Page last updated: 2024-10-24

regulation of bile acid biosynthetic process

Definition

Target type: biologicalprocess

Any process that modulates the frequency, rate or extent of the chemical reactions and pathways resulting in the formation of bile acids. [GOC:BHF, GOC:mah]

The biosynthesis of bile acids, essential for lipid digestion and cholesterol homeostasis, is a tightly regulated process involving multiple steps and feedback mechanisms. The primary site of bile acid synthesis is the liver, where cholesterol is converted into bile acids through a series of enzymatic reactions. The process begins with the hydroxylation of cholesterol by the enzyme cholesterol 7α-hydroxylase (CYP7A1), the rate-limiting step in bile acid synthesis. This step is subject to both positive and negative regulation.

**Positive regulation:**

* **Increased demand for bile acids:** Factors such as high-fat meals and low levels of bile acids in the intestine stimulate the production of bile acids. This is mediated by the release of hormones like cholecystokinin (CCK) and the activation of nuclear receptors such as FXR (farnesoid X receptor).
* **Insulin:** Insulin promotes bile acid synthesis, potentially through its effect on hepatic lipid metabolism.

**Negative regulation:**

* **Feedback inhibition:** Bile acids themselves act as feedback inhibitors of their own synthesis. When bile acid levels in the intestine rise, they bind to FXR, which activates the expression of the gene encoding for the protein SHP (small heterodimer partner). SHP, in turn, suppresses the expression of CYP7A1, effectively reducing bile acid synthesis.
* **Other regulatory factors:** The expression of CYP7A1 is also regulated by other factors, such as thyroid hormone, inflammatory cytokines, and certain medications.

**Beyond the initial hydroxylation:**

Following the conversion of cholesterol to 7α-hydroxycholesterol, a series of enzymatic reactions modify the molecule, resulting in the formation of primary bile acids like cholic acid and chenodeoxycholic acid. These bile acids are then conjugated to glycine or taurine, making them more water-soluble and facilitating their secretion into bile.

**Bile acid secretion and enterohepatic circulation:**

Bile acids are secreted into the bile canaliculi and flow into the gallbladder for storage and concentration. Following a meal, the gallbladder contracts and releases bile into the duodenum, where it aids in the digestion and absorption of fats. After their role in lipid digestion, bile acids are reabsorbed from the ileum and transported back to the liver via the portal vein. This process, known as enterohepatic circulation, is crucial for maintaining a constant pool of bile acids in the body and conserving cholesterol.

**In summary:**

The biosynthesis of bile acids is a complex process involving multiple enzymes, regulatory molecules, and feedback mechanisms. The regulation of this process is essential for maintaining normal lipid metabolism and preventing the accumulation of cholesterol in the body. Disruptions in this regulatory network can lead to various diseases, including gallstones, cholestasis, and liver disease.'
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Proteins (4)

ProteinDefinitionTaxonomy
Bile acid receptorA bile acid receptor that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q96RI1]Homo sapiens (human)
NAD-dependent protein deacetylase sirtuin-1An NAD-dependent protein deacetylase sirtuin-1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:Q96EB6]Homo sapiens (human)
Liver carboxylesterase 1A liver carboxylesterase 1 that is encoded in the genome of human. [PRO:DNx, UniProtKB:P23141]Homo sapiens (human)
Fibroblast growth factor receptor 4A fibroblast growth factor receptor 4 that is encoded in the genome of human. [PRO:CNA]Homo sapiens (human)

Compounds (260)

CompoundDefinitionClassesRoles
bis(4-nitrophenyl)phosphatebis(4-nitrophenyl)phosphate: RN given refers to parent cpdaryl phosphate
4-methylumbelliferyl acetate4-methylumbelliferyl acetate : An acetate ester consiting of umbelliferone carrying a 7-O-acetyl group.acetate ester;
coumarins
plant metabolite
diacetylbutane-2,3-dione : An alpha-diketone that is butane substituted by oxo groups at positions 2 and 3. It is a metabolite produced during the malolactic fermentation.alpha-diketoneEscherichia coli metabolite;
Saccharomyces cerevisiae metabolite
niacinamidenicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group.pyridine alkaloid;
pyridinecarboxamide;
vitamin B3
anti-inflammatory agent;
antioxidant;
cofactor;
EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
Escherichia coli metabolite;
geroprotector;
human urinary metabolite;
metabolite;
mouse metabolite;
neuroprotective agent;
Saccharomyces cerevisiae metabolite;
Sir2 inhibitor
pd 173074aromatic amine;
biaryl;
dimethoxybenzene;
pyridopyrimidine;
tertiary amino compound;
ureas
antineoplastic agent;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
fibroblast growth factor receptor antagonist
6,7-dichloroquinoxaline-2,3-dionequinoxaline derivative
tacrinetacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.

Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.
acridines;
aromatic amine
EC 3.1.1.7 (acetylcholinesterase) inhibitor
ethacridineEthacridine: A topically applied anti-infective agent.acridines
aniracetamN-acylpyrrolidine;
pyrrolidin-2-ones
benzbromaronebenzbromarone : 1-Benzofuran substituted at C-2 and C-3 by an ethyl group and a 3,5-dibromo-4-hydroxybenzoyl group respectively. An inhibitor of CYP2C9, it is used as an anti-gout medication.

Benzbromarone: Uricosuric that acts by increasing uric acid clearance. It is used in the treatment of gout.
1-benzofurans;
aromatic ketone
uricosuric drug
bisindolylmaleimide ibisindolylmaleimide I: a bis(indolyl)maleimide
bisindolylmaleimide vbisindolylmaleimide V: used as a negative control compound for protein kinase C inhibition; structure in first source;indoles
camostatcamostat : A benzoate ester resulting from the formal condensation of the carboxy group of 4-guanidinobenzoic acid with the hydroxy group of 2-(dimethylamino)-2-oxoethyl (4-hydroxyphenyl)acetate. It is a potent inhibitor of the human transmembrane protease serine 2 (TMPRSS2) and its mesylate salt is currently under investigation for its effectiveness in COVID-19 patients.benzoate ester;
carboxylic ester;
diester;
guanidines;
tertiary carboxamide
anti-inflammatory agent;
anticoronaviral agent;
antifibrinolytic drug;
antihypertensive agent;
antineoplastic agent;
antiviral agent;
serine protease inhibitor
clotrimazoleconazole antifungal drug;
imidazole antifungal drug;
imidazoles;
monochlorobenzenes
antiinfective agent;
environmental contaminant;
xenobiotic
dilazepdilazep : A member of the class of diazepanes that is 1,4-diazepane substituted by 3-[(3,4,5-trimethoxybenzoyl)oxy]propyl groups at positions 1 and 4. It is a potent adenosine uptake inhibitor that exhibits antiplatelet, antianginal and vasodilator properties.

Dilazep: Coronary vasodilator with some antiarrhythmic activity.
benzoate ester;
diazepane;
diester;
methoxybenzenes
cardioprotective agent;
platelet aggregation inhibitor;
vasodilator agent
benzophenonebenzophenone : The simplest member of the class of benzophenones, being formaldehyde in which both hydrogens are replaced by phenyl groups.benzophenonesphotosensitizing agent;
plant metabolite
valproic acidvalproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.

Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.
branched-chain fatty acid;
branched-chain saturated fatty acid
anticonvulsant;
antimanic drug;
EC 3.5.1.98 (histone deacetylase) inhibitor;
GABA agent;
neuroprotective agent;
psychotropic drug;
teratogenic agent
donepezil2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxyindan-1-one : A member of the class of indanones that is 5,6-dimethoxyindan-1-one which is substituted at position 2 by an (N-benzylpiperidin-4-yl)methyl group.

donepezil : A racemate comprising equimolar amounts of (R)- and (S)-donepezil. A centrally acting reversible acetylcholinesterase inhibitor, its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.

Donepezil: An indan and piperidine derivative that acts as a selective and reversible inhibitor of ACETYLCHOLINESTERASE. Donepezil is highly selective for the central nervous system and is used in the management of mild to moderate DEMENTIA in ALZHEIMER DISEASE.
aromatic ether;
indanones;
piperidines;
racemate
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
nootropic agent
felodipinefelodipine : The mixed (methyl, ethyl) diester of 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid. A calcium-channel blocker, it lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels. It is used in the management of hypertension and angina pectoris.

Felodipine: A dihydropyridine calcium antagonist with positive inotropic effects. It lowers blood pressure by reducing peripheral vascular resistance through a highly selective action on smooth muscle in arteriolar resistance vessels.
dichlorobenzene;
dihydropyridine;
ethyl ester;
methyl ester
anti-arrhythmia drug;
antihypertensive agent;
calcium channel blocker;
vasodilator agent
flutrimazoleflutrimazole : An imidazole antifungal agent that is imidazole in which the hydrogen attached to the nitrogen is replaced by a 2,4'-difluorotrityl group. A topical antifungal agent which displays potent broad-spectrum in vitro activity against dermatophytes, filamentous fungi and yeasts.imidazole antifungal drug;
imidazoles;
monofluorobenzenes
EC 1.14.13.70 (sterol 14alpha-demethylase) inhibitor
beta-lapachonebeta-lapachone : A benzochromenone that is 3,4-dihydro-2H-benzo[h]chromene-5,6-dione substituted by geminal methyl groups at position 2. Isolated from Tabebuia avellanedae, it exhibits antineoplastic and anti-inflammatory activities.

beta-lapachone: antineoplastic inhibitor of reverse transcriptase, DNA topoisomerase, and DNA polymerase
benzochromenone;
orthoquinones
anti-inflammatory agent;
antineoplastic agent;
plant metabolite
loratadineloratadine : A benzocycloheptapyridine that is 6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine substituted by a chloro group at position 8 and a 1-(ethoxycarbonyl)piperidin-4-ylidene group at position 11. It is a H1-receptor antagonist commonly employed in the treatment of allergic disorders.

Loratadine: A second-generation histamine H1 receptor antagonist used in the treatment of allergic rhinitis and urticaria. Unlike most classical antihistamines (HISTAMINE H1 ANTAGONISTS) it lacks central nervous system depressing effects such as drowsiness.
benzocycloheptapyridine;
ethyl ester;
N-acylpiperidine;
organochlorine compound;
tertiary carboxamide
anti-allergic agent;
cholinergic antagonist;
geroprotector;
H1-receptor antagonist
meperidineMeperidine: A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration.

pethidine : A piperidinecarboxylate ester that is piperidine which is substituted by a methyl group at position 1 and by phenyl and ethoxycarbonyl groups at position 4. It is an analgesic which is used for the treatment of moderate to severe pain, including postoperative pain and labour pain.
ethyl ester;
piperidinecarboxylate ester;
tertiary amino compound
antispasmodic drug;
kappa-opioid receptor agonist;
mu-opioid receptor agonist;
opioid analgesic
entinostatbenzamides;
carbamate ester;
primary amino compound;
pyridines;
substituted aniline
antineoplastic agent;
apoptosis inducer;
EC 3.5.1.98 (histone deacetylase) inhibitor
fenamic acidfenamic acid : An aminobenzoic acid that is the N-phenyl derivative of anthranilic acid. It acts as a parent skeleton for the synthesis of several non-steroidal anti-inflammatory drugs.

fenamic acid: has chloride and potassium channel-blocking activity; RN given refers to parent cpd
aminobenzoic acid;
secondary amino compound
membrane transport modulator
nimodipinenimodipine : A dihydropyridine that is 1,4-dihydropyridine which is substituted by methyl groups at positions 2 and 6, a (2-methoxyethoxy)carbonyl group at position 3, a m-nitrophenyl group at position 4, and an isopropoxycarbonyl group at position 5. An L-type calcium channel blocker, it acts particularly on cerebral circulation, and is used both orally and intravenously for the prevention and treatment of subarachnoid hemorrhage from ruptured intracranial aneurysm.

Nimodipine: A calcium channel blockader with preferential cerebrovascular activity. It has marked cerebrovascular dilating effects and lowers blood pressure.
2-methoxyethyl ester;
C-nitro compound;
dicarboxylic acids and O-substituted derivatives;
diester;
dihydropyridine;
isopropyl ester
antihypertensive agent;
calcium channel blocker;
cardiovascular drug;
vasodilator agent
quinone1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.

benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.

quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).
1,4-benzoquinonescofactor;
human xenobiotic metabolite;
mouse metabolite
ono 1078pranlukast: SRS-A antagonist; leukotriene D4 receptor antagonistchromones
raloxifeneraloxifene : A member of the class of 1-benzothiophenes that is 1-benzothiophene in which the hydrogens at positions 2, 3, and 6 have been replaced by p-hydroxyphenyl, p-[2-(piperidin-1-yl)ethoxy]benzoyl, and hydroxy groups, respectively.1-benzothiophenes;
aromatic ketone;
N-oxyethylpiperidine;
phenols
bone density conservation agent;
estrogen antagonist;
estrogen receptor modulator
ro 31-8220Ro 31-8220: a protein kinase C inhibitorimidothiocarbamic ester;
indoles;
maleimides
EC 2.7.11.13 (protein kinase C) inhibitor
sb 2021904-(4-fluorophenyl)-2-(4-hydroxyphenyl)-5-(4-pyridyl)imidazole: structure given in first source; inhibits p38 MAP kinaseimidazoles;
organofluorine compound;
phenols;
pyridines
apoptosis inducer;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
fenofibratebenzochromenone;
delta-lactone;
naphtho-alpha-pyrone
platelet aggregation inhibitor;
Sir2 inhibitor
imatinibaromatic amine;
benzamides;
N-methylpiperazine;
pyridines;
pyrimidines
antineoplastic agent;
apoptosis inducer;
tyrosine kinase inhibitor
sulconazole1-{2-[(4-chlorobenzyl)sulfanyl]-2-(2,4-dichlorophenyl)ethyl}-1H-imidazole : A member of the class of imidazoles that is 1-ethyl-1H-imidazole in which one of the hydrogens of the methyl group is replaced by a (4-chlorobenzyl)sulfanediyl group while a second is replaced by a 2,4-dichlorophenyl group.

sulconazole : A racemate comprising equimolar amounts of (R)- and (S)-sulconazole. An antifungal agent with activity against Candida species, it is used (generally as the nitrate salt) for the topical treatment of fungal skin infections.

sulconazole: RN given refers to cpd with unspecified isomeric designation; structure given in first source
dichlorobenzene;
imidazoles;
monochlorobenzenes;
organic sulfide
suraminsuramin : A member of the class of phenylureas that is urea in which each of the amino groups has been substituted by a 3-({2-methyl-5-[(4,6,8-trisulfo-1-naphthyl)carbamoyl]phenyl}carbamoyl)phenyl group. An activator of both the rabbit skeletal muscle RyR1 and sheep cardiac RyR2 isoform ryanodine receptor channels, it has been used for the treatment of human African trypanosomiasis for over 100 years.

Suramin: A polyanionic compound with an unknown mechanism of action. It is used parenterally in the treatment of African trypanosomiasis and it has been used clinically with diethylcarbamazine to kill the adult Onchocerca. (From AMA Drug Evaluations Annual, 1992, p1643) It has also been shown to have potent antineoplastic properties.
naphthalenesulfonic acid;
phenylureas;
secondary carboxamide
angiogenesis inhibitor;
antinematodal drug;
antineoplastic agent;
apoptosis inhibitor;
EC 2.7.11.13 (protein kinase C) inhibitor;
GABA antagonist;
GABA-gated chloride channel antagonist;
purinergic receptor P2 antagonist;
ryanodine receptor agonist;
trypanocidal drug
thyroxinethyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions.

Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.
2-halophenol;
iodophenol;
L-phenylalanine derivative;
non-proteinogenic L-alpha-amino acid;
thyroxine;
thyroxine zwitterion
antithyroid drug;
human metabolite;
mouse metabolite;
thyroid hormone
nadNADgeroprotector
acrylamideacrylamides;
N-acylammonia;
primary carboxamide
alkylating agent;
carcinogenic agent;
Maillard reaction product;
mutagen;
neurotoxin
acenaphthenequinoneacenaphthoquinone : An orthoquinone that is the 1,2-dioxo derivative of acenaphthene.orthoquinoneschain carrier;
epitope
9,10-phenanthrenequinone9,10-phenanthrenequinone: structurephenanthrenes
5-bromoisatinindolesanticoronaviral agent
isatintribulin: 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;indoledioneEC 1.4.3.4 (monoamine oxidase) inhibitor;
plant metabolite
4-tert-butylbenzoic acid4-tert-butylbenzoic acid: RN given refers to parent cpdalkylbenzene
chloranilChloranil: A quinone fungicide used for treatment of seeds and foliage.

tetrachloro-1,4-benzoquinone : A member of the class of 1,4-benzoquiones that is 1,4-benzoquinone in which all four hydrogens are substituted by chlorines.
1,4-benzoquinones;
organochlorine compound
EC 2.7.1.33 (pantothenate kinase) inhibitor;
metabolite
benzoinbenzoins;
secondary alpha-hydroxy ketone
EC 3.1.1.1 (carboxylesterase) inhibitor
dibenzoylmethanedibenzoylmethane : A beta-diketone that is acetylacetone (acac) in which both methyl groups have been replaced by phenyl groups. It is a minor constituent of the root extract of licorice (Glycyrrhiza glabra) and exhibits antimutagenic and anticancer effects.aromatic ketone;
beta-diketone
antimutagen;
antineoplastic agent;
metabolite
suramin sodiumsuramin sodium : An organic sodium salt that is the hexasodium salt of suramin. It is an FDA approved drug for African sleeping sickness and river blindness.organic sodium saltangiogenesis inhibitor;
antinematodal drug;
antineoplastic agent;
apoptosis inhibitor;
EC 2.7.11.13 (protein kinase C) inhibitor;
GABA antagonist;
GABA-gated chloride channel antagonist;
purinergic receptor P2 antagonist;
ryanodine receptor agonist;
trypanocidal drug
benzilbenzil : An alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively.

benzil: structure
alpha-diketone;
aromatic ketone
lithocholic acidlithocholate : A bile acid anion that is the conjugate base of lithocholic acid.

lithocholic acid : A monohydroxy-5beta-cholanic acid with a alpha-hydroxy substituent at position 3. It is a bile acid obtained from chenodeoxycholic acid by bacterial action.

Lithocholic Acid: A bile acid formed from chenodeoxycholate by bacterial action, usually conjugated with glycine or taurine. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is used as cholagogue and choleretic.
bile acid;
C24-steroid;
monohydroxy-5beta-cholanic acid
geroprotector;
human metabolite;
mouse metabolite
phenyl trifluoromethyl ketonephenyl trifluoromethyl ketone: converted to trifluoroacetic acid in water
chenodeoxycholic acidchenodeoxycholate : Conjugate base of chenodeoxycholic acid; major species at pH 7.3.

chenodeoxycholic acid : A dihydroxy-5beta-cholanic acid that is (5beta)-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 7 respectively.

Chenodeoxycholic Acid: A bile acid, usually conjugated with either glycine or taurine. It acts as a detergent to solubilize fats for intestinal absorption and is reabsorbed by the small intestine. It is used as cholagogue, a choleretic laxative, and to prevent or dissolve gallstones.
bile acid;
C24-steroid;
dihydroxy-5beta-cholanic acid
human metabolite;
mouse metabolite
1,3-cyclohexanedione1,3-cyclohexanedione: structure

cyclohexane-1,3-dione : A cyclohexanedione carrying oxo substituents at positions 1 and 3.
beta-diketone;
cyclohexanedione
oleanolic acidhydroxy monocarboxylic acid;
pentacyclic triterpenoid
plant metabolite
dibromsalicildibromsalicil: brominated salicyclic acid deriv; antiplaque antiseptic
1,2-naphthoquinone1,2-naphthoquinone : The parent structure of the family of 1,2-naphthoquinones, in which the oxo groups of the quinone moiety are at positions 1 and 2 of the naphthalene ring. It is a metabolite of naphthalene and is found in diesel exhaust particles.

naphthalene-1,2-dione: structure given in first source
1,2-naphthoquinonesaryl hydrocarbon receptor agonist;
carcinogenic agent
1-acetylisatin1-acetylisatin: structure in first sourceindoledione
1-phenyl-1,2-propanedione1-phenyl-1,2-propanedione : An alpha-diketone that consists of 1-phenylpropane bearing keto substituents at positions 1 and 2. It is found in coffee.

1-phenyl-1,2-propanedione: an oxoglutarate carrier antagonist
alpha-diketone;
aromatic ketone
plant metabolite
2,3-pentanedionepentane-2,3-dione : An alpha-diketone that is pentane substituted at the 2- and 3-positions by oxo groups.alpha-diketone;
methyl ketone
flavouring agent
5-methylisatin5-methylisatin: structure in first source
glycochenodeoxycholic acidglycochenodeoxycholate : A N-acylglycinate that is the conjugate base of glycochenodeoxycholic acid.

glycochenodeoxycholic acid : A bile acid glycine conjugate having 3alpha,7alpha-dihydroxy-5beta-cholan-24-oyl as the bile acid component.

Glycochenodeoxycholic Acid: A bile salt formed in the liver from chenodeoxycholate and glycine, usually as the sodium salt. It acts as a detergent to solubilize fats for absorption and is itself absorbed. It is a cholagogue and choleretic.
bile acid glycine conjugatehuman metabolite
1,2-cyclohexanedionecyclohexane-1,2-dione : A cyclohexanedione carrying oxo substituents at positions 1 and 2.

cyclohexanedione : Cyclohexanones carrying two oxo substituents.
cyclohexanedione
4-nitrophenyl acetateC-nitro compound;
phenyl acetates
n-methylisatinN-methylisatin: structure given in first source
9-amino-6-chloro-2-methoxyacridine
acetylacetoneacetylacetone : A beta-diketone that is pentane in which the hydrogens at positions 2 and 4 are replaced by oxo groups.beta-diketone
ursodeoxycholic acidursodeoxycholate : A bile acid anion that is the conjugate base of ursodeoxycholic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.

ursodeoxycholic acid : A bile acid found in the bile of bears (Ursidae) as a conjugate with taurine. Used therapeutically, it prevents the synthesis and absorption of cholesterol and can lead to the dissolution of gallstones.

Ursodeoxycholic Acid: An epimer of chenodeoxycholic acid. It is a mammalian bile acid found first in the bear and is apparently either a precursor or a product of chenodeoxycholate. Its administration changes the composition of bile and may dissolve gallstones. It is used as a cholagogue and choleretic.
bile acid;
C24-steroid;
dihydroxy-5beta-cholanic acid
human metabolite;
mouse metabolite
5-Methoxyisatinindolesanticoronaviral agent
staurosporineindolocarbazole alkaloid;
organic heterooctacyclic compound
apoptosis inducer;
bacterial metabolite;
EC 2.7.11.13 (protein kinase C) inhibitor;
geroprotector
quinaprilquinapril : A member of the class of isoquinolines that is (3S)-2-L-alanyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid in which the alpha-amino group of the alanyl residue has been substituted by a 1-ethoxycarbonyl-4-phenylbutan-2-yl group (the all-S isomer). A prodrug for quinaprilat (by hydrolysis of the ethyl ester to the corresponding carboxylic acid), it is used as an angiotensin-converting enzyme inhibitor (ACE inhibitor) used (generally as the hydrochloride salt) for the treatment of hypertension and congestive heart failure.

Quinapril: A tetrahydroisoquinoline derivative and ANGIOTENSIN CONVERTING ENZYME inhibitor that is used in the treatment of HYPERTENSION and HEART FAILURE.
dicarboxylic acid monoester;
ethyl ester;
isoquinolines;
tertiary carboxamide
antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor;
prodrug
cilazapril, anhydrouscilazapril : A pyridazinodiazepine resulting from the formal condensation of the carboxy group of cilazaprilat with ethanol. It is a drug used in the treatment of hypertension and heart failure.

Cilazapril: One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors) used for hypertension. It is a prodrug that is hydrolyzed after absorption to its main metabolite cilazaprilat.
dicarboxylic acid monoester;
ethyl ester;
pyridazinodiazepine
antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor;
prodrug
clopidogrelclopidogrel : A thienopyridine that is 4,5,6,7-tetrahydrothieno[3,2-c]pyridine in which the hydrogen attached to the nitrogen is replaced by an o-chlorobenzyl group, the methylene hydrogen of which is replaced by a methoxycarbonyl group (the S enantiomer). A P2Y12 receptor antagonist, it is used to inhibit blood clots and prevent heart attacks.

Clopidogrel: A ticlopidine analog and platelet purinergic P2Y receptor antagonist that inhibits adenosine diphosphate-mediated PLATELET AGGREGATION. It is used to prevent THROMBOEMBOLISM in patients with ARTERIAL OCCLUSIVE DISEASES; MYOCARDIAL INFARCTION; STROKE; or ATRIAL FIBRILLATION.
methyl ester;
monochlorobenzenes;
thienopyridine
anticoagulant;
P2Y12 receptor antagonist;
platelet aggregation inhibitor
irinotecancarbamate ester;
delta-lactone;
N-acylpiperidine;
pyranoindolizinoquinoline;
ring assembly;
tertiary alcohol;
tertiary amino compound
antineoplastic agent;
apoptosis inducer;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
prodrug
capecitabinecapecitabine : A carbamate ester that is cytidine in which the hydrogen at position 5 is replaced by fluorine and in which the amino group attached to position 4 is converted into its N-(penyloxy)carbonyl derivative. Capecitabine is a antineoplastic agent used in the treatment of cancers.

Capecitabine: A deoxycytidine derivative and fluorouracil PRODRUG that is used as an ANTINEOPLASTIC ANTIMETABOLITE in the treatment of COLON CANCER; BREAST CANCER and GASTRIC CANCER.
carbamate ester;
cytidines;
organofluorine compound
antimetabolite;
antineoplastic agent;
prodrug
adenosinequinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlitadenosines;
purines D-ribonucleoside
analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
3-methyl-1,2-cyclopentanedione3-methyl-1,2-cyclopentanedione: a peroxynitrite scavenger isolated from coffee extract; structure in first sourcecyclic ketone
ursolic acidhydroxy monocarboxylic acid;
pentacyclic triterpenoid
geroprotector;
plant metabolite
oseltamiviroseltamivir : A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.

Oseltamivir: An acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits NEURAMINIDASE.
acetamides;
amino acid ester;
cyclohexenecarboxylate ester;
primary amino compound
antiviral drug;
EC 3.2.1.18 (exo-alpha-sialidase) inhibitor;
environmental contaminant;
prodrug;
xenobiotic
toxoflavintoxoflavin : A pyrimidotriazine that is 1,6-dimethyl-1,5,6,7-tetrahydropyrimido[5,4-e][1,2,4]triazine with oxo groups at positions 5 and 7.

toxoflavin: azapteridine antibiotic; structure
carbonyl compound;
pyrimidotriazine
antibacterial agent;
antineoplastic agent;
apoptosis inducer;
bacterial metabolite;
toxin;
virulence factor;
Wnt signalling inhibitor
alpha-furilalpha-furil: structure in first source
4-benzoylbenzoic acid4-carboxybenzophenone: a photosensitizer agent
1,10-phenanthroline-5,6-dione1,10-phenanthroline-5,6-dione: has antineoplastic, intercalating, and trypanocidal activities; structure given in first source
2-chloranil
4-nitrophenyl butyratep-nitrophenyl butyrate : A butyrate ester resulting from the formal condensation of the hydroxy group of 4-nitrophenol with the carboxy group of butyric acid.butyrate ester;
C-nitro compound
3,5-di-tert-butyl-1,2-benzoquinone
gamma-glutamine-4-nitroanilidegamma-glutamine-4-nitroanilide: substrate for glutaminase B.; RN given refers to (L)-isomer
5-Chloro-1H-indole-2,3-dioneindolesanticoronaviral agent
5-iodoisatin5-iodoisatin: structure in first sourceindolesanticoronaviral agent
2,2-dimethoxy-2-phenylacetophenone
anisoin
hydrobenzoinhydrobenzoin: structure in first sourceethanediol
fulvestrantfulvestrant : A 3-hydroxy steroid that is 17beta-estradiol in which the 7alpha hydrogen has been replaced by a nonyl group in which one of the hydrogens of the terminal methyl has been replaced by a (4,4,5,5,5-pentafluoropentyl)sulfinyl group. An estrogen receptor antagonist, it is used in the treatment of breast cancer.

Fulvestrant: An estradiol derivative and estrogen receptor antagonist that is used for the treatment of estrogen receptor-positive, locally advanced or metastatic breast cancer.
17beta-hydroxy steroid;
3-hydroxy steroid;
organofluorine compound;
sulfoxide
antineoplastic agent;
estrogen antagonist;
estrogen receptor antagonist
6-hydroxydopa6-hydroxydopa: RN given refers to cpd without isomeric designationnon-proteinogenic alpha-amino acid
tanshinonetanshinone: from root of Salvia miltiorrhiza Bunge; RN given refers to tanshinone I; cardioprotective agent and neuroprotective agentabietane diterpenoidanticoronaviral agent
ly 255283LY 255283: structure given in UD; leukotriene B4 antagonistaromatic ketone
san 58035
1,3-indandione1,2-indanedione: use for detection of latent fingerprints on porous surfaces; structure in first source
gefitinibaromatic ether;
monochlorobenzenes;
monofluorobenzenes;
morpholines;
quinazolines;
secondary amino compound;
tertiary amino compound
antineoplastic agent;
epidermal growth factor receptor antagonist
lestaurtinibindolocarbazole
3-octylthio-1,1,1-trifluoro-2-propanone3-octylthio-1,1,1-trifluoro-2-propanone: a pesticide synergist; inhibits juvenile hormone esterase
vatalanibmonochlorobenzenes;
phthalazines;
pyridines;
secondary amino compound
angiogenesis inhibitor;
antineoplastic agent;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
vascular endothelial growth factor receptor antagonist
ruboxistaurinruboxistaurin: inhibits protein kinase C beta; structure in first source
dexmethylphenidatedexmethylphenidate : A methyl phenyl(piperidin-2-yl)acetate in which both stereocentres have R configuration. It is the active enantiomer in the racemic drug methylphenidate.methyl phenyl(piperidin-2-yl)acetateadrenergic agent
canertinib dihydrochloride
canertinibmonochlorobenzenes;
morpholines;
organofluorine compound;
quinazolines
antineoplastic agent;
tyrosine kinase inhibitor
birb 796aromatic ether;
morpholines;
naphthalenes;
pyrazoles;
ureas
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor;
immunomodulator
miltironemiltirone: from Salvis miltiorrhiza Bunge; central benzodiazepine receptor ligand; structure given in first sourceabietane diterpenoid
cryptotanshinonecryptotanshinone: from Salvia miltiorrhizaabietane diterpenoidanticoronaviral agent
cyc 202seliciclib : 2,6-Diaminopurine carrying benzylamino, (2R)-1-hydroxybutan-2-yl and isopropyl substituents at C-6, C-2-N and N-9 respectively. It is an experimental drug candidate in the family of pharmacological cyclin-dependent kinase (CDK) inhibitors.2,6-diaminopurinesantiviral drug;
EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
ibuprofen acyl glucuronideibuprofen acyl glucuronide: structure given in first source; metabolite of ibuprofen; 13% of ibuprofen administered to humans is excreted in urine as its acyl glucuronideterpene glycoside
tanshinone ii atashinone IIA: a cardiovascular agent with antineoplastic activity; isolated from Salvia miltiorrhiza; structure in first sourceabietane diterpenoid
sb 203580imidazoles;
monofluorobenzenes;
pyridines;
sulfoxide
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor;
geroprotector;
Hsp90 inhibitor;
neuroprotective agent
nbi 27914dialkylarylamine;
tertiary amino compound
enzastaurinindoles;
maleimides
erlotinibaromatic ether;
quinazolines;
secondary amino compound;
terminal acetylenic compound
antineoplastic agent;
epidermal growth factor receptor antagonist;
protein kinase inhibitor
naproxen glucuronidenaproxen glucuronide: structure in first source
lapatinibfurans;
organochlorine compound;
organofluorine compound;
quinazolines
antineoplastic agent;
tyrosine kinase inhibitor
sorafenib(trifluoromethyl)benzenes;
aromatic ether;
monochlorobenzenes;
phenylureas;
pyridinecarboxamide
angiogenesis inhibitor;
anticoronaviral agent;
antineoplastic agent;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
ferroptosis inducer;
tyrosine kinase inhibitor
cholic acidcholic acid : A bile acid that is 5beta-cholan-24-oic acid bearing three alpha-hydroxy substituents at position 3, 7 and 12.

Cholic Acid: A major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.
12alpha-hydroxy steroid;
3alpha-hydroxy steroid;
7alpha-hydroxy steroid;
bile acid;
C24-steroid;
trihydroxy-5beta-cholanic acid
human metabolite;
mouse metabolite
deoxycholic aciddeoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.

Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.
bile acid;
C24-steroid;
dihydroxy-5beta-cholanic acid
human blood serum metabolite
5-Fluoroisatinindolesanticoronaviral agent
lupeolpentacyclic triterpenoid;
secondary alcohol
anti-inflammatory drug;
plant metabolite
paullonepaullone : An indolobenzazepine that is 5,6,7,12-tetrahydroindolo[3,2-d][1]benzazepine carrying an oxo substituent at position 6.

paullone: structure in first source
indolobenzazepine;
lactam
EC 2.7.11.22 (cyclin-dependent kinase) inhibitor;
EC 2.7.11.26 (tau-protein kinase) inhibitor
taurochenodeoxycholic acidtaurochenodeoxycholate : An organosulfonate oxoanion that is the conjugate base of taurochenodeoxycholic acid arising from deprotonation of the sulfonate OH group; major species at pH 7.3.

taurochenodeoxycholic acid : A bile acid taurine conjugate of chenodeoxycholic acid.

Taurochenodeoxycholic Acid: A bile salt formed in the liver by conjugation of chenodeoxycholate with taurine, usually as the sodium salt. It acts as detergent to solubilize fats in the small intestine and is itself absorbed. It is used as a cholagogue and choleretic.
bile acid taurine conjugatehuman metabolite;
mouse metabolite
hyperforinhyperforin : A cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, Hypericum perforatum.

hyperforin: a prenylated acylphloroglucinol derivative; antibiotic component of novoimanine; psychoactive agent in St. John's wort; Russian; structure;
surfactin csurfactin C : A cyclodepsipeptide that is N-[(3R)-3-hydroxy-13-methyltetradecanoyl]-L-alpha-glutamyl-L-leucyl-D-leucyl-L-valyl-L-alpha-aspartyl-D-leucyl-L-leucine in which the C-terminal carboxy group has been lactonised by condensation with the alcoholic hydroxy group.cyclodepsipeptide;
lipopeptide antibiotic;
macrocyclic lactone
antibacterial agent;
antifungal agent;
antineoplastic agent;
antiviral agent;
metabolite;
platelet aggregation inhibitor;
surfactant
temocaprildipeptide
resveratroltrans-resveratrol : A resveratrol in which the double bond has E configuration.resveratrolantioxidant;
phytoalexin;
plant metabolite;
quorum sensing inhibitor;
radical scavenger
cocainecocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.

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.
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
5,11-diethyl-5,6,11,12-tetrahydrochrysene-2,8-diol(R,R)-5,11-diethyl-5,6,11,12-tetrahydro-2,8-chrysenediol : A carbotetracyclic compound that is 5,6,11,12-tetrahydrochrysene substituted by hydroxy groups at positions 2 and 8 and by ethyl groups at positions 5 and 11 (the 5R,11R-stereoisomer). It is an agonist of ER-alpha and antagonist of ER-beta receptors.

5,11-diethyl-5,6,11,12-tetrahydrochrysene-2,8-diol: estrogen receptor ligand; structure in first source
carbotetracyclic compound;
polyphenol
estrogen receptor agonist;
estrogen receptor antagonist;
geroprotector;
neuroprotective agent
pd 173955PD 173955: inhibits src family-selective tyrosine kinase; structure in first sourcearyl sulfide;
dichlorobenzene;
methyl sulfide;
pyridopyrimidine
tyrosine kinase inhibitor
obeticholic acidobeticholic acid : A dihydroxy-5beta-cholanic acid that is chenodeoxycholic acid carrying an additional ethyl substituent at the 6alpha-position. A semi-synthetic bile acid which acts as a farnesoid X receptor agonist and is used for treatment of primary biliary cholangitis.

obeticholic acid: A farnesoid X receptor agonist and anticholestatic agent that is used in the treatment of chronic liver diseases; structure in first source.
3alpha-hydroxy steroid;
7alpha-hydroxy steroid;
dihydroxy-5beta-cholanic acid
farnesoid X receptor agonist;
hepatoprotective agent
t0901317T0901317: an LXRalpha and LXRbeta agonist
6-bromoindirubin-3'-oxime6-bromoindirubin-3'-oxime : A member of the class of biindoles that is indirubin substituted at position 6 by a bromo group and in which the keto group at position 3' has undergone condensation with hydroxylamine to form the corresponding oxime.

6-bromoindirubin-3'-oxime: structure in first source
s 1033(trifluoromethyl)benzenes;
imidazoles;
pyridines;
pyrimidines;
secondary amino compound;
secondary carboxamide
anticoronaviral agent;
antineoplastic agent;
tyrosine kinase inhibitor
CHIC-35CHIC-35 : An organic heterotricyclic compound resulting from the formal fusion of the 2-3 bond of 5-chloroindole with the 2-3 bond of cycloheptanecarboxamide (the S enantiomer). It is a potent, cell-permeable, metabolically stable and selective inhibitor of the deacetylase SIRT1.aromatic compound;
organic heterotricyclic compound;
organochlorine compound;
primary carboxamide
EC 3.5.1.98 (histone deacetylase) inhibitor
3-(1-azepanylsulfonyl)-n-(3-bromphenyl)benzamide3-(1-azepanylsulfonyl)-N-(3-bromphenyl)benzamide: a sirtuin 2 inhibitor; structure in first source
CAY10591CAY10591: a SIRT1 NAD-dependent histone deacetylase activatorquinoxaline derivative
1-[(3,4-dichlorophenyl)methyl]indole-2,3-dioneindoles
sirtinolaldimine;
benzamides;
naphthols
anti-inflammatory agent;
EC 3.5.1.98 (histone deacetylase) inhibitor;
Sir2 inhibitor
bms 387032N-(5-(((5-(1,1-dimethylethyl)-2-oxazolyl)methyl)thio)-2-thiazolyl)-4-piperidinecarboxamide: a CDK2 inhibitor with antineoplastic activity; structure in first source

N-(5-{[(5-tert-butyl-1,3-oxazol-2-yl)methyl]sulfanyl}-1,3-thiazol-2-yl)piperidine-4-carboxamide : A secondary carboxamide resulting from the formal condensation of the carboxy group of piperidine-4-carboxylic acid with the amino group of 5-{[(5-tert-butyl-1,3-oxazol-2-yl)methyl]sulfanyl}-1,3-thiazol-2-amine. It is an ATP-competitive inhibitor of CDK2, CDK7 and CDK9 kinases and exhibits anti-cancer properties.
1,3-oxazoles;
1,3-thiazoles;
organic sulfide;
piperidinecarboxamide;
secondary carboxamide
angiogenesis inhibitor;
antineoplastic agent;
apoptosis inducer;
EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
tandutinibaromatic ether;
N-arylpiperazine;
N-carbamoylpiperazine;
phenylureas;
piperidines;
quinazolines;
tertiary amino compound
antineoplastic agent;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor
vx-745aryl sulfide;
dichlorobenzene;
difluorobenzene;
pyrimidopyridazine
anti-inflammatory drug;
apoptosis inducer;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
dasatinibdasatinib (anhydrous) : An aminopyrimidine that is 2-methylpyrimidine which is substituted at position 4 by the primary amino group of 2-amino-1,3-thiazole-5-carboxylic acid and at position 6 by a 4-(2-hydroxyethyl)piperazin-1-yl group, and in which the carboxylic acid group has been formally condensed with 2-chloro-6-methylaniline to afford the corresponding amide. A multi-targeted kinase inhibitor, it is used, particularly as the monohydrate, for the treatment of chronic, accelerated, or myeloid or lymphoid blast phase chronic myeloid leukemia. Note that the name 'dasatinib' is used to refer to the monohydrate (USAN) as well as to anhydrous dasatinib (INN).

N-(2-chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)-1,3-thiazole-5-carboxamide: a dasatinib prodrug; structure in first source
1,3-thiazoles;
aminopyrimidine;
monocarboxylic acid amide;
N-(2-hydroxyethyl)piperazine;
N-arylpiperazine;
organochlorine compound;
secondary amino compound;
tertiary amino compound
anticoronaviral agent;
antineoplastic agent;
tyrosine kinase inhibitor
zd 6474CH 331: structure in first sourcearomatic ether;
organobromine compound;
organofluorine compound;
piperidines;
quinazolines;
secondary amine
antineoplastic agent;
tyrosine kinase inhibitor
cambinolcambinol: inhibitor of human silent information regulator 2 enzymes; structure in first source
gw 7647GW 7647 : A monocarboxylic acid that is 2-(phenylsulfanyl)isobutyric acid in which the phenyl group is substituted at the para- position by a 3-aza-7-cyclohexylhept-1-yl group in which the nitrogen is acylated by a (cyclohexylamino)carbonyl group.

GW 7647: a PPAR-alpha agonist; structure in first source
aryl sulfide;
monocarboxylic acid;
ureas
PPARalpha agonist
(4-chlorophenyl)-[4-(8-nitro-5-quinolinyl)-1-piperazinyl]methanoneN-arylpiperazine
jhw 015indolecarboxamide
pd 407824
4-(5-benzo(1,3)dioxol-5-yl-4-pyridin-2-yl-1h-imidazol-2-yl)benzamide4-(5-benzo(1,3)dioxol-5-yl-4-pyridin-2-yl-1H-imidazol-2-yl)benzamide: a TGF-beta type I receptor kinase activity inhibitorbenzamides;
benzodioxoles;
imidazoles;
pyridines
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor
5-Nitroisatinindolesanticoronaviral agent
ex 5276-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide : A member of the class of carbazoles that is 2,3,4,9-tetrahydro-1H-carbazole which is substituted at position 1 by an aminocarbohyl group and at position 6 by a chlorine.

6-chloro-2,3,4,9-tetrahydro-1H-carbazole-1-carboxamide: structure in first source
carbazoles;
monocarboxylic acid amide;
organochlorine compound
alvocidibalvocidib : A synthetic dihydroxyflavone that is 5,7-dihydroxyflavone which is substituted by a 3-hydroxy-1-methylpiperidin-4-yl group at position 8 and by a chlorine at the 2' position (the (-)-3S,4R stereoisomer). A cyclin-dependent kinase 9 (CDK9) inhibitor, it has been studied for the treatment of acute myeloid leukaemia, arthritis and atherosclerotic plaque formation.

alvocidib: structure given in first source
dihydroxyflavone;
hydroxypiperidine;
monochlorobenzenes;
tertiary amino compound
antineoplastic agent;
antirheumatic drug;
apoptosis inducer;
EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
pd 166285
andrographolidecarbobicyclic compound;
gamma-lactone;
labdane diterpenoid;
primary alcohol;
secondary alcohol
anti-HIV agent;
anti-inflammatory drug;
antineoplastic agent;
metabolite
fexaraminefexaramine: structure in first sourcebiphenyls
pd 089828PD 089828: structure in first source
pd 166866PD 166866: structure in first source

PD-166866 : A member of the class of pyridopyrimidines that is pyrido[2,3-d]pyrimidine substituted by an amino group at position 2, 3,5-dimethoxyphenyl group at position 6, and by a (tert-butylcarbamoyl)nitrilo group at position 7. It is a selective ATP competitive inhibitor of the human fibroblast growth factor-1 receptor (FGFR1) tyrosine kinase with an IC50 of 52.4 nM.
biaryl;
dimethoxybenzene;
primary arylamine;
pyridopyrimidine;
ureas
angiogenesis inhibitor;
antineoplastic agent;
apoptosis inducer;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor
pd 161570PD 161570: structure in first source
bosutinib4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(4-methyl-1-piperazinyl)propoxy)-3-quinolinecarbonitrile: a Src kinase inhibitor; structure in first sourceaminoquinoline;
aromatic ether;
dichlorobenzene;
N-methylpiperazine;
nitrile;
tertiary amino compound
antineoplastic agent;
tyrosine kinase inhibitor
semaxinibsemaxanib : An oxindole that is 3-methyleneoxindole in which one of the hydrogens of the methylene group is replaced by a 3,5-dimethylpyrrol-2-yl group.olefinic compound;
oxindoles;
pyrroles
angiogenesis modulating agent;
antineoplastic agent;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
vascular endothelial growth factor receptor antagonist
su 11248monocarboxylic acid amide;
pyrroles
angiogenesis inhibitor;
antineoplastic agent;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
immunomodulator;
neuroprotective agent;
vascular endothelial growth factor receptor antagonist
pd 0183812PD 0183812: inhibits CDK4 and CDK6; structure in first source
jnj-7706621sulfonamide
delaprildelapril: RN refers to HCl; structure given in first sourcepeptide
benazeprilbenazepril : A benzazepine that is benazeprilat in which the carboxy group of the 2-amino-4-phenylbutanoic acid moiety has been converted to the corresponding ethyl ester. It is used (generally as its hydrochloride salt) as a prodrug for the angiotensin-converting enzyme inhibitor benazeprilat in the treatment of hypertension and heart failure.

benazepril: structure given in first source
benzazepine;
dicarboxylic acid monoester;
ethyl ester;
lactam
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor;
prodrug
heroinheroin : A morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses.

Heroin: A narcotic analgesic that may be habit-forming. It is a controlled substance (opium derivative) listed in the U.S. Code of Federal Regulations, Title 21 Parts 329.1, 1308.11 (1987). Sale is forbidden in the United States by Federal statute. (Merck Index, 11th ed)
morphinane alkaloidmu-opioid receptor agonist;
opioid analgesic;
prodrug
6-o-monoacetylmorphine6-O-monoacetylmorphine: RN given refers to parent cpd(5alpha,6alpha)-isomermorphinane alkaloid
imidaprilimidapril : A member of the class of imidazolidines that is (4S)-1-methyl-2-oxoimidazolidine-4-carboxylic acid in which the hydrogen of the imidazolidine nitrogen has been substituted by (1S)-1-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}ethyl group. It is the prodrug for imidaprilat, an ACE inhibitor used for the treatment of chronic heart failure.

imidapril: structure given in first source
dicarboxylic acid monoester;
dipeptide;
ethyl ester;
imidazolidines;
N-acylurea;
secondary amino compound
antihypertensive agent;
EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor;
prodrug
2-tert-butyl-9-fluoro-3,6-dihydro-7h-benz(h)imidazo(4,5-f)isoquinoline-7-one2-tert-butyl-9-fluoro-1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one : An organic heterotetracyclic compound that is 1,6-dihydrobenzo[h]imidazo[4,5-f]isoquinolin-7-one bearing additional tert-butyl and fluoro substituents at positions 2 and 9 respectively.

2-tert-butyl-9-fluoro-3,6-dihydro-7H-benz(h)imidazo(4,5-f)isoquinoline-7-one: a janus-activated kinase inhibitor
organic heterotetracyclic compound;
organofluorine compound
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
vx680N-arylpiperazine
pregna-4,17-diene-3,16-dionepregna-4,17-diene-3,16-dione: steroid from guggulu extract; RN & N1 from C1 Form index; RN given refers to cpd without isomeric designation; structure in first source; antagonist of farnesoid X receptor3-hydroxy steroidandrogen
ekb 569EKB 569: an EGF receptor kinase inhibitoraminoquinoline;
monocarboxylic acid amide;
monochlorobenzenes;
nitrile
protein kinase inhibitor
pregna-4,17-diene-3,16-dione, (17z)-isomer
axitinibaryl sulfide;
benzamides;
indazoles;
pyridines
antineoplastic agent;
tyrosine kinase inhibitor;
vascular endothelial growth factor receptor antagonist
gdp 366GDP 366: an antineoplastic agent; structure in first source
pd 1843522-(2-chloro-4-iodophenylamino)-N-cyclopropylmethoxy-3,4-difluorobenzamide: inhibits MAP kinase kinase; structure in first sourceaminobenzoic acid
panobinostatpanobinostat : A hydroxamic acid obtained by formal condensation of the carboxy group of (2E)-3-[4-({[2-(2-methylindol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enoic acid with the amino group of hydroxylamine. A histone deacetylase inhibitor used (as its lactate salt) in combination with bortezomib and dexamethasone for the treatment of multiple myeloma.

Panobinostat: An indole and hydroxamic acid derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used as an antineoplastic agent in combination with BORTEZOMIB and DEXAMETHASONE for the treatment of MULTIPLE MYELOMA.
cinnamamides;
hydroxamic acid;
methylindole;
secondary amino compound
angiogenesis modulating agent;
antineoplastic agent;
EC 3.5.1.98 (histone deacetylase) inhibitor
bms3455414(2'-aminoethyl)amino-1,8-dimethylimidazo(1,2-a)quinoxaline: structure in first sourcequinoxaline derivative
midostaurinmidostaurin : An organic heterooctacyclic compound that is the N-benzoyl derivative of staurosporine.benzamides;
gamma-lactam;
indolocarbazole;
organic heterooctacyclic compound
antineoplastic agent;
EC 2.7.11.13 (protein kinase C) inhibitor
ki 20227
cp 7247142-methoxy-N-(3-(4-((3-methyl-4-((6-methyl-3-pyridinyl)oxy)phenyl)amino)-6-quinazolinyl)-2-propenyl)acetamide: CP-724714 is the ((2E)-isomer, 1:1.5 succinate); structure in first source2-methoxy-N-[3-[4-[3-methyl-4-[(6-methyl-3-pyridinyl)oxy]anilino]-6-quinazolinyl]prop-2-enyl]acetamideantineoplastic agent;
apoptosis inducer;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
hepatotoxic agent
pi103PI103: pyridofuropyrimidine antineoplastic; a potent inhibitor of class I phosphatidylinositide 3-kinases (PI3K); structure in first sorucearomatic amine;
morpholines;
organic heterotricyclic compound;
phenols;
tertiary amino compound
antineoplastic agent;
EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor;
mTOR inhibitor
ct52923CT52923: structure in first source
gw 4064stilbenoid
hki 272nitrile;
quinolines
antineoplastic agent;
tyrosine kinase inhibitor
tofacitinibtofacitinib : A pyrrolopyrimidine that is pyrrolo[2,3-d]pyrimidine substituted at position 4 by an N-methyl,N-(1-cyanoacetyl-4-methylpiperidin-3-yl)amino moiety. Used as its citrate salt to treat moderately to severely active rheumatoid arthritis.N-acylpiperidine;
nitrile;
pyrrolopyrimidine;
tertiary amino compound
antirheumatic drug;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
n-(6-chloro-7-methoxy-9h-beta-carbolin-8-yl)-2-methylnicotinamide
cediranibaromatic ether
way-362450indoles
masitinib1,3-thiazoles;
benzamides;
N-alkylpiperazine;
pyridines
antineoplastic agent;
antirheumatic drug;
tyrosine kinase inhibitor
oblongifolin coblongifolin C: has antineoplastic activity; isolated from Garcinia yunnanensis; structure in first source
pazopanibpazopanib : A pyrimidine that is 5-(pyrimidin-2-yl}amino-2-methylbenzenesulfonamide substituted at position 4 by a (2,3-dimethylindazol-6-yl)(methyl)amino group. Used as its hydrochloride salt for treatment of kidney cancer.

pazopanib: a protein kinase inhibitor
aminopyrimidine;
indazoles;
sulfonamide
angiogenesis modulating agent;
antineoplastic agent;
tyrosine kinase inhibitor;
vascular endothelial growth factor receptor antagonist
azd 6244AZD 6244: a MEK inhibitorbenzimidazoles;
bromobenzenes;
hydroxamic acid ester;
monochlorobenzenes;
organofluorine compound;
secondary amino compound
anticoronaviral agent;
antineoplastic agent;
EC 2.7.11.24 (mitogen-activated protein kinase) inhibitor
su 148135-((5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl)-N-(2-hydroxy-3-morpholin-4-ylpropyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide: has both antineoplastic and antiangiogenic activities; structure in first source
bibw 2992aromatic ether;
enamide;
furans;
monochlorobenzenes;
organofluorine compound;
quinazolines;
secondary carboxamide;
tertiary amino compound
antineoplastic agent;
tyrosine kinase inhibitor
12-epi-scalarin12-epi-scalarin : The 12-epimer of scalarin, a metabolite of marine sponges of the genus Spongia.scalarane sesterterpenoidanimal metabolite
ol-135
tg100-1153,3'-(2,4-diaminopteridine-6,7-diyl)diphenol: for treatment of ischemia reperfusion injury; structure in first sourcepteridines
pha 665752dichlorobenzene;
enamide;
indolones;
N-acylpyrrolidine;
pyrrolecarboxamide;
secondary carboxamide;
sulfone;
tertiary carboxamide
antineoplastic agent;
c-Met tyrosine kinase inhibitor
PDGF receptor tyrosine kinase inhibitor IIIPDGF receptor tyrosine kinase inhibitor III : An N-arylpiperazine that is piperazine in which the hydrogen attached to the nitrogen at position 1 is replaced by a (4-phenoxyphenyl)aminocarbonyl group, while the hydrogen attached to the nitrogen at position 4 is replaced by a 6,7-dimethoxyquinazolin-4-yl group. It is an inhibitor of tyrosine kinases FLT3, PDGFR and KIT.aromatic ether;
N-arylpiperazine;
N-carbamoylpiperazine;
phenylureas;
quinazolines;
tertiary amino compound
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor
6-[[5-fluoro-2-(3,4,5-trimethoxyanilino)-4-pyrimidinyl]amino]-2,2-dimethyl-4H-pyrido[3,2-b][1,4]oxazin-3-onemethoxybenzenes;
substituted aniline
brivanibaromatic ether;
diether;
fluoroindole;
pyrrolotriazine;
secondary alcohol
angiogenesis inhibitor;
antineoplastic agent;
apoptosis inducer;
drug metabolite;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
fibroblast growth factor receptor antagonist
at 75194-(2,6-dichlorobenzamido)-N-(piperidin-4-yl)-pyrazole-3-carboxamide : A member of the class of pryrazoles that is 4-amino-1H-pyrazole-3-carboxylic acid in which the primary amino group has been acylated by a 2,6-dichlorobenzoyl group and in which the carboxylic acid has been converted into a carboxamide by formal condensation with the primary amino group of 4-aminopiperidine.dichlorobenzene;
piperidines;
pyrazoles;
secondary carboxamide
antineoplastic agent;
EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
bi 2536
nvp-ast487NVP-AST487: antineoplastic; a RET kinase inhibitor that blocks growth and calcitonin gene expression through distinct mechanisms in medullary thyroid cancer cells
Dihydrotanshinone Idihydrotanshinone I: extracted from Radix Salviaeabietane diterpenoidanticoronaviral agent
kw 2449KW 2449: has both multikinase inhibitory activity and antineoplastic activity; structure in first source
nvp-aew541
abt 869aromatic amine;
indazoles;
phenylureas
angiogenesis inhibitor;
antineoplastic agent;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor
quisinostatindoles
gw 25805-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)pyrimidine-2,4-diamine: a cFMS kinase inhibitor; structure in first source
crizotinibcrizotinib : A 3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)pyrazol-4-yl]pyridin-2-amine that has R configuration at the chiral centre. The active enantiomer, it acts as a kinase inhibitor and is used for the treatment of patients with locally advanced or metastatic non-small cell lung cancer (NSCLC)

Crizotinib: A piperidine and aminopyridine derivative that acts as an inhibitor of RECEPTOR PROTEIN-TYROSINE KINASES, including ANAPLASTIC LYMPHOMA KINASE (ALK) and HEPATOCYTE GROWTH FACTOR RECEPTOR (HGFR; c-Met). It is used in the treatment of NON-SMALL CELL LUNG CANCER.
3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)pyrazol-4-yl]pyridin-2-amineantineoplastic agent;
biomarker;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor
chir-265aromatic ether
motesanibpyridinecarboxamide
mln8054benzazepine
GDC-0879indanes;
ketoxime;
primary alcohol;
pyrazoles;
pyridines
antineoplastic agent;
B-Raf inhibitor
glycoursodeoxycholic acidglycoursodeoxycholate : A N-acylglycinate that is the conjugate base of glycoursodeoxycholic acid. obtained by deprotonation of the carboxy group; major species at pH 7.3.

glycoursodeoxycholic acid : A bile acid glycine conjugate derived from ursoodeoxycholic acid.
bile acid glycine conjugate;
N-acylglycine
human blood serum metabolite;
neuroprotective agent
alisol b monoacetatealisol B 23-acetate: from Alisma orientale rhizome; structure in first sourcetriterpenoid
alisol c 23-acetatealisol C 23-acetate: isolated from Alismatis Rhizoma; structure in first source
alisol aalisol A: has anti-hepatitis B virus activity; structure
alisol btriterpenoid
gsk 461364GSK 461364: an antineoplastic agent that inhibits polo-like kinase 1(trifluoromethyl)benzenes
azd 1152-hqpaAZD2811: has antineoplastic activity; structure in first sourceanilide;
monofluorobenzenes;
primary alcohol;
pyrazoles;
quinazolines;
secondary amino compound;
secondary carboxamide;
tertiary amino compound
antineoplastic agent;
Aurora kinase inhibitor
nvp-tae684piperidines
archazolid aarchazolid A: inhibits vacuolar-type ATPase; isolated from Archangium gephyra; structure in first source
fedratinibfedratinib: a selective small-molecule inhibitor of JAK2sulfonamide
gsk6906931,2,5-oxadiazole;
acetylenic compound;
aromatic amine;
aromatic ether;
imidazopyridine;
piperidines;
primary amino compound;
tertiary alcohol
antineoplastic agent;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor
t-tucb
gdc 0941pictrelisib : A sulfonamide composed of indazole, morpholine, and methylsulfonyl-substituted piperazine rings bound to a thienopyrimidine ring.indazoles;
morpholines;
piperazines;
sulfonamide;
thienopyrimidine
EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor
23-hydroxybetulinic acid23-hydroxybetulinic acid: structure in first sourcetriterpenoidmetabolite
tanshinone ii a sodium sulfonatetanshinone II A sodium sulfonate: has cardioprotective activity; water-soluble derivative of tanshinone II A; isolated from Salvia militiorrhiza; relieves anginal pain; structure
srt1460SRT1460: small molecule activator of SIRT1 as therapeutics for the treatment of type 2 diabetes; structure in first source
srt1720
srt2183SRT2183: small molecule activator of SIRT1 as therapeutics for the treatment of type 2 diabetes; structure in first source
plx 4720PLX 4720: a B-Raf(V600E) kinase inhibitor; structure in first sourcearomatic ketone;
difluorobenzene;
organochlorine compound;
pyrrolopyridine;
sulfonamide
antineoplastic agent;
B-Raf inhibitor
tenovin-6tenovin-6 : A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-(dimethylamino)pentanoic acid with the aromatic amino group of N-[(4-aminophenyl)carbamothioyl]-4-tert-butylbenzamide.monocarboxylic acid amide;
tertiary amino compound;
thioureas
antineoplastic agent;
p53 activator;
Sir2 inhibitor
sgx 523aryl sulfide;
biaryl;
pyrazoles;
quinolines;
triazolopyridazine
c-Met tyrosine kinase inhibitor;
nephrotoxic agent
ponatinib(trifluoromethyl)benzenes;
acetylenic compound;
benzamides;
imidazopyridazine;
N-methylpiperazine
antineoplastic agent;
tyrosine kinase inhibitor
quizartinibbenzoimidazothiazole;
isoxazoles;
morpholines;
phenylureas
antineoplastic agent;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor;
necroptosis inhibitor
incb-018424nitrile;
pyrazoles;
pyrrolopyrimidine
antineoplastic agent;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
gsk 1838705aorganonitrogen compound;
organooxygen compound
gsk 1363089GSK 1363089: a multikinase inhibitor that acts on Met, RON, Axl, and VEGFR; structure in first sourcearomatic ether
int-777
ly2874455
azd4547benzamides;
N-arylpiperazine;
pyrazoles
fibroblast growth factor receptor antagonist
3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-(6-(4-(4-ethylpiperazin-1-yl)-phenylamino)pyrimidin-4-yl)-1-methylureaBGJ-398 : A member of the class of phenylureas that is urea in which a hydrogen attached to one of the nitrogens is replaced by a 2,6-dichloro-3,5-dimethoxyphenyl group, while the hydrogens attached to the other nitrogen are replaced by a methyl group and a 6-{[4-(4-ethylpiperazin-1-yl)phenyl]amino}pyrimidin-4-yl group. It is a potent and selective fibroblast growth factor receptor inhibitor.

infigratinib: structure in first source
aminopyrimidine;
dichlorobenzene;
N-alkylpiperazine;
N-arylpiperazine;
phenylureas
antineoplastic agent;
fibroblast growth factor receptor antagonist
acy-1215ricolinostat: an HDAC6 inhibitor; structure in first sourcepyrimidinecarboxylic acid
ceritinibceritinib : A member of the class of aminopyrimidines that is 2,6-diamino-5-chloropyrimidine in which the amino groups at positions 2 and 6 are respectively carrying 2-methoxy-4-(piperidin-4-yl)-5-methylphenyl and 2-(isopropylsulfonyl)phenyl substituents. Used for the treatment of ALK-positive metastatic non-small cell lung cancer.

ceritinib: an anaplastic lymphoma kinase inhibitor
aminopyrimidine;
aromatic ether;
organochlorine compound;
piperidines;
secondary amino compound;
sulfone
antineoplastic agent;
EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor
debio 1347CH5183284: a fibroblast growth factor receptor antagonist; structure in first source
pf-543PF-543: Sphingosine Kinase 1 Selective Inhibitor; structure in first sourcesulfonamide
erdafitiniberdafitinib: inhibitor of fibroblast growth factor receptors
alisol f
alisol a 24-acetatealisol A 24-acetate: isolated from Alismatis Rhizoma; structure in first source
aristoforinAristoforin: derivative of hyperforin, is a potent anticancer agent; structure in first source
4-(2-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolyl)methoxy)phenyl)cyclopropyl)benzoic acid4-(2-(2-chloro-4-((5-cyclopropyl-3-(2,6-dichlorophenyl)-4-isoxazolyl)methoxy)phenyl)cyclopropyl)benzoic acid: a farnesoid X receptor agonist; structure in first source
chir 258
nintedanibnintedanib : A member of the class of oxindoles that is a kinase inhibitor used (in the form of its ethylsulfonate salt) for the treatment of idiopathic pulmonary fibrosis and cancer.
pp242torkinib : A member of the class of pyrazolopyrimidines that is 1H-pyrazolo[3,4-d]pyrimidine substituted by isopropyl, 5-hydroxyindol-2-yl and amino groups at positions 1, 3 and 4 respectively. It is a potent inhibitor of mTOR and exhibits anti-cancer properties.aromatic amine;
biaryl;
hydroxyindoles;
phenols;
primary amino compound;
pyrazolopyrimidine
antineoplastic agent;
mTOR inhibitor
n-(3-((2-hydroxynaphthalen-1-ylmethylene)amino)phenyl)-2-phenylpropionamide