Page last updated: 2024-10-24
tetrahydrofolate biosynthetic process
Definition
Target type: biologicalprocess
The chemical reactions and pathways resulting in the formation of tetrahydrofolate, 5,6,7,8-tetrahydrofolic acid, a folate derivative bearing additional hydrogens on the pterin group. [ISBN:0198506732]
Tetrahydrofolate (THF) biosynthesis is a critical metabolic pathway that produces tetrahydrofolic acid (THF), a crucial coenzyme involved in various cellular processes, including DNA synthesis, nucleotide metabolism, and amino acid metabolism. THF is derived from dihydrofolate (DHF) through a two-step reduction catalyzed by the enzyme dihydrofolate reductase (DHFR). This process involves the transfer of electrons from NADPH to DHF, resulting in the formation of THF. The biosynthesis of THF can be divided into two major steps: 1. The synthesis of dihydrofolate (DHF): DHF is synthesized from dihydropteroate and p-aminobenzoic acid (PABA) through a series of enzymatic reactions. The first step involves the condensation of dihydropteroate and PABA to form dihydropteroate synthase (DHPS). 2. The reduction of DHF to THF: DHF is then reduced to THF by dihydrofolate reductase (DHFR). DHFR is a highly conserved enzyme found in all living organisms. This process occurs in the cytoplasm of the cell and requires the presence of a reducing agent, such as NADPH. The reduction of DHF to THF is essential for the function of THF in various metabolic pathways. THF acts as a one-carbon carrier in various metabolic reactions. It accepts and transfers one-carbon units at different oxidation states, facilitating the synthesis of purine and pyrimidine bases, amino acids, and other essential biomolecules. The tetrahydrofolate biosynthetic process is tightly regulated, ensuring that sufficient levels of THF are available for cellular function. The availability of THF is critical for cell growth and proliferation. Disruptions in this pathway can lead to various diseases and disorders, including folate deficiency, anemia, neural tube defects, and cancer. The biosynthesis of THF is a vital process that underpins numerous essential metabolic reactions. Understanding this pathway is crucial for developing novel therapeutic strategies for various diseases. '
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Proteins (9)
| Protein | Definition | Taxonomy |
|---|---|---|
| 2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase | A 2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase that is encoded in the genome of Escherichia coli K-12. [PRO:DNx, UniProtKB:P26281] | Escherichia coli K-12 |
| Dihydropteroate synthase | A dihydropteroate synthase that is encoded in the genome of Escherichia coli K-12. [PRO:DNx, UniProtKB:P0AC13] | Escherichia coli K-12 |
| Dihydrofolate reductase | A dihydrofolate reductase folA that is encoded in the genome of Escherichia coli K-12. [PRO:DNx, UniProtKB:P0ABQ4] | Escherichia coli K-12 |
| Dihydrofolate synthase/folylpolyglutamate synthase | A dihydrofolate synthase/folylpolyglutamate synthase that is encoded in the genome of Escherichia coli K-12. [PRO:DNx, UniProtKB:P08192] | Escherichia coli K-12 |
| Dihydrofolate reductase | A protein that is a translation product of the DHFR gene in cow. [PRO:DNx, UniProtKB:P00376] | Bos taurus (cattle) |
| Dihydrofolate reductase | A dihydrofolate reductase that is encoded in the genome of chicken. [PRO:DAN] | Gallus gallus (chicken) |
| Bifunctional purine biosynthesis protein ATIC | A bifunctional purine biosynthesis protein ATIC that is encoded in the genome of human. [PRO:DNx, UniProtKB:P31939] | Homo sapiens (human) |
| Trifunctional purine biosynthetic protein adenosine-3 | A trifunctional purine biosynthetic protein adenosine-3 that is encoded in the genome of human. [PRO:DNx, UniProtKB:P22102] | Homo sapiens (human) |
| Dihydrofolate reductase | A dihydrofolate reductase that is encoded in the genome of human. [PRO:DAN, UniProtKB:P00374] | Homo sapiens (human) |
Compounds (89)
| Compound | Definition | Classes | Roles |
|---|---|---|---|
| hippuric acid | hippuric acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #4591 N-benzoylglycine : An N-acylglycine in which the acyl group is specified as benzoyl. | N-acylglycine | human blood serum metabolite; uremic toxin |
| phenytoin | imidazolidine-2,4-dione | anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent | |
| ag 1295 | quinoxaline derivative | geroprotector | |
| chloroquine | chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis. Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses. | aminoquinoline; organochlorine compound; secondary amino compound; tertiary amino compound | anticoronaviral agent; antimalarial; antirheumatic drug; autophagy inhibitor; dermatologic drug |
| diclofenac | diclofenac : A monocarboxylic acid consisting of phenylacetic acid having a (2,6-dichlorophenyl)amino group at the 2-position. Diclofenac: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt. | amino acid; aromatic amine; dichlorobenzene; monocarboxylic acid; secondary amino compound | antipyretic; drug allergen; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic |
| diflunisal | diflunisal : An organofluorine compound comprising salicylic acid having a 2,4-difluorophenyl group at the 5-position. Diflunisal: A salicylate derivative and anti-inflammatory analgesic with actions and side effects similar to those of ASPIRIN. | monohydroxybenzoic acid; organofluorine compound | non-narcotic analgesic; non-steroidal anti-inflammatory drug |
| etodolac | etodolac : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl moiety. A preferential inhibitor of cyclo-oxygenase 2 and non-steroidal anti-inflammatory, it is used for the treatment of rheumatoid arthritis and osteoarthritis, and for the alleviation of postoperative pain. Administered as the racemate, only the (S)-enantiomer is active. Etodolac: A non-steroidal anti-inflammatory agent and cyclooxygenase-2 (COX-2) inhibitor with potent analgesic and anti-arthritic properties. It has been shown to be effective in the treatment of OSTEOARTHRITIS; RHEUMATOID ARTHRITIS; ANKYLOSING SPONDYLITIS; and in the alleviation of postoperative pain (PAIN, POSTOPERATIVE). | monocarboxylic acid; organic heterotricyclic compound | antipyretic; cyclooxygenase 2 inhibitor; non-narcotic analgesic; non-steroidal anti-inflammatory drug |
| fenbufen | fenbufen: structure; RN given refers to parent cpd | 4-oxo monocarboxylic acid; biphenyls | non-steroidal anti-inflammatory drug |
| ibuprofen | Midol: combination of cinnamedrine, phenacetin, aspirin & caffeine | monocarboxylic acid | antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; geroprotector; non-narcotic analgesic; non-steroidal anti-inflammatory drug; radical scavenger; xenobiotic |
| lamotrigine | 1,2,4-triazines; dichlorobenzene; primary arylamine | anticonvulsant; antidepressant; antimanic drug; calcium channel blocker; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; excitatory amino acid antagonist; geroprotector; non-narcotic analgesic; xenobiotic | |
| mefenamic acid | mefenamic acid : An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis. Mefenamic Acid: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase. | aminobenzoic acid; secondary amino compound | analgesic; antipyretic; antirheumatic drug; EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor; environmental contaminant; non-steroidal anti-inflammatory drug; xenobiotic |
| metformin | metformin : A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1. 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) | guanidines | environmental contaminant; geroprotector; hypoglycemic agent; xenobiotic |
| methazolamide | Methazolamide: A carbonic anhydrase inhibitor that is used as a diuretic and in the treatment of glaucoma. | sulfonamide; thiadiazoles | |
| doxorubicin hydrochloride | folic acids | ||
| pd 153035 | 4-((3-bromophenyl)amino)-6,7-dimethoxyquinazoline: structure given in first source PD-153035 : A member of the class of quinazolines carrying a 3-bromophenylamino substituent at position 4 and two methoxy substituents at positions 6 and 7. | aromatic amine; aromatic ether; bromobenzenes; quinazolines; secondary amino compound | EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; epidermal growth factor receptor antagonist |
| pyrimethamine | Maloprim: contains above 2 cpds | aminopyrimidine; monochlorobenzenes | antimalarial; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor |
| riluzole | Riluzole: A glutamate antagonist (RECEPTORS, GLUTAMATE) used as an anticonvulsant (ANTICONVULSANTS) and to prolong the survival of patients with AMYOTROPHIC LATERAL SCLEROSIS. | benzothiazoles | |
| imatinib | aromatic amine; benzamides; N-methylpiperazine; pyridines; pyrimidines | antineoplastic agent; apoptosis inducer; tyrosine kinase inhibitor | |
| sulfacetamide | sulfacetamide : A sulfonamide that is sulfanilamide acylated on the sulfonamide nitrogen. Sulfacetamide: An anti-bacterial agent that is used topically to treat skin infections and orally for urinary tract infections. | N-sulfonylcarboxamide; substituted aniline | antibacterial drug; antiinfective agent; antimicrobial agent; EC 2.5.1.15 (dihydropteroate synthase) inhibitor |
| sulfamethoxazole | sulfamethoxazole : An isoxazole (1,2-oxazole) compound having a methyl substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 3-position. Sulfamethoxazole: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208) | isoxazoles; substituted aniline; sulfonamide; sulfonamide antibiotic | antibacterial agent; antiinfective agent; antimicrobial agent; drug allergen; EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; epitope; P450 inhibitor; xenobiotic |
| sulfasalazine | sulfasalazine : An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position. Sulfasalazine: A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see MESALAMINE) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907) | ||
| sulfathiazole | sulfathiazole : A 1,3-thiazole compound having a 4-aminobenzenesulfonamido group at the 2-position. Sulfathiazole: A sulfathiazole compound that is used as a short-acting anti-infective agent. It is no longer commonly used systemically due to its toxicity, but may still be applied topically in combination with other drugs for the treatment of vaginal and skin infections, and is still used in veterinary medicine. | 1,3-thiazoles; substituted aniline; sulfonamide; sulfonamide antibiotic | antiinfective agent; drug allergen; EC 2.5.1.15 (dihydropteroate synthase) inhibitor; environmental contaminant; xenobiotic |
| trimethoprim | trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge. Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported. | aminopyrimidine; methoxybenzenes | antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic |
| trimetrexate | Trimetrexate: A nonclassical folic acid inhibitor through its inhibition of the enzyme dihydrofolate reductase. It is being tested for efficacy as an antineoplastic agent and as an antiparasitic agent against PNEUMOCYSTIS PNEUMONIA in AIDS patients. Myelosuppression is its dose-limiting toxic effect. | ||
| veratridine | steroid | sodium channel modulator | |
| tryptophan | tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3. 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. | erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; L-alpha-amino acid zwitterion; proteinogenic amino acid; tryptophan; tryptophan zwitterion | antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite |
| phenformin | phenformin : A member of the class of biguanides that is biguanide in which one of the terminal nitrogen atoms is substituted by a 2-phenylethyl group. It was used as an anti-diabetic drug but was later withdrawn from the market due to potential risk of lactic acidosis. Phenformin: A biguanide hypoglycemic agent with actions and uses similar to those of METFORMIN. Although it is generally considered to be associated with an unacceptably high incidence of lactic acidosis, often fatal, it is still available in some countries. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290) | biguanides | antineoplastic agent; geroprotector; hypoglycemic agent |
| cycloguanil | cycloguanil : A triazine in which a 1,6-dihydro-1,3,5-triazine ring is substituted at N-1 by a 4-chlorophenyl group, at C-2 and -4 by amino groups and at C-6 by gem-dimethyl groups. A dihydrofolate reductase inhibitor, it is a metabolite of the antimalarial drug proguanil. cycloguanil: the active metabolite of proguanil; antifolate drug; structure in first source | triazines | antifolate; antiinfective agent; antimalarial; antiparasitic agent; antiprotozoal drug; EC 1.5.1.3 (dihydrofolate reductase) inhibitor |
| D-tryptophan | D-alpha-amino acid; tryptophan; tryptophan zwitterion | bacterial metabolite | |
| congo red | Congo Red : An indicator dye that is blue-violet at pH 3.0 and red at pH 5.0. Congo Red: An acid dye used in testing for hydrochloric acid in gastric contents. It is also used histologically to test for AMYLOIDOSIS. | bis(azo) compound | |
| 4,6-diamino-2,2-dimethyl-1,2-dihydro-1-phenyl-s-triazine | 4,6-diamino-2,2-dimethyl-1,2-dihydro-1-phenyl-s-triazine: structure in first source | ||
| diaveridine | diaveridine : An aminopyrimidine in which the pyrimidine ring carries amino substituents at C-2 and C-4 and a 3,4-dimethoxybenzyl group at C-5. A folic acid antagonist, it is used as a synergist with sulfonamides against the parasitic Eimeria species. diaveridine: RN given refers to parent cpd; structure | aminopyrimidine | antiparasitic agent; drug allergen |
| piritrexim | piritrexim: RN given refers to parent cpd; structure given in first source | ||
| brequinar | brequinar : A quinolinemonocarboxylic acid that is quinoline substituted by 2'-fluoro[1,1'-biphenyl]-4-yl, methyl, carboxy and fluoro groups at positions 2, 3, 4, and 6, respectively. It is an inhibitor of dihydroorotate dehydrogenase, an enzyme that is required for de novo pyrimidine biosynthesis. The compound exhibits antineoplastic and antiviral properties. | biphenyls; monocarboxylic acid; monofluorobenzenes; quinolinemonocarboxylic acid | anticoronaviral agent; antimetabolite; antineoplastic agent; antiviral agent; EC 1.3.5.2 [dihydroorotate dehydrogenase (quinone)] inhibitor; immunosuppressive agent; pyrimidine synthesis inhibitor |
| epigallocatechin gallate | (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin. epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis) | flavans; gallate ester; polyphenol | antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite |
| 2,4-diaminoquinazoline | |||
| aica ribonucleotide | AICA ribonucleotide : A 1-(phosphoribosyl)imidazolecarboxamide that is acadesine in which the hydroxy group at the 5' position has been converted to its monophosphate derivative. AICA ribonucleotide: purine precursor that has antineoplastic activity | 1-(phosphoribosyl)imidazolecarboxamide; aminoimidazole | cardiovascular drug; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite |
| tetroxoprim | tetroxoprim: structure given in Negwer 5th ed, #6419 | dimethoxybenzene | |
| isocytosine | 2-amino-4-hydroxypyrimidine : An aminopyrimidine in which the pyrimidine ring bears amino and hydroxy substituents at positions 2 and 4, respectively. | aminopyrimidine; pyrimidine nucleobase; pyrimidone | |
| 2,4-diaminopyrimidine | 2,6-diaminopyrimidine: structure in first source pyrimidine-2,4-diamine : An aminopyrimidine in which a pyrimidine nucleus is substituted with amino groups at C-2 and C-4. | aminopyrimidine | |
| metioprim | |||
| aditoprim | aditoprim: structure given in first source | ||
| brodimoprim | brodimoprim : An aminopyrimidine that is 2,4-diaminopyrimidine in which the hydrogen at position 5 has been replaced by a 4-bromo-3,5-dimethoxybenzyl group. brodimoprim: inhibits dihydrofolate reductase | aminopyrimidine; bromobenzenes; methoxybenzenes | antibacterial drug; antiinfective agent; EC 1.5.1.3 (dihydrofolate reductase) inhibitor |
| epiroprim | epiroprim: an analog of trimethoprim with improved antimicrobial and pharmacokinetic properties; structure given in first source | ||
| methylbenzoprim | methylbenzoprim: structure given in first source | ||
| sori 8895 | SoRI 8895: RN in first source | ||
| sori 8890 | SoRI 8890: RN in first source | ||
| iodophthalein | |||
| isoguanine | isoguanine : An oxopurine that is 3,7-dihydro-purin-2-one in which the hydrogen at position 6 is substituted by an amino group. isoguanine: structure | oxopurine | |
| 2,4-diamino-5-benzylpyrimidine | 2,4-diamino-5-benzylpyrimidine: structure given in first source | ||
| 2,4-diamino-5,6-dihydro-6,6-dimethyl-5-(4'-methoxyphenyl)-s-triazine | 2,4-diamino-5,6-dihydro-6,6-dimethyl-5-(4'-methoxyphenyl)-s-triazine: RN given refers to parent cpd; structure given in first source | ||
| 10-deazaaminopterin | |||
| epicatechin gallate | (-)-epicatechin-3-O-gallate : A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida. epicatechin gallate: a steroid 5alpha-reductase inhibitor; RN given refers to the (cis)-isomer; structure given in first source; isolated from green tea | catechin; gallate ester; polyphenol | EC 3.2.1.1 (alpha-amylase) inhibitor; EC 3.2.1.20 (alpha-glucosidase) inhibitor; metabolite |
| wr 99210 | BRL 6231: RN given refers to parent cpd; NM & N1 refer to HCl; synonym BRL 51084 refers to (mono-HBr); structure | ||
| methotrexate | dicarboxylic acid; monocarboxylic acid amide; pteridines | abortifacient; antimetabolite; antineoplastic agent; antirheumatic drug; dermatologic drug; DNA synthesis inhibitor; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; immunosuppressive agent | |
| 10-propargyl-10-deazaaminopterin | 10-propargyl-10-deazaaminopterin: structure in first source pralatrexate : A pteridine that is the N-4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]benzoyl derivative of L-glutamic acid. Used for treatment of Peripheral T-Cell Lymphoma, an aggressive form of non-Hodgkins lymphoma. | N-acyl-L-glutamic acid; pteridines; terminal acetylenic compound | antimetabolite; antineoplastic agent; EC 1.5.1.3 (dihydrofolate reductase) inhibitor |
| naproxen | naproxen : A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes. Naproxen: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout. | methoxynaphthalene; monocarboxylic acid | antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; drug allergen; environmental contaminant; gout suppressant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic |
| n-(4-(n-((2,4-diaminofuro(2,3-d)pyrimidin-5-yl)methyl)amino)benzoyl)glutamic acid | N-(4-(N-((2,4-diaminofuro(2,3-d)pyrimidin-5-yl)methyl)amino)benzoyl)glutamic acid: structure given in first source | ||
| 5-formamidoimidazole-4-carboxamide ribotide | 5-formamidoimidazole-4-carboxamide ribotide: purine precursor | 1-(phosphoribosyl)imidazolecarboxamide | Escherichia coli metabolite; mouse metabolite |
| aminopterin | Aminopterin: A folic acid derivative used as a rodenticide that has been shown to be teratogenic. | dicarboxylic acid | EC 1.5.1.3 (dihydrofolate reductase) inhibitor; mutagen |
| 4-aminobenzoylglutamic acid | 4-aminobenzoylglutamic acid: RN given refers to (L)-isomer N-(4-aminobenzoyl)-L-glutamic acid : A dipeptide resulting from the formal condensation of the carboxylic acid group of 4-aminobenzoic acid with the amino group of L-glutamic acid. | dicarboxylic acid; dipeptide; N-acyl-L-alpha-amino acid; substituted aniline | |
| iclaprim | 5-[(2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)methyl]pyrimidine-2,4-diamine : An aminopyrimidine that is 5-methylpyrimidine-2,4-diamine in which one of the hydrogens of the methyl group has been replaced by a 2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl group. iclaprim : A racemate consisting of equimolar amounts of (R)- and (S)-iclaprim. Both enantiomers exhibit similar, potent bactericidal activity against major Gram-positive pathogens, notably methicillin-sensitive and -resistant Staphylococcus aureus (MSSA and MRSA, respectively). iclaprim: has antiviral activity | aminopyrimidine; chromenes; cyclopropanes | |
| n-(3-chloro-7-indolyl)-1,4-benzenedisulphonamide | indisulam : A chloroindole that is 3-chloro-1H-indole substituted by a [(4-sulfamoylphenyl)sulfonyl]nitrilo group at position 7. It is a carbonic anhydrase inhibitor and a potential anti-cancer agent currently in clinical development. N-(3-chloro-7-indolyl)-1,4-benzenedisulphonamide: structure in first source | chloroindole; organochlorine compound; sulfonamide | antineoplastic agent; EC 4.2.1.1 (carbonic anhydrase) inhibitor |
| nsc 88915 | 4-pregnen-21-ol-3,20-dione-21-(4-bromobenzenesufonate): a tyrosyl-DNA phosphodiesterase inhibitor; structure in first source | ||
| pd 173955 | PD 173955: inhibits src family-selective tyrosine kinase; structure in first source | aryl sulfide; dichlorobenzene; methyl sulfide; pyridopyrimidine | tyrosine kinase inhibitor |
| chalcone | trans-chalcone : The trans-isomer of chalcone. | chalcone | EC 3.2.1.1 (alpha-amylase) inhibitor |
| flavin mononucleotide | flavin mononucleotide; vitamin B2 | bacterial metabolite; coenzyme; cofactor; human metabolite; mouse metabolite | |
| 4,4-dimethyl-N2-(2-methylphenyl)-1H-1,3,5-triazine-2,6-diamine | substituted aniline | ||
| 1-methyltryptophan | 1-methyltryptophan : A tryptophan derivative that is tryptophan carrying a single methyl substituent at position 1 on the indole. 1-methyltryptophan: an immunomodulator | indolyl carboxylic acid | |
| thioguanine anhydrous | Thioguanine: An antineoplastic compound which also has antimetabolite action. The drug is used in the therapy of acute leukemia. tioguanine : A 2-aminopurine that is the 6-thiono derivative of 2-amino-1,9-dihydro-6H-purine. Incorporates into DNA and inhibits synthesis. Used in the treatment of leukaemia. | 2-aminopurines | anticoronaviral agent; antimetabolite; antineoplastic agent |
| semaxinib | semaxanib : 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 |
| edatrexate | edatrexate: structure given in first source | glutamic acid derivative | |
| gentamicin sulfate | |||
| teriflunomide | (trifluoromethyl)benzenes; aromatic amide; enamide; enol; nitrile; secondary carboxamide | drug metabolite; EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor; hepatotoxic agent; non-steroidal anti-inflammatory drug; tyrosine kinase inhibitor | |
| dihydrofolate | dihydrofolic acid : A folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid. It interacts with bacteria during cell division and is targeted by various drugs to prevent nucleic acid synthesis. | dihydrofolic acids | Escherichia coli metabolite; mouse metabolite |
| guanine | 2-aminopurines; oxopurine; purine nucleobase | algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite | |
| folic acid | folcysteine: used to promote fertility in chickens vitamin B9 : Any B-vitamin that exhibits biological activity against vitamin B9 deficiency. Vitamin B9 refers to the many forms of folic acid and its derivatives, including tetrahydrofolic acid (the active form), methyltetrahydrofolate (the primary form found in blood), methenyltetrahydrofolate, folinic acid amongst others. They are present in abundance in green leafy vegetables, citrus fruits, and animal products. Lack of vitamin B9 leads to anemia, a condition in which the body cannot produce sufficient number of red blood cells. Symptoms of vitamin B9 deficiency include fatigue, muscle weakness, and pale skin. | folic acids; N-acyl-amino acid | human metabolite; mouse metabolite; nutrient |
| raltitrexed | N-acyl-amino acid | ||
| n-(4(n-((2-amino-4-hydroxy-6-quinazolinyl)methyl)prop-2-ynylamino)benzoyl)-l-glutamic acid | |||
| leucovorin | 5-formyltetrahydrofolic acid : A formyltetrahydrofolic acid in which the formyl group is located at position 5. | formyltetrahydrofolic acid | Escherichia coli metabolite; mouse metabolite |
| 1843u89 | 1843U89: structure given in first source; a folate analog | ||
| 5,11-methenyltetrahydrohomofolate | |||
| pemetrexed | pemetrexed disodium : An organic sodium salt that is the disodium salt of N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid. Inhibits thymidylate synthase (TS), 421 dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT). | N-acyl-L-glutamic acid; pyrrolopyrimidine | antimetabolite; antineoplastic agent; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; EC 2.1.1.45 (thymidylate synthase) inhibitor; EC 2.1.2.2 (phosphoribosylglycinamide formyltransferase) inhibitor |
| lometrexol | lometrexol: RN & structure given in first source; | ||
| 8-methylguanine | 8-methylguanine: structure given in first source | ||
| 2-amino-6-hydroxy-8-mercaptopurine | |||
| cb 3717 | N-acyl-L-glutamic acid | ||
| (5)n,(8)n-deaza-(10)-n-methylfolate | |||
| 5,6,7,8-tetrahydrofolic acid | tetrahydrofolate : A folate obtained by deprotonation of any tetrahydrofolic acid. tetrahydrofolic acid : A group of heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with one or more L-glutamic acid units. | tetrahydrofolic acid | Saccharomyces cerevisiae metabolite |