Chemical Entities of Biological Interest (ChEBI) (original) (raw)
The recent refurbishment of the Shared Facilities Building of our Hinxton campus has included the installation of a series of cladding panels in the refreshment facilities, made up of around 500 perforated metal plates depicting around 70 molecules. These were selected from a short list choosen by the ChEBI team and rendered in 3-Dimensional form by John May, a PhD student in Chemoinformatics and Metabolism team at EBI.
Amphetamine (contracted from alpha-methylphenethylamine) is a potent central nervous system (CNS) stimulant of the phenethylamine class that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. ... more
Auranofin is a gold complex classified by the World Health Organization as an antirheumatic agent. It has the brand name Ridaura. ... more
Capsaicin (8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is an irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. ... more
Chloroquine is a 4-aminoquinoline drug used in the treatment or prevention of malaria. ... more
Curcumin (pronounced "Kur kyoo min") is a diarylheptanoid. It is the principal curcuminoid of the popular South Asian spice turmeric, which is a member of the ginger family (Zingiberaceae). Turmeric's other two curcuminoids are desmethoxycurcumin and bis-desmethoxycurcumin. ... more
Glucose (also known as dextrose, or grape sugar) is a simple aldosic monosaccharide found in plants. It is a monosaccharide that is absorbed directly into the bloodstream during digestion. It is an important carbohydrate in biology, which is indicated by the fact that cells use it as a secondary source of energy and a metabolic intermediate. ... more
Ibuprofen (INN, BAN, AAN and USAN) (from isobutylphenylpropanoic acid) is a nonsteroidal anti-inflammatory drug (NSAID) derivative of propionic acid used for relieving pain, helping with fever and reducing inflammation. ... more
Oseltamivir INN, marketed under the trade name Tamiflu, is an antiviral licensed to prevent or slow the spread of influenza A and influenza B (flu) virus between cells in the body by stopping the virus from chemically cutting ties with its host cell. ... more
Porphyrins are a group of heterocyclic macrocycle organic compounds, composed of four modified pyrrole subunits interconnected at their α carbon atoms via methine bridges (=CH-). The parent porphyrin is porphine, and substituted porphines are called porphyrins. ... more
Thalidomide (from phthalimido-glutarimide. Currently marketed under the brand names Immunoprin, Talidex, Talizer, Thalomid) is an immunomodulatory drug and the prototype of the thalidomide class of drugs. It was first marketed in 1957 in West Germany under the trade-name Contergan. ... more
thiopental sodium (CHEBI:9561)
Sodium thiopental, also known as Sodium Pentothal (a trademark of Abbott Laboratories), thiopental, thiopentone, or Trapanal (also a trademark), is a rapid-onset short-acting barbiturate general anesthetic that is an analogue of thiobarbital. Sodium thiopental is a core medicine in the World Health Organization's "Essential Drugs List", which is a list of minimum medical needs for a basic healthcare system. ... more
Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. All genomes sequenced to date encode enzymes that use coenzyme A as a substrate, and around 4% of cellular enzymes use it (or a thioester, such as acetyl-CoA) as a substrate. ... more
Acetylcholine (ACh, pron. ah-Seh-til-KO-leen) is an organic molecule that acts as a neurotransmitter in many organisms, including humans. It is an ester of acetic acid and choline, with chemical formula CH3COO(CH2)2N+(CH3)3 and systematic name 2-acetoxy-N,N,N-trimethylethanaminium. ... more
acetylsalicylic acid (CHEBI:15365)
Aspirin (BAN, USAN), also known as acetylsalicylic acid [ASA], is a salicylate drug, often used as an analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an anti-inflammatory medication. ... more
Menthol is an organic compound made synthetically or obtained from cornmint, peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (-)-menthol, which is assigned the (1R,2S,5R) configuration. ... more
Adenosine triphosphate (ATP) is a nucleoside triphosphate used in cells as a coenzyme, often called the "molecular unit of currency" of intracellular energy transfer. ATP transports chemical energy within cells for metabolism. It is one of the end products of photophosphorylation, cellular respiration, and fermentation and used by enzymes and structural proteins in many cellular processes, including biosynthetic reactions, motility, and cell division. ... more
Cephalosporin C is an antibiotic of the cephalosporin class. It was isolated from fungi of the genus Acremonium and first characterized in 1961. Although not a very active antibiotic itself, synthetic analogs of cephalosporin C, such as cefalotin, became some of the first marketed cephalosporin antibiotic drugs. ... more
Quinine (KWIN-een) is a natural white crystalline alkaloid having antipyretic (fever-reducing), antimalarial, analgesic (painkilling), and anti-inflammatory properties and a bitter taste. It is a stereoisomer of quinidine, which, unlike quinine, is an antiarrhythmic. ... more
Glutamic acid (abbreviated as Glu or E) is one of the 20-23 proteinogenic amino acids, and its codons are GAA and GAG. It is a non-essential amino acid. The carboxylate anions and salts of glutamic acid are known as glutamates. In neuroscience, glutamate is an important neurotransmitter that plays the principal role in neural activation. ... more
Cytosine (C) is one of the four main bases found in DNA and RNA, along with adenine, guanine, and thymine (uracil in RNA). It is a pyrimidine derivative, with a heterocyclic aromatic ring and two substituents attached (an amine group at position 4 and a keto group at position 2). ... more
Cholesterol, from the Ancient Greek chole- (bile) and stereos (solid) followed by the chemical suffix -ol for an alcohol, is an organic molecule. It is a sterol (or modified steroid), a lipid molecule and is biosynthesized by many animal cells because it is an essential structural component of animal cell membranes that is required to maintain both membrane structural integrity and fluidity. ... more
DDT ("dichlorodiphenyltrichloroethane") is a colorless, crystalline, tasteless and almost odorless organochloride known for its insecticidal properties. DDT has been formulated in almost every conceivable form, including solutions in xylene or petroleum distillates, emulsifiable concentrates, water-wettable powders, granules, aerosols, smoke candles and charges for vaporizers and lotions. ... more
Guanine (G, Gua) is one of the four main nucleobases found in the nucleic acids DNA and RNA, the others being adenine, cytosine, and thymine (uracil in RNA). In DNA, guanine is paired with cytosine. With the formula C5H5N5O, guanine is a derivative of purine, consisting of a fused pyrimidine-imidazole ring system with conjugated double bonds. ... more
Naphthalene is an organic compound with formula C 10H 8. It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. ... more
Adenine (A, Ade) is a nucleobase (a purine derivative) with a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD), and protein synthesis, as a chemical component of DNA and RNA. ... more
γ-aminobutyric acid (CHEBI:16865)
γ-Aminobutyric acid (GABA) is the chief inhibitory neurotransmitter in the mammalian central nervous system. It plays the principal role in reducing neuronal excitability throughout the nervous system. In humans, GABA is also directly responsible for the regulation of muscle tone. ... more
Nicotinamide adenine dinucleotide (NAD) is a coenzyme found in all living cells. The compound is a dinucleotide, because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an adenine base and the other nicotinamide. ... more
Alanine (abbreviated as Ala or A) is an α-amino acid with the chemical formula CH3CH(NH2)COOH. The L-isomer is one of the 20 amino acids encoded by the genetic code. Its codons are GCU, GCC, GCA, and GCG. It is classified as a non-polar amino acid. L-Alanine is second only to leucine in rate of occurrence, accounting for 7. ... more
Riboflavin (vitamin B2) is part of the vitamin B group. It is central component of the cofactors FAD and FMN and as such required for a variety of flavoprotein enzyme reactions including activation of other vitamins. It was formerly known as vitamin G. ... more
Progesterone (pregn-4-ene-3,20-dione; abbreviated as P4) is an endogenous steroid hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens, and is the major progestogen in the body. ... more
Streptomycin is an antibiotic (antimycobacterial) drug, the first of a class of drugs called aminoglycosides to be discovered, and it was the first cure for tuberculosis. It is derived from the actinobacterium Streptomyces griseus. Streptomycin is a bactericidal antibiotic. ... more
Serine (abbreviated as Ser or S) is an amino acid with the formula HO2CCH(NH2)CH2OH. It is one of the proteinogenic amino acids. Its codons in the genetic code are UCU, UCC, UCA, UCG, AGU and AGC. By virtue of the hydroxyl group, serine is classified as a polar amino acid. ... more
Phenylalanine (abbreviated as Phe or F) is an α-amino acid with the formula C6H5CH2CH(NH2)COOH. This essential amino acid is classified as nonpolar because of the hydrophobic nature of the benzyl side chain. L-Phenylalanine (LPA) is an electrically neutral amino acid used to biochemically form proteins, coded for by DNA. ... more
Testosterone is a steroid hormone from the androgen group and is found in mammals, reptiles, birds, and other vertebrates. In mammals, testosterone is secreted primarily by the testicles of males and the ovaries of females, although small amounts are also secreted by the adrenal glands. ... more
Cysteine (abbreviated as Cys or C) is an α-amino acid with the chemical formula HO2CCH(NH2)CH2SH. It is a semi-essential amino acid, which means that it can be biosynthesized in humans. It is encoded by the codons UGU and UGC. The thiol side chain in cysteine often participates in enzymatic reactions, serving as a nucleophile. ... more
Uracil (U) is one of the four nucleobases in the nucleic acid of RNA that are represented by the letters A, G, C and U. The others are adenine (A), cytosine (C), and guanine (G). In RNA, uracil binds to adenine via two hydrogen bonds. In DNA, the uracil nucleobase is replaced by thymine. ... more
β-Carotene is a strongly colored red-orange pigment abundant in plants and fruits. It is an organic compound and chemically is classified as a hydrocarbon and specifically as a terpenoid (isoprenoid), reflecting its derivation from isoprene units. β-Carotene is biosynthesized from geranylgeranyl pyrophosphate. ... more
Glycerol (also called glycerine or glycerin; see spelling differences) is a simple polyol (sugar alcohol) compound. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. ... more
Thymine (T, Thy) is one of the four nucleobases in the nucleic acid of DNA that are represented by the letters G-C-A-T. The others are adenine, guanine, and cytosine. Thymine is also known as 5-methyluracil, a pyrimidine nucleobase. In RNA, thymine is replaced by the nucleobase uracil. ... more
Tyrosine (abbreviated as Tyr or Y) or 4-hydroxyphenylalanine, is one of the 22 amino acids that are used by cells to synthesize proteins. Its codons are UAC and UAU. It is a non-essential amino acid with a polar side group. The word "tyrosine" is from the Greek tyros, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in the protein casein from cheese. ... more
Sucrose is a sugar, the organic compound commonly known as table sugar, cane sugar, beet sugar or, usually, just sugar. Saccharose is an obsolete name for sugars in general, especially sucrose. A white, odorless, crystalline powder with a sweet taste, it is best known for its role in food. ... more
Lysine (abbreviated as Lys or K) is an α-amino acid with the chemical formula HO2CCH(NH2)(CH2)4NH2. It is an essential amino acid for humans. Lysine's codons are AAA and AAG. Lysine is a base, as are arginine and histidine. The ε-amino group often participates in hydrogen bonding and as a general base in catalysis. ... more
Glutamine (abbreviated as Gln or Q, and often called L-glutamine) is one of the 20 amino acids encoded by the standard genetic code. It is considered a conditionally essential amino acid. Its side-chain is an amide formed by replacing the side-chain hydroxyl of glutamic acid with an amine functional group, making it the amide of glutamic acid. ... more
Dopamine (contracted from 3,4-dihydroxyphenethylamine) is a hormone and neurotransmitter of the catecholamine and phenethylamine families that plays a number of important roles in the human brain and body. Its name derives from its chemical structure: it is an amine that is formed by removing a carboxyl group from a molecule of L-DOPA. ... more
Vanillin is a phenolic aldehyde, which is an organic compound with the molecular formula C8H8O3. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the extract of the vanilla bean. Synthetic vanillin, instead of natural vanilla extract, is now more often used as a flavoring agent in foods, beverages, and pharmaceuticals. ... more
Thiamine or thiamin or vitamin B1, named as the "thio-vitamine" ("sulfur-containing vitamin") is a water-soluble vitamin of the B complex. First named aneurin for the detrimental neurological effects if not present in the diet, it was eventually assigned the generic descriptor name vitamin B1. ... more
Aspartic acid (abbreviated as D-AA, Asp, or D) is an α-amino acid with the chemical formula HOOCCH(NH2)CH2COOH. The carboxylate anion and salts of aspartic acid are known as aspartate. The L-isomer of aspartate is one of the 23 proteinogenic amino acids, i.e., the building blocks of proteins. Its codons are GAU and GAC. ... more
Estradiol, or more precisely, 17β-estradiol, is a human sex hormone and steroid, and the primary female sex hormone. It is named for and is important in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is essential for the development and maintenance of female reproductive tissues but it also has important effects in many other tissues including bone. ... more
Proline (abbreviated as Pro or P) is an α-amino acid, one of the twenty DNA-encoded amino acids. Its codons are CCU, CCC, CCA, and CCG. It is not an essential amino acid, which means that the human body can synthesize it. It is unique among the 20 protein-forming amino acids in that the amine nitrogen is bound to not one but two alkyl groups, thus making it a secondary amine. ... more
phenoxymethylpenicillin (CHEBI:27446)
Phenoxymethylpenicillin, commonly known as penicillin V, is an antibiotic useful for the treatment of a number of bacterial infections. It is a penicillin that is orally active. It is less active than benzylpenicillin (penicillin G) against Gram-negative bacteria. ... more
Folic acid or folate is a B vitamin. It is also referred to as vitamin Ф, vitamin M, vitamin B9, vitamin Bc (or folacin), pteroyl-L-glutamic acid, and pteroyl-L-glutamate . The term folate is often used in the food supplement industry to denote a difference with folic acid; in chemistry the term folate refers to the ion and folic acid to the protonated ion, which both co-exist in water. ... more
5-methylcytosine (CHEBI:27551)
5-Methylcytosine is a methylated form of the DNA base cytosine that may be involved in the regulation of gene transcription. When cytosine is methylated, the DNA maintains the same sequence, but the expression of methylated genes can be altered (the study of this is part of the field of epigenetics). ... more
Histidine (abbreviated as His or H) is an α-amino acid with an imidazole functional group. It is one of the 23 proteinogenic amino acids. Its codons are CAU and CAC. Histidine was first isolated by German physician Albrecht Kossel in 1896. Histidine is an essential amino acid in humans and other mammals. ... more
Caffeine is a bitter, white crystalline xanthine alkaloid found in various seeds, leaves, nuts, and berries. The caffeine ingested by insects when they feed on these plant parts functions as a natural pesticide that can paralyze and kill them. ... more
Tryptophan (IUPAC-IUBMB abbreviation: Trp or W; IUPAC abbreviation: L-Trp or D-Trp; sold for medical use as Tryptan) is one of the 22 standard amino acids and an essential amino acid in the human diet, as demonstrated by its growth effects on rats. It is encoded in the standard genetic code as the codon UGG. ... more
Serotonin or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract (GI tract), platelets, and the central nervous system (CNS) of animals, including humans. ... more
Epinephrine (also known as adrenaline, adrenalin, or β,3,4-trihydroxy-N-methylphenethylamine) is a hormone and a neurotransmitter. Epinephrine and norepinephrine are two separate but related hormones secreted by the medulla of the adrenal glands. They are also produced at the ends of sympathetic nerve fibres, where they serve as chemical mediators for conveying the nerve impulses to effector organs. ... more
Theobromine, formerly known as xantheose, is a bitter alkaloid of the cacao plant, with the chemical formula C7H8N4O2. It is found in chocolate, as well as in a number of other foods, including the leaves of the tea plant, and the kola (or cola) nut. It is classified as a xanthine alkaloid, which also includes the similar compounds theophylline and caffeine. ... more
Arginine (abbreviated as Arg or R) is an α-amino acid. It was first isolated in 1886. The L-form is one of the 20 most common natural amino acids. At the level of molecular genetics, in the structure of the messenger ribonucleic acid mRNA, CGU, CGC, CGA, CGG, AGA, and AGG, are the triplets of nucleotide bases or codons that code for arginine during protein synthesis. ... more
Ascorbic acid is a naturally occurring organic compound with antioxidant properties. It is a white solid, but impure samples can appear yellowish. It dissolves well in water to give mildly acidic solutions. Ascorbic acid is one form ("vitamer") of vitamin C. ... more
Isocitric acid is a protonated form of isocitrate, which is a substrate of the citric acid cycle. Isocitrate is formed from citrate with the help of the enzyme aconitase, and is acted upon by isocitrate dehydrogenase. Salts and esters of isocitric acid are known as isocitrates. ... more
2-oxoglutaric acid (CHEBI:30915)
α-Ketoglutaric acid is one of two ketone derivatives of glutaric acid. The term "ketoglutaric acid," when not further qualified, almost always refers to the alpha variant. β-Ketoglutaric acid varies only by the position of the ketone functional group, and is much less common. ... more
Saccharin is an artificial sweetener with effectively no food energy which is approximately 300 times as sweet as sucrose or table sugar, but has a bitter or metallic aftertaste, especially at high concentrations. It is used to sweeten products such as drinks, candies, cookies, medicines, and toothpaste. ... more
Pyruvic acid (CH3COCOOH) is an organic acid, has a carboxylic acid and a ketone functional group, and is the simplest of the alpha-keto acids. The carboxylate (COO-) anion of pyruvic acid, its Brønsted-Lowry conjugate base, CH3COCOO-, is known as pyruvate, and is a key intersection in several metabolic pathways. ... more
8-hydroxy-2'-deoxyguanosine (CHEBI:40304)
8-Oxo-2'-deoxyguanosine (8-oxo-dG) is an oxidized derivative of deoxyguanosine. 8-oxo-dG is one of the major products of DNA oxidation. Concentrations of 8-oxo-dG within a cell are a measurement of oxidative stress. ... more
Imatinib (INN), marketed by Novartis as Gleevec (Canada, South Africa and the USA) or Glivec (Australia, Europe and Latin America), and sometimes referred to by its investigational name STI-571, is a tyrosine-kinase inhibitor used in the treatment of multiple cancers, most notably Philadelphia chromosome-positive (Ph+) chronic myelogenous leukemia (CML). ... more
Paracetamol, also known as acetaminophen, or APAP, chemically named N-acetyl-p-aminophenol, is a widely used over-the-counter analgesic (pain reliever) and antipyretic (fever reducer). Acetaminophen is the name adopted for this pharmacologic agent in the U. ... more
Vemurafenib (INN, marketed as Zelboraf) is a B-Raf enzyme inhibitor developed by Plexxikon (now part of the Daiichi Sankyo group) and Genentech for the treatment of late-stage melanoma. The name "vemurafenib" comes from V600E mutated BRAF inhibition. Vemurafenib received FDA approval for the treatment of late-stage melanoma on August 17, 2011, making it the first drug designed using fragment-based lead discovery to gain regulatory approval. ... more
(+)-artemisinin (CHEBI:223316)
Artemisinin, also known as Qinghaosu, and its derivatives are a group of drugs that possess the most rapid action of all current drugs against Plasmodium falciparum malaria. Treatments containing an artemisinin derivative (artemisinin-combination therapies, ACTs) are now standard treatment worldwide for P. falciparum malaria. ... more
Glucose (also known as dextrose, or grape sugar) is a simple aldosic monosaccharide found in plants. It is a monosaccharide that is absorbed directly into the bloodstream during digestion. It is an important carbohydrate in biology, which is indicated by the fact that cells use it as a secondary source of energy and a metabolic intermediate. ... more