CHEBI:8502 - 6-propyl-2-thiouracil

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ChEBI Name 6-propyl-2-thiouracil
ChEBI ID CHEBI:8502
Definition A pyrimidinethione consisting of uracil in which the 2-oxo group is substituted by a thio group and the hydrogen at position 6 is substituted by a propyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000013508431
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Testosterone is the primary male sex hormone and androgen in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testicles and prostate, as well as promoting secondary sexual characteristics such as increased muscle and bone mass, and the growth of body hair. It is associated with increased aggression, sex drive, dominance, courtship display, and a wide range of behavioral characteristics. In addition, testosterone in both sexes is involved in health and well-being, where it has a significant effect on overall mood, cognition, social and sexual behavior, metabolism and energy output, the cardiovascular system, and in the prevention of osteoporosis. Insufficient levels of testosterone in men may lead to abnormalities including frailty, accumulation of adipose fat tissue within the body, anxiety and depression, sexual performance issues, and bone loss. Excessive levels of testosterone in men may be associated with hyperandrogenism, higher risk of heart failure, increased mortality in men with prostate cancer, and male pattern baldness. Testosterone is a steroid hormone from the androstane class containing a ketone and a hydroxyl group at positions three and seventeen respectively. It is biosynthesized in several steps from cholesterol and is converted in the liver to inactive metabolites. It exerts its action through binding to and activation of the androgen receptor. In humans and most other vertebrates, testosterone is secreted primarily by the testicles of males and, to a lesser extent, the ovaries of females. On average, in adult males, levels of testosterone are about seven to eight times as great as in adult females. As the metabolism of testosterone in males is more pronounced, the daily production is about 20 times greater in men. Females are also more sensitive to the hormone. In addition to its role as a natural hormone, testosterone is used as a medication to treat hypogonadism and breast cancer. Since testosterone levels decrease as men age, testosterone is sometimes used in older men to counteract this deficiency. It is also used illicitly to enhance physique and performance, for instance in athletes. The World Anti-Doping Agency lists it as S1 Anabolic agent substance "prohibited at all times".
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Formula C7H10N2OS
Net Charge 0
Average Mass 170.23200
Monoisotopic Mass 170.05138
InChI InChI=1S/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11)
InChIKey KNAHARQHSZJURB-UHFFFAOYSA-N
SMILES CCCc1cc(=O)[nH]c(=S)[nH]1
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): antithyroid drug
A drug used to treat hyperthyroidism by reducing the excessive production of thyroid hormones.
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
antimetabolite
A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
hormone antagonist
A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.
EC 1.14.13.39 (nitric oxide synthase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of nitric oxide synthase (EC 1.14.13.39).
Application(s): antithyroid drug
A drug used to treat hyperthyroidism by reducing the excessive production of thyroid hormones.
hormone antagonist
A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.
antidote to paracetamol poisoning
A role borne by a molecule that acts to counteract or neutralize the deleterious effects of paracetamol (acetaminophen).
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ChEBI Ontology
Outgoing 6-propyl-2-thiouracil (CHEBI:8502) has functional parent uracil (CHEBI:17568)
6-propyl-2-thiouracil (CHEBI:8502) has role antidote to paracetamol poisoning (CHEBI:74529)
6-propyl-2-thiouracil (CHEBI:8502) has role antimetabolite (CHEBI:35221)
6-propyl-2-thiouracil (CHEBI:8502) has role antioxidant (CHEBI:22586)
6-propyl-2-thiouracil (CHEBI:8502) has role antithyroid drug (CHEBI:50671)
6-propyl-2-thiouracil (CHEBI:8502) has role carcinogenic agent (CHEBI:50903)
6-propyl-2-thiouracil (CHEBI:8502) has role EC 1.14.13.39 (nitric oxide synthase) inhibitor (CHEBI:61908)
6-propyl-2-thiouracil (CHEBI:8502) has role hormone antagonist (CHEBI:49020)
6-propyl-2-thiouracil (CHEBI:8502) is a pyrimidinethione (CHEBI:48546)
Incoming 6-(2-hydroxyethyl)-2-sulfanylidene-1H-pyrimidin-4-one (CHEBI:140206) has functional parent 6-propyl-2-thiouracil (CHEBI:8502)
IUPAC Name
6-propyl-2-sulfanylidene-2,3-dihydropyrimidin-4(1H)-one
INNs Sources
propiltiouracilo ChemIDplus
propylthiouracil ChemIDplus
propylthiouracile ChemIDplus
propylthiouracilum ChemIDplus
Synonyms Sources
2,3-dihydro-6-propyl-2-thioxo-4(1H)-pyrimidinone NIST Chemistry WebBook
2-Mercapto-6-propyl-4-pyrimidone ChemIDplus
2-Mercapto-6-propylpyrimid-4-one NIST Chemistry WebBook
2-Thio-4-oxo-6-propyl-1,3-pyrimidine ChemIDplus
2-Thio-6-propyl-1,3-pyrimidin-4-one ChemIDplus
4-Propyl-2-thiouracil ChemIDplus
4-propyl-2-thiouracil ChemIDplus
6-Propyl-2-thio-2,4(1H,3H)pyrimidinedione ChemIDplus
6-propyl-2-thiouracil ChemIDplus
6-propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one IUPAC
6-Propylthiouracil ChemIDplus
6-Thio-4-propyluracil NIST Chemistry WebBook
Propylthiouracil KEGG COMPOUND
Manual Xrefs Databases
2308 DrugCentral
C07569 KEGG COMPOUND
D00562 KEGG DRUG
DB00550 DrugBank
HMDB0014690 HMDB
LSM-5592 LINCS
Propylthiouracil Wikipedia
View more database links
Registry Numbers Types Sources
130039 Reaxys Registry Number Reaxys
1998546 Gmelin Registry Number Gmelin
51-52-5 CAS Registry Number NIST Chemistry WebBook
51-52-5 CAS Registry Number ChemIDplus
Citations Types Sources
11005705 PubMed citation Europe PMC
11036881 PubMed citation Europe PMC
11350963 PubMed citation Europe PMC
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16380675 PubMed citation Europe PMC
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19578601 PubMed citation Europe PMC
20166204 PubMed citation Europe PMC
21749382 PubMed citation Europe PMC
6387489 PubMed citation Europe PMC
Last Modified
26 August 2022
General Comment
2014-07-14 Propylthiouracil can be found in blood and urine samples of individuals who have taken this drug.