CHEBI:76010 - dolutegravir

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ChEBI Name dolutegravir
ChEBI ID CHEBI:76010
Definition A monocarboxylic acid amide obtained by formal condensation of the carboxy group of (4R,12aS)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxylic acid with the amino group of 2,4-difluorobenzylamine. Used (as its sodium salt) for treatment of HIV-1.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H19F2N3O5
Net Charge 0
Average Mass 419.37880
Monoisotopic Mass 419.129
InChI InChI=1S/C20H19F2N3O5/c1-10-4-5-30-15-9-24-8-13(17(26)18(27)16(24)20(29)25(10)15)19(28)23-7-11-2-3-12(21)6-14(11)22/h2-3,6,8,10,15,27H,4-5,7,9H2,1H3,(H,23,28)/t10-,15+/m1/s1
InChIKey RHWKPHLQXYSBKR-BMIGLBTASA-N
SMILES C[C@@H]1CCO[C@H]2Cn3cc(C(=O)NCc4ccc(F)cc4F)c(=O)c(O)c3C(=O)N12
Roles Classification
Biological Role(s): HIV-1 integrase inhibitor
An inhibitor of HIV-1 integrase, an enzyme required for the integration of the genetic material of the retrovirus into the DNA of the infected cells.
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ChEBI Ontology
Outgoing dolutegravir (CHEBI:76010) has role HIV-1 integrase inhibitor (CHEBI:67268)
dolutegravir (CHEBI:76010) is a monocarboxylic acid amide (CHEBI:29347)
dolutegravir (CHEBI:76010) is a organic heterotricyclic compound (CHEBI:26979)
dolutegravir (CHEBI:76010) is a organofluorine compound (CHEBI:37143)
dolutegravir (CHEBI:76010) is conjugate acid of dolutegravir(1−) (CHEBI:76014)
Incoming dolutegravir(1−) (CHEBI:76014) is conjugate base of dolutegravir (CHEBI:76010)
IUPAC Name
(4R,12aS)-N-(2,4-difluorobenzyl)-7-hydroxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide
Synonym Source
S/GSK1349572 ChemIDplus
Manual Xrefs Databases
4805 DrugCentral
D10066 KEGG DRUG
DLU PDBeChem
Dolutegravir Wikipedia
EP2602260 Patent
WO2006116764 Patent
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Registry Numbers Types Sources
1051375-16-6 CAS Registry Number KEGG DRUG
1051375-16-6 CAS Registry Number ChemIDplus
12732602 Reaxys Registry Number Reaxys
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Last Modified
22 February 2017