydrogen at position 2 is substituted by a formyl group.. furfural : An aldehyde that is furan with the hydrogen at position 2 substituted by a formyl group.	2.06	1	aldehyde; furans	Maillard reaction product; metabolite
acetophenone acetophenone : A methyl ketone that is acetone in which one of the methyl groups has been replaced by a phenyl group.	2.46	2	acetophenones	animal metabolite; photosensitizing agent; xenobiotic
nitrobenzene nitrobenzene : A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.	2.04	1	nitroarene; nitrobenzenes
carvone carvone: an oxidized derivative of limonene; RN given refers to cpd without isomeric designation; L-carvone has spearmint flavor, D-carvone has dill/caraway flavor. carvone : A p-menthane monoterpenoid that consists of cyclohex-2-enone having methyl and isopropenyl substituents at positions 2 and 5, respectively.	2.58	2	botanical anti-fungal agent; carvones	allergen
butane butane : A straight chain alkane composed of 4 carbon atoms.	2.02	1	alkane; gas molecular entity	food propellant; refrigerant
1,3-butadiene buta-1,3-diene : A butadiene with unsaturation at positions 1 and 3.	2.53	2	butadiene	carcinogenic agent; mutagen
acrolein [no description available]	2.04	1	enal	herbicide; human xenobiotic metabolite; toxin
allyl alcohol allyl alcohol: structure. allylic alcohol : An alcohol where the hydroxy group is attached to a saturated carbon atom adjacent to a double bond (R groups may be H, organyl, etc.).. allyl alcohol : A propenol in which the C=C bond connects C-2 and C-3. It is has been found in garlic (Allium sativum). Formerly used as a herbicide for the control of various grass and weed seeds.	2.75	3	primary allylic alcohol; propenol	antibacterial agent; fungicide; herbicide; insecticide; plant metabolite
glyoxal [no description available]	2.49	2	dialdehyde	agrochemical; allergen; pesticide; plant growth regulator
sarin Sarin: An organophosphorus ester compound that produces potent and irreversible inhibition of cholinesterase. It is toxic to the nervous system and is a chemical warfare agent.. isopropyl methylphosphonofluoridate : A phosphinic ester that is the isopropyl ester of methylphosphonofluoridic acid.. sarin : A racemate composed of equal amounts of (R)- and (S)-sarin. A potent and irreversible inhibitor of acetylcholinesterase that is toxic to the nervous system and is employed as a chemical warfare agent.	2.04	1	fluorine molecular entity; phosphinic ester
2-methylpentane Hexanes: Six-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Various polyneuropathies are caused by hexane poisoning.	2.1	1	alkane
diisopropylamine diisopropylamine: structure given in first source	2.13	1
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	2.1	1	cyclohexanols; secondary alcohol	solvent
cyclohexanone [no description available]	3.87	11	cyclohexanones	human xenobiotic metabolite
pentane Pentanes: Five-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives.. pentane : A straight chain alkane consisting of 5 carbon atoms.	2.02	1	alkane; volatile organic compound	non-polar solvent; refrigerant
dicyanmethane malononitrile : A dinitrile that is methane substituted by two cyano groups.	3.41	1	aliphatic nitrile; dinitrile
diethylamine [no description available]	2.08	1	secondary aliphatic amine
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	3.48	7	pyrrole; secondary amine
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	2.76	3	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
thiophenes Thiophenes: A monocyclic heteroarene furan in which the oxygen atom is replaced by a sulfur.. thiophenes : Compounds containing at least one thiophene ring.	2.07	1	mancude organic heteromonocyclic parent; monocyclic heteroarene; thiophenes; volatile organic compound	non-polar solvent
pentanal pentanal : A saturated fatty aldehyde composed from five carbons in a straight chain.	2.15	1	saturated fatty aldehyde	plant metabolite
cyclohexane Cyclohexane: C6H12. cyclohexane : An alicyclic hydrocarbon comprising a ring of six carbon atoms; the cyclic form of hexane, used as a raw material in the manufacture of nylon.	2.06	1	cycloalkane; volatile organic compound	non-polar solvent
piperidine [no description available]	2.13	1	azacycloalkane; piperidines; saturated organic heteromonocyclic parent; secondary amine	base; catalyst; human metabolite; non-polar solvent; plant metabolite; protic solvent; reagent
acetol hydroxyacetone : A propanone that is acetone in which one of the methyl hydrogens is replaced by a hydroxy group.	4.08	4	methyl ketone; primary alcohol; primary alpha-hydroxy ketone; propanones	Escherichia coli metabolite; human metabolite; mouse metabolite
piperonal piperonal: has been used as a pediculicide; structure. piperonal : An arenecarbaldehyde that is 1,3-benzodioxole substituted by a formyl substituent at position 5. It has been isolated from Piper nigrum.	2	1	arenecarbaldehyde; benzodioxoles	fragrance; insect repellent; plant metabolite
cyclopentanone [no description available]	3.01	4	cyclopentanones	Maillard reaction product
triethylamine [no description available]	2.45	2	tertiary amine
syringaldehyde syringaldehyde: isolated from nonfermented fiber fractions of oat hulls and cottonseed hulls. syringaldehyde : A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity.	2.6	1	dimethoxybenzene; hydroxybenzaldehyde	hypoglycemic agent; plant metabolite
2-naphthol 2-naphthol: RN given refers to parent cpd. 2-naphthol : A naphthol carrying a hydroxy group at position 2.. naphthols : Any hydroxynaphthalene derivative that has a single hydroxy substituent.	3.31	6	naphthol	antinematodal drug; genotoxin; human urinary metabolite; human xenobiotic metabolite; mouse metabolite; radical scavenger
mesityl oxide mesityl oxide: solvent for extraction of nitrocellulose, many resins, & tellurium; structure	2.13	1	olefinic compound
2-hydroxypyridine hydroxypyridine : Any member of the class of pyridines with at least one hydroxy substituent.. pyridin-2-ol : A monohydroxypyridine that is pyridine substituted by a hydroxy group at position 2.	2.07	1	monohydroxypyridine	plant metabolite
pregnenolone [no description available]	2.06	1	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
formaldehydesulfoxylate formaldehydesulfoxylate: antidote for mercury poisoning; RN given refers to parent cpd; structure	2.41	1
perylene Perylene: A 20-carbon dibenz(de,kl)anthracene that can be viewed as a naphthalene fused to a phenalene or as dinaphthalene. It is used as fluorescent lipid probe in the cytochemistry of membranes and is a polycyclic hydrocarbon pollutant in soil and water. Derivatives may be carcinogenic.. perylene : An ortho- and peri-fused polycyclic arene comprising of five benzene rings that is anthracene in which the d,e and k,l sides are fused to benzene rings.	2.05	1	ortho- and peri-fused polycyclic arene; perylenes
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.5	2	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
benzofuran benzofuran: RN & structure given in first source. 1-benzofuran : A benzofuran consisting of fused benzene and furan rings. It is the parent compound of the class of 1-benzofurans.	2.08	1	1-benzofurans; benzofuran
indolizine [no description available]	2.03	1	indolizines; mancude organic heterobicyclic parent
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.48	2	adamantanes; polycyclic alkane
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	3.79	10	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.1	1	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	3.55	8	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
thiazoles [no description available]	2.44	2	1,3-thiazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
pyrimidine pyrimidine : The parent compound of the pyrimidines; a diazine having the two nitrogens at the 1- and 3-positions.	2.08	1	diazine; pyrimidines	Daphnia magna metabolite
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	2.01	1	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
cyanoacetic acid cyanoacetic acid: RN given refers to parent cpd; structure. cyanoacetic acid : A monocarboxylic acid that consists of acetic acid bearing a cyano substituent.	2.13	1	monocarboxylic acid
propadiene [no description available]	2.74	3	allenes
ketene ketene: structure. ketene : Carbonyl compounds where the C=O bond is conjugated to an alkylidene group.	3.31	6	ketene
propiolic acid propiolic acid: RN given refers to parent cpd; structure. propynoic acid : A terminal acetylenic compound that is a 3-carbon, straight-chain, monounsaturated fatty acid having one acetylenic bond.	2.03	1	acetylenic fatty acid; alpha,beta-unsaturated monocarboxylic acid; monounsaturated fatty acid; short-chain fatty acid; terminal acetylenic compound	xenobiotic metabolite
plumbagin plumbagin: a superoxide anion generator. plumbagin : A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively.	2.6	1	hydroxy-1,4-naphthoquinone; phenols	anticoagulant; antineoplastic agent; immunological adjuvant; metabolite
hydrindane hydrindane: structure in first source. hydrindane : An ortho-fused bicyclic hydrocarbon comprising of a cyclohexane ring fused onto a cyclopentane ring.	2.31	1	ortho-fused bicyclic hydrocarbon
indan indan: structure in first source. indane : An ortho-fused bicyclic hydrocarbon consisting of a benzene ring fused to a cyclopentane ring; a high-boiling (176 (o)C) colourless liquid.	2.49	2	indanes; ortho-fused bicyclic hydrocarbon
butenolide butenolide: inhibits experimental allergic encephalomyelitis in rats. butenolide : A gamma-lactone that consists of a 2-furanone skeleton and its substituted derivatives.	3.34	6	butenolide
thiazolidines Thiazolidines: Reduced (protonated) form of THIAZOLES. They can be oxidized to THIAZOLIDINEDIONES.	3.76	10	thiazolidine
1,1-dimethoxyethane 1,1-dimethoxyethane : An acetal that is dimethoxymethane substituted by a methyl group at position 1.	2.04	1	acetal; diether	flavouring agent; plant metabolite
2-methylfuran 2-methylfuran : A member of the class of furans that is furan in which the hydrogen at position 2 is replaced by a methyl group.	2.13	1	furans; volatile organic compound	flavouring agent; fuel; hepatotoxic agent; human urinary metabolite; plant metabolite
phenylacetylene phenylacetylene: can polymerize into DENDRIMERS	2.13	1	benzenes
muscone muscone: structure in first source	2.03	1
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.	2.15	1	dialdehyde	biomarker
isoserine isoserine: RN given refers to cpd without isomeric designation	2.05	1
1,3-indandione 1,3-indandione : A member of the class of indanones that is indane in which the hydrogens at positions 2 and 4 have been replaced by oxo groups.	2.11	1	aromatic ketone; beta-diketone; indanones
acetylcysteine N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.	2.05	1	acetylcysteine; L-cysteine derivative; N-acetyl-L-amino acid	antidote to paracetamol poisoning; antiinfective agent; antioxidant; antiviral drug; ferroptosis inhibitor; geroprotector; human metabolite; mucolytic; radical scavenger; vulnerary
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.	3.82	3	cyclic ketone; erythromycin
hempa Hempa: A chemosterilant agent that is anticipated to be a carcinogen.	2.05	1	phosphoramide	insect sterilant; mutagen
4-nitrophenyl acetate [no description available]	2.04	1	C-nitro compound; phenyl acetates
cyclopentenone 2-cyclopenten-1-one : An enone that is cyclopentanone having a C=C double bond at position 2.	2.8	3	alicyclic ketone; enone	Hsp70 inducer
2-cyclohexen-1-one 2-cyclohexen-1-one: RN given refers to unlabeled cpd with specified locant for double bond. cyclohexenone : The parent compound of the cyclohexenones, composed of cyclohexanone having one double bond in the ring.. cyclohex-2-enone : A cyclohexenone having its C=C double bond at the 2-position.	2.11	1	cyclohexenone
hexamethylsilazane hexamethylsilazane: RN given refers to parent cpd	2.05	1	N-silyl compound	chromatographic reagent
pyridine-2-carboxaldehyde pyridine-2-carboxaldehyde: structure in first source. 2-formylpyridine : A pyridinecarbaldehyde that is pyridine in which the hydrogen at position 2 is replaced by a formyl group.	2.08	1	pyridinecarbaldehyde
durapatite Durapatite: The mineral component of bones and teeth; it has been used therapeutically as a prosthetic aid and in the prevention and treatment of osteoporosis.. hydroxylapatite : A phosphate mineral with the formula Ca5(PO4)3(OH).	2.08	1
potassium hydroxide potassium hydroxide: RN given refers to cpd with MF of K-OH	2.07	1	alkali metal hydroxide
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	1.99	1	alkali metal hydroxide
tert-butyl acrylate tert-butyl acrylate: structure in first source	2.06	1
tetrabutylammonium tetrabutylammonium: lipophilic probe; RN given refers to parent cpd	2.25	1	quaternary ammonium ion
mannose mannopyranose : The pyranose form of mannose.	2.06	1	D-aldohexose; D-mannose; mannopyranose	metabolite
carbonates Carbonates: Salts or ions of the theoretical carbonic acid, containing the radical CO2(3-). Carbonates are readily decomposed by acids. The carbonates of the alkali metals are water-soluble; all others are insoluble. (From Grant & Hackh's Chemical Dictionary, 5th ed). carbonates : Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.	2.05	1	carbon oxoanion
fructosamine Fructosamine: An amino sugar formed when glucose non-enzymatically reacts with the N-terminal amino group of proteins. The fructose moiety is derived from glucose by the classical Amadori rearrangement.	2.15	1
limonene Limonene: A naturally-occurring class of MONOTERPENES which occur as a clear colorless liquid at room temperature. Limonene is the major component in the oil of oranges which has many uses, including as flavor and fragrance. It is recognized as safe in food by the Food and Drug Administration (FDA).. limonene : A monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively.	2.07	1	cycloalkene; p-menthadiene	human metabolite
iridium Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.	2.49	2	cobalt group element atom; platinum group metal atom
manganese Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.	2.05	1	elemental manganese; manganese group element atom	Escherichia coli metabolite; micronutrient
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	3.67	9	metal allergen; nickel group element atom; platinum group metal atom
platinum Platinum: A heavy, soft, whitish metal, resembling tin, with atomic number 78, atomic weight 195.084, symbol Pt. It is used in manufacturing equipment for laboratory and industrial use. It occurs as a black powder (platinum black) and as a spongy substance (spongy platinum) and may have been known in Pliny's time as alutiae.	2.31	1	elemental platinum; nickel group element atom; platinum group metal atom
rhenium Rhenium: A metal, atomic number 75, atomic weight 186.207, symbol Re.	2.05	1	manganese group element atom
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	4.04	13	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	3.06	4	iron group element atom; platinum group metal atom
samarium Samarium: An element of the rare earth family of metals. It has the atomic symbol Sm, atomic number 62, and atomic weight 150.36. The oxide is used in the control rods of some nuclear reactors.	2.11	1	f-block element atom; lanthanoid atom
scandium Scandium: An element of the rare earth family of metals. It has the atomic symbol Sc, atomic number 21, and atomic weight 45.	2.01	1	d-block element atom; rare earth metal atom; scandium group element atom
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	2.97	4	copper group element atom; elemental silver	Escherichia coli metabolite
titanium Titanium: A dark-gray, metallic element of widespread distribution but occurring in small amounts with atomic number, 22, atomic weight, 47.867 and symbol, Ti; specific gravity, 4.5; used for fixation of fractures.	3.44	7	titanium group element atom
tungsten Tungsten: A metallic element with the atomic symbol W, atomic number 74, and atomic weight 183.85. It is used in many manufacturing applications, including increasing the hardness, toughness, and tensile strength of steel; manufacture of filaments for incandescent light bulbs; and in contact points for automotive and electrical apparatus.	2.06	1	chromium group element atom	micronutrient
europium Europium: An element of the rare earth family of metals. It has the atomic symbol Eu, atomic number 63, and atomic weight 152. Europium is used in the form of its salts as coatings for cathode ray tubes and in the form of its organic derivatives as shift reagents in NMR spectroscopy.	2.1	1	f-block element atom; lanthanoid atom
gold Gold: A yellow metallic element with the atomic symbol Au, atomic number 79, and atomic weight 197. It is used in jewelry, goldplating of other metals, as currency, and in dental restoration. Many of its clinical applications, such as ANTIRHEUMATIC AGENTS, are in the form of its salts.	3.34	6	copper group element atom; elemental gold
vanadium Vanadium: A metallic element with the atomic symbol V, atomic number 23, and atomic weight 50.94. It is used in the manufacture of vanadium steel. Prolonged exposure can lead to chronic intoxication caused by absorption usually via the lungs.	2.08	1	elemental vanadium; vanadium group element atom	micronutrient
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	2.47	2	titanium group element atom
acetylglucosamine Acetylglucosamine: The N-acetyl derivative of glucosamine.. N-acetyl-beta-D-glucosamine : An N-acetyl-D-glucosamine having beta-configuration at the anomeric centre.	2.6	1	N-acetyl-D-glucosamine	epitope
titanium tetrachloride titanium tetrachloride: RN given refers to TiCl4	2.01	1
camptothecin NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source	2.03	1	delta-lactone; pyranoindolizinoquinoline; quinoline alkaloid; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor; genotoxin; plant metabolite
phosphine phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.	3.37	6	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	2.43	2	dihydrogen
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	2.02	1	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	2.73	3
trichlorosilane [no description available]	2.05	1
silicon tetrachloride [no description available]	2.78	3
rhamnose [no description available]	2.07	1	L-rhamnose
tiletamine hydrochloride Cyclohexanones: Cyclohexane ring substituted by one or more ketones in any position.. cyclohexanones : Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.	4.21	16
fluorides [no description available]	2.81	3	halide anion; monoatomic fluorine
1-deoxynojirimycin 1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.	2.05	1	2-(hydroxymethyl)piperidine-3,4,5-triol; piperidine alkaloid	anti-HIV agent; anti-obesity agent; bacterial metabolite; EC 3.2.1.20 (alpha-glucosidase) inhibitor; hepatoprotective agent; hypoglycemic agent; plant metabolite
iodine [no description available]	2.75	3	halide anion; monoatomic iodine	human 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.	4.04	14	benzenes; phenyl acetates
diacetone alcohol diacetone alcohol: skin irritant & catalyst for the resin used in fiberglass manufacture. diacetone alcohol : A beta-hydroxy ketone formed by hydroxylation of 4-methylpentan-2-one at the 4-position. It has been isolated from Achnatherum robustum.	2.02	1	beta-hydroxy ketone	plant metabolite
pyrrolidine [no description available]	2.79	3	azacycloalkane; pyrrolidines; saturated organic heteromonocyclic parent
1,4-dioxane 1,4-dioxane: dehydrating agent; polar solvent miscible both with water & most organic solvents. dioxane : Any member of the class of dioxanes that is a cyclohexane in which two carbon atoms are replaced by oxygen atoms.. 1,4-dioxane : A dioxane with oxygen atoms at positions 1 and 4.	2.07	1	dioxane; volatile organic compound	carcinogenic agent; metabolite; NMR chemical shift reference compound; non-polar solvent
alkenes [no description available]	4.21	16
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.	2.02	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
azides Azides: Organic or inorganic compounds that contain the -N3 group.. azide : Any nitrogen molecular entity containing the group -N3.	3.03	4	pseudohalide anion	mitochondrial respiratory-chain inhibitor
atorvastatin [no description available]	2.51	2	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
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.	2.05	1	pentenoic acid
trifluoromethanesulfonic acid trifluoromethanesulfonic acid: deblocking reagent for peptide synthesis; RN given refers to parent cpd. triflic acid : A one-carbon compound that is methanesulfonic acid in which the hydrogens attached to the methyl carbon have been replaced by fluorines.	2.45	2	one-carbon compound; perfluoroalkanesulfonic acid
isothiocyanic acid [no description available]	2.04	1	hydracid; one-carbon compound
efavirenz efavirenz: HIV-1 reverse transcriptase inhibitor. efavirenz : 1,4-Dihydro-2H-3,1-benzoxazin-2-one substituted at the 4 position by cyclopropylethynyl and trifluoromethyl groups (S configuration) and at the 6 position by chlorine. A non-nucleoside reverse transcriptase inhibitor with activity against HIV, it is used with other antiretrovirals for combination therapy of HIV infection.	2.1	1	acetylenic compound; benzoxazine; cyclopropanes; organochlorine compound; organofluorine compound	antiviral drug; HIV-1 reverse transcriptase inhibitor
cyclen cyclen: macrocyclic polyamine metal-complexing agent. 1,4,7,10-tetraazacyclododecane : An azacycloalkane that is cyclododecane in which the carbon atoms at positions 1, 4, 7 and 10 are replaced by nitrogen atoms.	2.08	1	azacycloalkane; crown amine; saturated organic heteromonocyclic parent
trimethylsilyl trifluoromethanesulfonate trimethylsilyl trifluoromethanesulfonate: deprotecting cpd for peptides	2.04	1
trifluoroacetaldehyde [no description available]	2.11	1
naphthalimides Naphthalimides: Compounds with three fused rings that appear like a naphthalene fused to piperidone or like a benz(de)isoquinoline-1,3-dione (not to be confused with BENZYLISOQUINOLINES which have a methyl separating the naphthyl from the benzyl rings). Members are CYTOTOXINS.	2.1	1
benzeneboronic acid [no description available]	2.08	1	boronic acids
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.	2.82	3	1,2,3-triazole
3-fluoropyruvate 3-fluoropyruvate: a substrate for E coli pyruvate dehydrogenase; structure; RN given refers to parent cpd. 3-fluoropyruvic acid : A pyruvic acid derivative having a 3-fluoro substituent.. 3-fluoropyruvate : The anion of 3-fluoropyruvic acid.	2.13	1	2-oxo monocarboxylic acid; organofluorine compound
isocoumarins Isocoumarins: Compounds that differ from COUMARINS in having the positions of the ring and ketone oxygens reversed so the keto oxygen is at the 1-position of the molecule.. isocoumarin : The simplest member of the class of isocoumarins that is 1H-isochromene which is substituted by an oxo group at position 1.	2.52	2	isocoumarins
fructose-6-phosphate fructose-6-phosphate: RN given refers to parent cpd with unspecified isomeric designation. fructose 6-phosphate : A ketohexose monophosphate consisting of fructose having a phosphate group located at the 6-position.	2.1	1	D-fructose 6-phosphate
tryptanthrine tryptanthrine: minor constituent of traditional Chinese medicine qing dai	2.5	2	alkaloid antibiotic; organic heterotetracyclic compound; organonitrogen heterocyclic compound
oxazolidin-2-one Oxazolidinones: Derivatives of oxazolidin-2-one. They represent an important class of synthetic antibiotic agents.. oxazolidin-2-one : An oxazolidinone that is 1,3-oxazolidine with an oxo substituent at position 2.. oxazolidinone : An oxazolidine containing one or more oxo groups.	3.21	5	carbamate ester; oxazolidinone	metabolite
tetrabutylphosphonium tetrabutylphosphonium: RN given refers to Br	2.1	1
t 1982 1,3,4,6,7,8-hexahydro-2H-pyrimido(1,2-a)pyrimidine: structure in first source	2.06	1	pyrimidines
nicotine (S)-nicotine : A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.	2.41	1	3-(1-methylpyrrolidin-2-yl)pyridine	anxiolytic drug; biomarker; immunomodulator; mitogen; neurotoxin; nicotinic acetylcholine receptor agonist; peripheral nervous system drug; phytogenic insecticide; plant metabolite; psychotropic drug; teratogenic agent; xenobiotic
lupinine lupinine: RN given refers to parent cpd(1R-trans)-isomer; structure	2.06	1	quinolizidine alkaloid
homocysteine Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.	2.11	1	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
16-dehydropregnenolone 16,17-didehydropregnenolone : A 3beta-hydroxy-Delta(5)-steroid that is pregnenolone with a double bond between positions 16 and 17.	2.06	1	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; enone
erythrose D-erythrose : The D-enantiomer of erythrose.	2.02	1	erythrose	plant metabolite
viridin viridin: bacteriocins of alpha-hemolytic streptococcal isolates; RN given refers to (1S-(1alpha,2alpha,11balpha))-isomer	2.07	1
allenolic acid allenolic acid: structure in first source	2.42	2	naphthols
galgravin galgravin: an anti-PAF constituent from the stems of Piper futokadsura, the Chinese drug haifengteng; structures of the isomers galgravin, galbelgin (10569-12-7) and veraguensin (19950-55-1) given in first source; RN given refers to galgravin, the (2alpha,3beta,4beta,5alpha)-isomer. galgravin : A member of the class of aryltetrahydrofurans carrying two 3,4-dimethoxyphenyl substituents at positions 2 and 5 as well as two methyl groups at positions 3 and 4.	2.05	1	aryltetrahydrofuran; dimethoxybenzene; lignan; ring assembly	bone density conservation agent; neuroprotective agent; plant metabolite; platelet aggregation inhibitor
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.	2.78	3	cobalt group element atom; metal allergen	micronutrient
bromoacetaldehyde bromoacetaldehyde: RN given refers to unlabeled cpd	2.03	1	organobromine compound
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.07	1
prolinamide prolinamide: RN given refers to cpd without isomeric designation. L-prolinamide : The carboxamide derivative of L-proline.	3.58	8	amino acid amide; L-proline derivative; pyrrolidinecarboxamide
2,3-bis(3'-hydroxybenzyl)butyrolactone 2,3-bis(3'-hydroxybenzyl)butyrolactone: lignan isolated from urine of humans & other mammals; RN given refers to cpd without isomeric designation; structure given in second source	2.05	1	lignan
6-deoxyerythronolide b 6-deoxyerythronolide B: Streptomyces erythreus metabolite; presumed intermediate in biosynthesis of erythromycins; structure given in first source	2.01	1	erythronolide
glucosylgalactosylhydroxylysine glucosylgalactosylhydroxylysine: from sponge & sea anemone collagen	2.21	1
carbene carbene: electrically neutral species H2C: and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons; carbene is the name of the parent hydride :CH2 ; hence, the name dichlorocarbene for :CCl2. However, names for acyclic and cyclic hydrocarbons containing one or more divalent carbon atoms are derived from the name of the corresponding all-4-hydrocarbon using the suffix -ylidene; methylene carbene also available. carbene : The electrically neutral species H2C(2.) and its derivatives, in which the carbon is covalently bonded to two univalent groups of any kind or a divalent group and bears two nonbonding electrons, which may be spin-paired (singlet state) or spin-non-paired (triplet state).	2.74	3	carbene; methanediyl
phosphoramide phosphoramide: RN given refers to triamide. phosphoramide : A compound in which one or more of the OH groups of phosphoric acid have been replaced with an amino or substituted amino group. The term is commonly confined to the phosphoric triamides, P(=O)(NR2)3, since replacement of one or two OH groups produces phosphoramidic acids: P(=O)(OH)(NR2)2 , P(=O)(OH)2(NR2).	2.05	1
sauristolactam sauristolactam: lactam of 10-aminomethyl-3-hydroxy-4-methoxyphenanthrene-1-carboxylic acid isolated from Saururus cernuus; structure given in first source	2.04	1
n-(3-phenyl-n-propyl)-1-phenyl-2-aminopropane N-(3-phenyl-n-propyl)-1-phenyl-2-aminopropane: sigma receptor ligand	2.41	1
l 733060 3-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-2-phenylpiperidine: RN given refers to (2S-cis)-isomer; L-733,061 is pharmacologically inactive; structure in first source	2.07	1	piperidines
5-deoxyribose 1-phosphate 5-deoxyribose 1-phosphate: structure given in first source	2.17	1
dithiane dithiane: structure in first source	2.13	1	dithiane
beta-lactams 2-azetidinone: structure in first source. azetidin-2-one : An unsubstituted beta-lactam compound.. beta-lactam : A lactam in which the amide bond is contained within a four-membered ring, which includes the amide nitrogen and the carbonyl carbon.	2.45	2	beta-lactam antibiotic allergen; beta-lactam
cyclohexadienone cyclohexadienone: structure in first source	2.06	1
sperm motility inhibitor 2 [no description available]	2.11	1
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	6.67	66	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
ribulose ribulose: 5-carbon keto sugar; minor descriptor (75-85); on-line & Index Medicus search PENTOSES (75-85); RN given refers to (erythro)-isomer	2.15	1	ribulose	Escherichia coli metabolite; human metabolite
chiriquitoxin chiriquitoxin: natural analog of tetrodotoxin isolated from Central American frog Atelopus chiriquensis	2.1	1
erythrulose [no description available]	2.02	1	ketotetrose; primary alpha-hydroxy ketone; secondary alpha-hydroxy ketone
scytolone scytolone: intermediate in melanin biosynthesis by Verticillium dahliae. scytalone : A cyclic ketone that is 3,4-dihydronaphthalen-1(2H)-one substituted by hydroxy groups at positions 3, 6, and 8.	2.04	1
aristololactam bii aristololactam BII: isolated from Saururus cernuus; structure given in first source	2.04	1
myristamidopropyl dimethylamine myristamidopropyl dimethylamine: antimicrobial solution	2.6	1
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.	2.25	1	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
valiolamine valiolamine: isolated from Streptomyces hygroscopicus; RN from CA Index; RN not in Chemline 2/85	2.04	1
lignin Lignin: The most abundant natural aromatic organic polymer found in all vascular plants. Lignin together with cellulose and hemicellulose are the major cell wall components of the fibers of all wood and grass species. Lignin is composed of coniferyl, p-coumaryl, and sinapyl alcohols in varying ratios in different plant species. (From Merck Index, 11th ed). lignin : A polyphenylpropanoid derived from three monolignol monomers: trans-p-coumaryl alcohol, coniferol and trans-sinapyl alcohol. There is extensive cross-linking and no defined primary structure.	2.83	3
organophosphonates hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.	3.56	8	divalent inorganic anion; phosphite ion
mycosamine mycosamine: structure	2.07	1	deoxymannose derivative; mannosamine
valienamine valienamine: intermediate formed by microbial degradation of validamycins; structure given in first source	2.05	1
diphenylprolinol diphenylprolinol: a psychoactive drug; structure in first source	2.31	1
diflomotecan diflomotecan: a fluorinated E-ring modified camptothecin; structure in first source. diflomotecan : An organic heteropentacyclic compound that is (5R)-8-[(6,7-difluoroquinolin-3-yl)methyl]-5-ethyl-5-hydroxy-1,4,5,8-tetrahydrooxepino[3,4-c]pyridine-3,9-dione in which position 7 of the oxepinopyridine moiety is joined to position 3 of the difluoroquinoine ring by a single bond. An E-ring modified camptothecin analogue that has greater lactone stability in plasma compared with other topoisomerase I inhibitors.	2.03	1	epsilon-lactone; organic heteropentacyclic compound; organofluorine compound; organonitrogen heterocyclic compound; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor
5-hydroxymethylfurfural 5-hydroxymethylfurfural: has antisickling activity; HMF is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo. 5-hydroxymethylfurfural : A member of the class of furans that is furan which is substituted at positions 2 and 5 by formyl and hydroxymethyl substituents, respectively. Virtually absent from fresh foods, it is naturally generated in sugar-containing foods during storage, and especially by drying or cooking. It is the causative component in honey that affects the presystemic metabolism and pharmacokinetics of GZ in-vivo.	2.06	1	arenecarbaldehyde; furans; primary alcohol	indicator; Maillard reaction product
nogalamycin Nogalamycin: An anthrocycline from a Streptomyces nogalater variant. It is a cytolytic antineoplastic that inhibits DNA-dependent RNA synthesis by binding to DNA.. nogalamycin : An anthracycline antibiotic isolated from Streptomyces nogalater. It is a DNA intercalator and exhibits anticancer properties.	2.02	1
anisomycin Anisomycin: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.. (-)-anisomycin : An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.	2.01	1	monohydroxypyrrolidine; organonitrogen heterocyclic antibiotic	anticoronaviral agent; antimicrobial agent; antineoplastic agent; antiparasitic agent; bacterial metabolite; DNA synthesis inhibitor; protein synthesis inhibitor
benzofurans Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.	2.99	4
wortmannin [no description available]	2.03	1	acetate ester; cyclic ketone; delta-lactone; organic heteropentacyclic compound	anticoronaviral agent; antineoplastic agent; autophagy inhibitor; EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor; geroprotector; Penicillium metabolite; radiosensitizing agent
2-oxindole 2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.	3.8	10	gamma-lactam; indolinone
esermethole esermethole: structure in first source	2.11	1
curcuphenol curcuphenol: from marine sponge Epipolasis sp.; inhibts H,K-ATPase; structure given in first source; RN given refers to (R)-isomer	2.06	1
lithium chloride Lithium Chloride: A salt of lithium that has been used experimentally as an immunomodulator.. lithium chloride : A metal chloride salt with a Li(+) counterion.	2.07	1	inorganic chloride; lithium salt	antimanic drug; geroprotector
glyceraldehyde 3-phosphate Glyceraldehyde 3-Phosphate: An aldotriose which is an important intermediate in glycolysis and in tryptophan biosynthesis.. glyceraldehyde 3-phosphate : An aldotriose phosphate that is the 3-phospho derivative of glyceraldehyde. It is an important metabolic intermediate in several central metabolic pathways in all organisms.	2.21	1	glyceraldehyde 3-phosphate	mouse metabolite
5'-deoxyadenosine 5'-deoxyadenosine: main heading DEOXYADENOSINE refers to the 3' cpd. 5'-deoxyadenosine : A 5'-deoxyribonucleoside compound having adenosine as the nucleobase.	2.17	1	5'-deoxyribonucleoside; adenosines	Escherichia coli metabolite; human metabolite; mouse metabolite
ribulose 5-phosphate ribulose 5-phosphate: RN given refers to cpd without isomeric designation. D-ribulose 5-phosphate : The D-enantiomer of ribulose 5-phosphate that is one of the end-products of the pentose phosphate pathway.. ribulose 5-phosphate : A ribulose phosphate in which the phosphate group is attached at position 5.	2.42	2	ribulose 5-phosphate	mouse metabolite
xylulose-5-phosphate, (d)-isomer D-xylulose 5-phosphate : The D-enantiomer of xylulose 5-phosphate.	2	1	xylulose 5-phosphate	Escherichia coli metabolite; mouse metabolite
arabinose [no description available]	2	1	L-arabinose	Escherichia coli metabolite; mouse metabolite
n-acetylneuraminic acid N-Acetylneuraminic Acid: An N-acyl derivative of neuraminic acid. N-acetylneuraminic acid occurs in many polysaccharides, glycoproteins, and glycolipids in animals and bacteria. (From Dorland, 28th ed, p1518). N-acetylneuraminic acid : An N-acylneuraminic acid where the N-acyl group is specified as acetyl.	2.03	1	N-acetylneuraminic acids	antioxidant; bacterial metabolite; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor; human metabolite; mouse metabolite
glucosamine D-glucosamine : An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.. 2-amino-2-deoxy-D-glucopyranose : A D-glucosamine whose structure comprises D-glucopyranose having an amino substituent at position 2.	2.07	1	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
lyxose D-lyxose : Any lyxose having D-configuration.. D-lyxopyranose : The pyranose form of D-lyxose.	2.05	1	D-lyxose
pantolactone pantolactone: degradation product of pantothenic acid in liver; RN given refers to (+-)-isomer; structure. (R)-pantolactone : A butan-4-olide that is dihydrofuran-2(3H)-one substituted by a hydroxy group at position 3 and two methyl groups at position 4 (the R-stereoisomer).	2.48	2	butan-4-olide	Saccharomyces cerevisiae metabolite
tartaric acid tartaric acid: RN given refers to cpd with unspecified isomeric designation. D-tartaric acid : The D-enantiomer of tartaric acid.	2.1	1	tartaric acid	Escherichia coli metabolite
cortodoxone Cortodoxone: 17,21-Dihydroxypregn-4-ene-3,20-dione. A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities.. 11-deoxycortisol : A deoxycortisol that is cortisol in which the hydroxy group at position 11 has been replaced by a hydrogen.	1.94	1	deoxycortisol; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
quinidine Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.	2.06	1	cinchona alkaloid	alpha-adrenergic antagonist; anti-arrhythmia drug; antimalarial; drug allergen; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor; muscarinic antagonist; P450 inhibitor; potassium channel blocker; sodium channel blocker
erythronolide b [no description available]	2.05	1	erythronolide
griseofulvin Griseofulvin: An antifungal agent used in the treatment of TINEA infections.. griseofulvin : An oxaspiro compound produced by Penicillium griseofulvum. It is used by mouth as an antifungal drug for infections involving the scalp, hair, nails and skin that do not respond to topical treatment.	2.08	1	1-benzofurans; antibiotic antifungal drug; benzofuran antifungal drug; organochlorine compound; oxaspiro compound	antibacterial agent; Penicillium metabolite
monensin Monensin: An antiprotozoal agent produced by Streptomyces cinnamonensis. It exerts its effect during the development of first-generation trophozoites into first-generation schizonts within the intestinal epithelial cells. It does not interfere with hosts' development of acquired immunity to the majority of coccidial species. Monensin is a sodium and proton selective ionophore and is widely used as such in biochemical studies.. monensin A : A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by Streptomyces cinnamonensis. An antiprotozoal, it is used as the sodium salt as a feed additive for the prevention of coccidiosis in poultry and as a growth promoter in cattle.	2.31	1	cyclic hemiketal; monocarboxylic acid; polyether antibiotic; spiroketal	antifungal agent; coccidiostat; ionophore
physovenine physovenine: structure given in first source	2.11	1	indoles
altholactone altholactone: structure in first source	2.11	1	furopyran
lignans Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)	3.3	6
ao 128 AO 128: alpha-glucosidase inhibitor; structure given in first source	2.04	1	organic molecular entity
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.43	2	cyclodextrin
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	2.04	1	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
epothilone b [no description available]	2	1	epothilone; epoxide	antineoplastic agent; apoptosis inducer; microtubule-stabilising agent
benzene-1,3,5-tricarboxamide benzene-1,3,5-tricarboxamide: structure in first source	2.1	1
glycolaldehyde phosphate glycolaldehyde phosphate: structure. glycolaldehyde phosphate : A member of the class of aldehydes that is glycolaldehyde in which the hydroxy hydrogen has been replaced by a phospho group.	2.42	2	aldehyde; monoalkyl phosphate
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	1	epothilone; epoxide	antineoplastic agent; metabolite; microtubule-stabilising agent; tubulin modulator
imidazolidines [no description available]	2.44	2	azacycloalkane; imidazolidines; saturated organic heteromonocyclic parent
tetronic acid tetronic acid: structure; in fifth source	2.5	2
3-methyl-2,4-nonanedione 3-methyl-2,4-nonanedione: structure in first source	2	1	beta-diketone
oxazolidine oxazolidine: structure given in first source	2.01	1	oxazolidine
lyngbyaloside b lyngbyaloside B: a glycoside macrolide from a Palauan marine cyanobacterium, Lyngbya sp.; structure in first source	2.11	1
glycosides [no description available]	2.13	1
chalcone trans-chalcone : The trans-isomer of chalcone.	2.04	1	chalcone	EC 3.2.1.1 (alpha-amylase) inhibitor
stilbenes Stilbenes: Organic compounds that contain 1,2-diphenylethylene as a functional group.. trans-stilbene : The trans-isomer of stilbene.	2.41	1	stilbene
sorbic acid Sorbic Acid: Mold and yeast inhibitor. Used as a fungistatic agent for foods, especially cheeses.. (2E,4E)-hexa-2,4-dienoic acid : A sorbic acid having trans-double bonds at positions 2 and 4; a food preservative that can induce cutaneous vasodilation and stinging upon topical application to humans. It is the most thermodynamically stable of the four possible geometric isomers possible, as well as the one with the highest antimicrobial activity.. sorbic acid : A hexadienoic acid with double bonds at C-2 and C-4; it has four geometrical isomers, of which the trans,trans-form is naturally occurring.	2.06	1	alpha,beta-unsaturated monocarboxylic acid; sorbic acid
sesquiterpenes [no description available]	3.35	6
rhodotorulic acid rhodotorulic acid: RN given refers to (1S-cis)-isomer; structure. rhodotorulic acid : A member of the class of 2,5-diketopiperazines obtained by cyclodimerisation of N(5)-acetyl-N(5)-hydroxy-L-ornithine.	3.25	1	2,5-diketopiperazines; hydroxamic acid; L-ornithine derivative	fungal metabolite; siderophore
thiazoline-2-thione thiazoline-2-thione: carboxyl-activating reagent in peptide synthesis	3.29	6
2-mercaptothiazoline [no description available]	2.41	1
mucochloric acid [no description available]	2.03	1
thiourea Thiourea: A photographic fixative used also in the manufacture of resins. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), this substance may reasonably be anticipated to be a carcinogen (Merck Index, 9th ed). Many of its derivatives are ANTITHYROID AGENTS and/or FREE RADICAL SCAVENGERS.. thiourea : The simplest member of the thiourea class, consisting of urea with the oxygen atom substituted by sulfur.	3.72	9	one-carbon compound; thioureas; ureas	antioxidant; chromophore
D-fructopyranose [no description available]	2	1	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.13	1
ethyl trifluoropyruvate [no description available]	2.52	2
3,4-diaminocyclobut-3-ene-1,2-dione 3,4-diaminocyclobut-3-ene-1,2-dione: structure in first source	3.41	1
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	2.77	3	alkali metal atom
hydroxylysine Hydroxylysine: A hydroxylated derivative of the amino acid LYSINE that is present in certain collagens.. hydroxylysine : A hydroxy-amino acid in which the amino acid specified is lysine. A "closed" class.. erythro-5-hydroxy-L-lysine : A 5-hydroxylysine consisting of L-lysine having an (R)-hydroxy group at the 5-position.. 5-hydroxylysine : A hydroxylysine that is lysine substituted by a hydroxy group at position 5.	2.21	1	5-hydroxylysine; hydroxy-L-lysine	human metabolite
quinine [no description available]	3.97	3	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
beta-proline beta-proline: RN given refers to cpd without isomeric designation; structure given in first source	2.05	1
piperolactam a piperolactam A: isolated from Houttynia cordata; structure in first source	2.04	1	alkaloid
phosphonic acid phosphonic acid : A phosphorus oxoacid that consists of a single pentavalent phosphorus covalently bound via single bonds to a single hydrogen and two hydroxy groups and via a double bond to an oxygen. The parent of the class of phosphonic acids.	2.07	1
salinomycin salinomycin: from Streptomyces albus; RN given refers to parent cpd; structure	2.03	1	polyketide; spiroketal	animal growth promotant; potassium ionophore
naphthoquinones Naphthoquinones: Naphthalene rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.	2.53	2
sodium borohydride sodium borohydride: RN given refers to parent cpd	2.11	1	inorganic sodium salt; metal tetrahydridoborate
digitoxigenin Digitoxigenin: 3 beta,14-Dihydroxy-5 beta-card-20(22)enolide. A cardenolide which is the aglycon of digitoxin. Synonyms: Cerberigenin; Echujetin; Evonogenin; Thevetigenin.. digitoxigenin : A 5beta-cardenolide that is 5beta-cardanolide with hydroxy substituents at the 3beta- and 14beta-positions and double bond unsaturation at C(20)-C(22).	2.17	1	14beta-hydroxy steroid; 3beta-hydroxy steroid
australifungin australifungin: contains a combination of alpha-diketone and beta-ketoaldehyde groups; from Sporormiella australis; inhibits sphinganine N-acyltransferase (ceramide synthetase); structure given in first source. australifungin : A carbobicyclic compound that is 4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one substituted by hydroxy groups at positions 2, 5 and 8, a (2Z)-3-hydroxyprop-2-enoyl group at position 4, methyl groups at positions 4 and 7 and a 2R-octan-2-yl group at position 3 (the 4S,4aR,5S,7R,8R,8aS stereoisomer). It is isolated from the fermentation extracts of Sporormiella australis and exhibits antifungal activity by interfering with the fungal lipid metabolism.	2.13	1	carbobicyclic compound; enol; enone; secondary alcohol	antifungal agent; EC 2.3.1.24 (sphingosine N-acyltransferase) inhibitor; HIV-1 integrase inhibitor; metabolite
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	2.49	2	monocarboxylic acid; prostaglandins Falpha	human metabolite; mouse metabolite
glutaconic acid glutaconic acid: RN given refers to parent cpd without isomeric designation; structure. glutaconic acid : A pentenedioic acid that is pent-2-ene substituted by carboxy groups at positions 1 and 5.. (E)-glutaconic acid : The (E)-isomer of glutaconic acid.	2.04	1	glutaconic acid
maytansine Maytansine: An ansa macrolide isolated from the MAYTENUS genus of East African shrubs.. maytansine : An organic heterotetracyclic compound and 19-membered macrocyclic lactam antibiotic originally isolated from the Ethiopian shrub Maytenus serrata but also found in other Maytenus species. It exhibits cytotoxicity against many tumour cell lines.	2.05	1	alpha-amino acid ester; carbamate ester; epoxide; maytansinoid; organic heterotetracyclic compound; organochlorine compound	antimicrobial agent; antimitotic; antineoplastic agent; plant metabolite; tubulin modulator
beta-nitrostyrene beta-nitrostyrene: RN given refers to cpd without isomeric designation	2.07	1
reidispongiolide a reidispongiolide A: structure in first source	2.04	1
bimatoprost Bimatoprost: A cloprostenol-derived amide that is used as an ANTIHYPERTENSIVE AGENT in the treatment of OPEN-ANGLE GLAUCOMA and OCULAR HYPERTENSION.	2.11	1	monocarboxylic acid amide	antiglaucoma drug; antihypertensive agent
cloprostenol Cloprostenol: A synthetic prostaglandin F2alpha analog. The compound has luteolytic effects and is used for the synchronization of estrus in cattle.	2.11	1	prostanoid
cp 99994 3-(2-methoxybenzylamino)-2-phenylpiperidine: selective NK(1) receptor antagonist; CP-100263 is the inactive enantiomer	2.07	1
latanoprost Latanoprost: A prostaglandin F analog used to treat OCULAR HYPERTENSION in patients with GLAUCOMA.. latanoprost : A prostaglandin Falpha that is the isopropyl ester prodrug of latanoprost free acid. Used in the treatment of open-angle glaucoma and ocular hypertension.	2.11	1	isopropyl ester; prostaglandins Falpha; triol	antiglaucoma drug; antihypertensive agent; EC 4.2.1.1 (carbonic anhydrase) inhibitor; prodrug
fosbretabulin fosbretabulin: a microtubule destabilizing agent isolated from Combretum caffrum; structure in first source	2.41	1
tin [no description available]	2.45	2	carbon group element atom; elemental tin; metal atom	micronutrient
barium Barium: An element of the alkaline earth group of metals. It has an atomic symbol Ba, atomic number 56, and atomic weight 138. All of its acid-soluble salts are poisonous.	2.05	1	alkaline earth metal atom; elemental barium
lasalocid Lasalocid: Cationic ionophore antibiotic obtained from Streptomyces lasaliensis that, among other effects, dissociates the calcium fluxes in muscle fibers. It is used as a coccidiostat, especially in poultry.. lasalocid : A polyether antibiotic used for prevention and treatment of coccidiosis in poultry.	2.31	1	beta-hydroxy ketone; monocarboxylic acid; monohydroxybenzoic acid; oxanes; oxolanes; polyether antibiotic; secondary alcohol; tertiary alcohol	bacterial metabolite; coccidiostat; ionophore
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.	2.76	3	chalcogen; nonmetal atom	macronutrient
geldanamycin [no description available]	2.01	1
2-pentenal 2-pentenal: RN given refers to cpd without isomeric designation. 2-pentenal : An enal consisting of pent-2-ene having an oxo group at the 1-position. (E)-2-pentenal : A 2-pentenal in which the double bond has (E)-configuration. It is found in cigarette smoke, virgin olive oil, and milk.	2.1	1	2-pentenal	plant metabolite
deoxyribose [no description available]	2.17	1	deoxypentose	human metabolite; mouse 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.	2.11	1	cysteinium	fundamental metabolite
silicon Silicon: A trace element that constitutes about 27.6% of the earth's crust in the form of SILICON DIOXIDE. It does not occur free in nature. Silicon has the atomic symbol Si, atomic number 14, and atomic weight [28.084; 28.086].	2.82	3	carbon group element atom; metalloid atom; nonmetal atom
boron Boron: A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY.	4.46	6	boron group element atom; metalloid atom; nonmetal atom	micronutrient
cystothiazole a cystothiazole A: a bithiazole-type antibiotic isolated from Cystobacter fuscus; structure in first source. cystothiazole A : An organonitrogen heterocyclic antibiotic that is 2,4'-bi-1,3-thiazole substituted by an isopropyl group at position 2' and a 3,5,7-trimethoxy-4-methyl-7-oxohepta-1,5-dien-1-yl group at position 4 (the 2E,4R,5S,6E stereoisomer). It is isolated from the culture broth of myxobacterium, Cystobacter fuscus, and exhibits antifungal and cytotoxic activity.	2.07	1	1,3-thiazoles; biaryl; enoate ester; enol ether; methyl ester; organonitrogen heterocyclic antibiotic	antifungal agent; antineoplastic agent; bacterial metabolite
tedanolide tedanolide: cytotoxic compound from sponge, Tedania ignis; structure in first source	2.42	2
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2.1	1	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
pironetin pironetin: a microbial secondary metabolite having the activity of shortening plant height from Streptomyces sp.; structure in first source	2.05	1	aliphatic alcohol
fd 891 FD 891: an 18-membered macrolide with an epoxide ring at C8 and C9; the epoxide may play an important role in its cytocidal activity; structure given in first source	2.1	1
beta-escin [no description available]	2.31	1
lactacystin [no description available]	2.05	1	lactam; S-substituted L-cysteine
mannich bases Mannich Bases: Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.	2.77	3
conagenin conagenin: from Streptomyces roseosporus; structure given in first source	2.05	1
2,2,2-trifluorodiazoethane 2,2,2-trifluorodiazoethane: structure in first source	2.1	1
zeolites [no description available]	2.08	1
hamigeran b hamigeran B: has antiviral activity; structure in first source	2.05	1
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	2.11	1
macquarimicin a macquarimicin A: isolated from Micromonospora; structure in first source	3.16	1
haouamine a haouamine A: from ascidian Aplidium haouarianum; structure in first source	2.21	1
spectaline spectaline: structure in first source	2.02	1
pestalotiopsin a pestalotiopsin A: structure in first source	2.05	1
belactosin c belactosin C: isolated from Streptomyces; structure in first source	2.03	1
homocamptothecin homocamptothecin: a DNA topoisomerase I antagonists, is a semisynthetic analogue of camptothecin (CPT) with a seven-membered beta-hydroxylactone resulting from the insertion of a mehthylene spacer between the alcohol moiety and the carboxyl function of the naturally occurring six-membered alpha-hydroxylactone of CPT; structure in first source	2.03	1	epsilon-lactone; organic heteropentacyclic compound; organonitrogen heterocyclic compound; tertiary alcohol	antineoplastic agent; EC 5.99.1.2 (DNA topoisomerase) inhibitor
calyciphylline a calyciphylline A: a hexacyclic alkaloid from Daphniphyllum calycinum; structure in first source	2.41	1
horsfiline horsfiline: structure in first source	2.11	1
marizomib marizomib: a proteasome inhibitor from a marine bacterium Salinospora; structure in first source	2.08	1	beta-lactone; gamma-lactam; organic heterobicyclic compound; organochlorine compound; salinosporamide	antineoplastic agent; proteasome inhibitor
peloruside a peloruside A: Antibiotics, Antineoplastic from the sponge Mycale; structure in first source. peloruside A : A macrolide that is a novel secondary metabolite isolated from a New Zealand marine sponge, Mycale hentscheli.	2.48	2
er-086526 eribulin: a halichondrin B derivative that suppresses microtubule growth and acts as an antimitotic agent; structure in first source. eribulin : A fully synthetic macrocyclic ketone analogue of marine sponge natural products. Inhibits growth phase of microtubules via tubulin-based antimitotic mechanism, which leads to G2/M cell-cycle block, disruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage	2.11	1	cyclic ketal; cyclic ketone; macrocycle; polycyclic ether; polyether; primary amino compound	antineoplastic agent; microtubule-destabilising agent
caprazol caprazol: an antituberculosis antibiotic; isolated from Streptomyces; structure in first source	2.1	1
talaumidin talaumidin: a neolignan from Aristolochia arcuata; structure in first source	2.05	1
glyoxamide glyoxamide : The simplest of the class of glyoxamides, with no substitution on nitrogen.	2.03	1	glyoxamides
zincophorin zincophorin: 25 carbon polypropionate from Streptomyces griseus; griseochelin and M 144255 are the same monocarboxylic acid ionophore	2.06	1	pyrans	bacterial metabolite; ionophore
tedanolide c tedanolide C: 18-membered-ring cytotoxic macrolide isolated from the Papua New Guinea marine sponge; structure in first source	2.06	1
dextrothyroxine [no description available]	2.1	1
coerulescine coerulescine: structure in first source	2.11	1
1,4-dihydroquinoline 1,4-dihydroquinoline: structure in first source	2.07	1
3-hydroxypipecolic acid 3-hydroxypipecolic acid: glycosidase inhibitor; structure in first source	2.07	1
hypocrellin a hypocrellin A: isolated from fungus Hypocrella bambusae sacc	2.05	1
discodermolide discodermolide: a lactone-bearing polyhydroxylated alkatetraene from the marine sponge Discodermia dissoluta; microtubule-stabilizing agent like taxol	2.7	3
inthomycin c inthomycin C: from Streptomyces sp,; structure in first source	2.05	1
oligonucleotides [no description available]	2.02	1
iriomoteolide-1a iriomoteolide-1a: from a benthic dinoflagellate amphidinium species; structure in first source	2.46	2	macrolide
palmerolide a palmerolide A: isolated from the antarctic marine tunicate Synoicum adareanum; structure in first source	2.08	1
aminoindanol aminoindanol: structure in first source	2.04	1
sapogenins Sapogenins: The aglucon moiety of a saponin molecule. It may be triterpenoid or steroid, usually spirostan, in nature.	2.15	1
chitosan [no description available]	2.69	2
marmycin a marmycin A: cytotoxic compound from a marine sediment-derived actinomycete related to the genus Streptomyces; structure in first source	2.06	1
sodium hypochlorite Sodium Hypochlorite: It is used as an oxidizing and bleaching agent and as a disinfectant. (From Grant & Hackh's Chemical Dictionary, 5th ed). sodium hypochlorite : An inorganic sodium salt in which hypochlorite is the counterion. It is used as a bleaching and disinfecting agent and is commonly found in household bleach.	2	1	inorganic sodium salt	bleaching agent; disinfectant
s-adenosylmethionine (R)-S-adenosyl-L-methionine : An S-adenosyl-L-methionine that has R-configuration.. S-adenosyl-L-methionine zwitterion : A zwitterionic tautomer of S-adenosyl-L-methionine arising from shift of the proton from the carboxy group to the amino group.. (R)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has R-configuration; major species at pH 7.3.. (S)-S-adenosyl-L-methionine zwitterion : An S-adenosyl-L-methionine zwitterion that has S-configuration; major species at pH 7.3.. S-adenosyl-L-methionine : A sulfonium compound that is the S-adenosyl derivative of L-methionine. It is an intermediate in the metabolic pathway of methionine.	2.17	1	organic cation; sulfonium compound	coenzyme; cofactor; human metabolite; micronutrient; Mycoplasma genitalium metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
mb 5 malbrancheamide B: from the culture medium and mycelia of the ascomycete Malbranchea aurantiaca; structure in first source	2.07	1
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	2.15	1
meiogynin a meiogynin A: from the bark of Meiogyne cylindrocarpa; structure in first source	2.11	1
piperidines Piperidines: A family of hexahydropyridines.	2.76	3
madindoline a madindoline A: inhibits interleukin-6; isolated from Streptomyces; structure in first source	2.05	1
aspirochlorine aspirochlorine: inhibitor of fungal protein synthesis; structure in first source	2.17	1	organic heterotetracyclic compound	Aspergillus metabolite
tylosin [no description available]	2.03	1
mycalamide a mycalamide A: structure given in first source; RN given refers to (2R-(2alpha,2(S(S)),5beta,6beta))-isomer; isolated from marine sponges	2.03	1	disaccharide
cyanolide a cyanolide A: molluscicidal from the Papua New Guinea cyanobacterium Lyngbya bouillonii; structure in first source	2.06	1
solanoeclepin a solanoeclepin A: the most active natural hatching agent of potato cyst; structure in first source	2.1	1
crotylsilane crotylsilane: structure in first source	2.05	1
oxytetracycline, anhydrous Oxytetracycline: A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES RIMOSUS and used in a wide variety of clinical conditions.. oxytetracycline : A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.	2.03	1
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2.52	2	benzenes; hydroxycoumarin; methyl ketone
tetramic acid tetramic acid : A gamma-lactam that is 1,3-dihydro-2H-pyrrol-2-one in which the hydrogen at position 4 has been replaced by a hydroxy group. Despite its simple structure, it was not synthesised until 1972; earlier attempts were later shown to have resulted only in the formation of the isomer 5-imino-4,5-dihydrofuran-3-ol.	2.1	1
aflastatin a aflastatin A: inhibitor of aflatoxin production by aflatoxigenic fungi; from Streptomyces sp.; structure given in first source	2.41	1
microcystin microcystin: microcystins have the general structure cyclo(D-Ala-L-X-D-erythro--methylisoasp-L-Y-Adda-D-isoGlu-N-methyldehydroAla) where X and Y are variable L-amino acids;. microcystin : A family of cyclic heptapeptide hepatotoxins produced by a number of cyanobacteria, the most notable of which is Microcystis, from which the name of the family is derived. Microcystins consist of a heptapeptide macrocycle made up of five non-protein amino acids and two protein amino acids.	2.05	1	peptide
brine brine: not from seawater; contains sodium chloride; calcium chloride; magnesium chloride; one or all of the above	2.07	1
doravirine [no description available]	2.11	1
oxazaborolidinone oxazaborolidinone: structure in first source	2.04	1
hippolachnin a hippolachnin A: from the South China Sea sponge Hippospongia lachne; structure in first source	2.13	1
histidinohydroxylysinonorleucine histidinohydroxylysinonorleucine: major cross-link of skin collagen in patients with amyotrophic lateral sclerosis	2.21	1
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.04	1
spirolide c spirolide C: isolated from contaminated scallops and phytoplankton collections obtained from a Nova Scotian aquaculture site, as well as from batch cultures of the dinoflagellate Alexandrium ostenfeldii obtained as a single-cell isolate from these phytoplankton assemblages; structure in first source	2.05	1	azepine
phaeosphaeride a phaeosphaeride A: inhibits STAT3-dependent signaling; structure in first source	2.06	1
haloperidol diphenylprolinol silyl ether: structure in first source	2.13	1
leucinostatin a leucinostatin A: isolated from Penicillium lilacinum; A 20668 A,B,& C are polypeptide antibiotics that inhibit phosphorylation of ADP, Mg ATPase; RN given refers to leucinostatin A	2.15	1
levoleucovorin Levoleucovorin: A folate analog consisting of the pharmacologically active isomer of LEUCOVORIN.. (6S)-5-formyltetrahydrofolic acid : The pharmacologically active (6S)-stereoisomer of 5-formyltetrahydrofolic acid.	2.01	1	5-formyltetrahydrofolic acid	antineoplastic agent; metabolite
guanosine ribonucleoside : Any nucleoside where the sugar component is D-ribose.	2.41	1	guanosines; purines D-ribonucleoside	fundamental metabolite
avermectin avermectin: produced by actinomycete, Streptomyces avermitilis; structure; see also records for specific avermectins. avermectin : Any of the macrolides obtained as fermentation products from the bacterium Streptomyces avermitilis and consisting of a 16-membered macrocyclic backbone that is fused both benzofuran and spiroketal functions and contains a disaccharide substituent. They have significant anthelmintic and insecticidal properties.	2.1	1
enterocin enterocin: antibiotic isolated from Streptomyces candidus var. enterostaticus WS-8096 & Streptomyces viridochromogenes M-127; molecular formula: C22-H20-010; structure	2.21	1
pseudolaric acid a pseudolaric acid A: from Pseudolarix kaempfer Gordon; structure given in first source	2.03	1
thuggacin b thuggacin B: structure in first source	2.1	1
neaumycin b neaumycin B: isolated from the soil actinomycete Streptomyces sp. NEAU-x211; structure in first source	2.41	1
pyrimidinones Pyrimidinones: Heterocyclic compounds known as 2-pyrimidones (or 2-hydroxypyrimidines) and 4-pyrimidones (or 4-hydroxypyrimidines) with the general formula C4H4N2O.	2.07	1
callipeltoside a callipeltoside A: isolated from the sponge Callipelta; structure in first source	3.16	1
viridinomycin viridinomycin: crystalline antibiotic isolated from culture broth of Streptomyces viridochromogenes strain no. T-24146	2.03	1
phenanthrenes Phenanthrenes: POLYCYCLIC AROMATIC HYDROCARBONS composed of three fused BENZENE rings.. phenanthrenes : Any benzenoid aromatic compound that consists of a phenanthrene skeleton and its substituted derivatives thereof.	2.04	1

Condition	Relationship Strength	Studies
Complications of Diabetes Mellitus [description not available]	2.15	1
Infections, Plasmodium [description not available]	2.17	1
Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.	2.17	1
Bacterial Disease [description not available]	2.08	1
Fungal Diseases [description not available]	2.08	1
Bacterial Infections Infections by bacteria, general or unspecified.	2.08	1
Mycoses Diseases caused by FUNGI.	2.08	1
HIV Coinfection [description not available]	2.11	1
HIV Infections Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).	2.11	1
Acute Confusional Senile Dementia [description not available]	2.13	1
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.13	1
Cancer of Prostate [description not available]	2.06	1
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	2.06	1

3-hydroxybutanal

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