CHEBI:83766 - olaparib

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ChEBI Name olaparib
ChEBI ID CHEBI:83766
Definition A member of the class of N-acylpiperazines obtained by formal condensation of the carboxy group of 2-fluoro-5-[(4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid with the free amino group of N-(cyclpropylcarbonyl)piperazine; used to treat advanced ovarian cancer.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kimberly Van Auken
Supplier Information No supplier information found for this compound.
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Acetyl-CoA (acetyl coenzyme A) is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Its main function is to deliver the acetyl group to the citric acid cycle (Krebs cycle) to be oxidized for energy production. Coenzyme A (CoASH or CoA) consists of a β-mercaptoethylamine group linked to pantothenic acid (vitamin B5) through an amide linkage and 3'-phosphorylated ADP. The acetyl group (indicated in blue in the structural diagram on the right) of acetyl-CoA is linked to the sulfhydryl substituent of the β-mercaptoethylamine group. This thioester linkage is a "high energy" bond, which is particularly reactive. Hydrolysis of the thioester bond is exergonic (−31.5 kJ/mol). CoA is acetylated to acetyl-CoA by the breakdown of carbohydrates through glycolysis and by the breakdown of fatty acids through β-oxidation. Acetyl-CoA then enters the citric acid cycle, where the acetyl group is oxidized to carbon dioxide and water, and the energy released is captured in the form of 11 ATP and one GTP per acetyl group. Konrad Bloch and Feodor Lynen were awarded the 1964 Nobel Prize in Physiology or Medicine for their discoveries linking acetyl-CoA and fatty acid metabolism. Fritz Lipmann won the Nobel Prize in 1953 for his discovery of the cofactor coenzyme A.
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Formula C24H23FN4O3
Net Charge 0
Average Mass 434.46280
Monoisotopic Mass 434.17542
InChI InChI=1S/C24H23FN4O3/c25-20-8-5-15(14-21-17-3-1-2-4-18(17)22(30)27-26-21)13-19(20)24(32)29-11-9-28(10-12-29)23(31)16-6-7-16/h1-5,8,13,16H,6-7,9-12,14H2,(H,27,30)
InChIKey FDLYAMZZIXQODN-UHFFFAOYSA-N
SMILES Fc1ccc(Cc2n[nH]c(=O)c3ccccc23)cc1C(=O)N1CCN(CC1)C(=O)C1CC1
Roles Classification
Biological Role(s): EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor
An EC 2.4.2.* (pentosyltransferase) inhibitor that interferes with the action of a NAD+ ADP-ribosyltransferase (EC 2.4.2.30).
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing olaparib (CHEBI:83766) has role antineoplastic agent (CHEBI:35610)
olaparib (CHEBI:83766) has role apoptosis inducer (CHEBI:68495)
olaparib (CHEBI:83766) has role EC 2.4.2.30 (NAD+ ADP-ribosyltransferase) inhibitor (CHEBI:62913)
olaparib (CHEBI:83766) is a N-acylpiperazine (CHEBI:46844)
olaparib (CHEBI:83766) is a cyclopropanes (CHEBI:51454)
olaparib (CHEBI:83766) is a monofluorobenzenes (CHEBI:83575)
olaparib (CHEBI:83766) is a phthalazines (CHEBI:38768)
IUPAC Name
4-(3-{[4-(cyclopropylcarbonyl)piperazin-1-yl]carbonyl}-4-fluorobenzyl)phthalazin-1(2H)-one
INN Source
olaparib KEGG DRUG
Synonyms Sources
AZD-2281 SUBMITTER
AZD2281 SUBMITTER
KU59436 SUBMITTER
Brand Name Source
Lynparza SUBMITTER
Manual Xrefs Databases
09L PDBeChem
4907 DrugCentral
D09730 KEGG DRUG
LSM-1145 LINCS
Olaparib Wikipedia
View more database links
Registry Numbers Types Sources
12051534 Reaxys Registry Number Reaxys
763113-22-0 CAS Registry Number ChemIDplus
763113-22-0 CAS Registry Number KEGG DRUG
Citations
Last Modified
22 February 2017