CHEBI:90926 - tenofovir alafenamide

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ChEBI Name tenofovir alafenamide
ChEBI ID CHEBI:90926
Definition An L-alanine derivative that is isopropyl L-alaninate in which one of the amino hydrogens is replaced by an (S)-({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(phenoxy)phosphoryl group. A prodrug for tenofovir, it is used (as the fumarate salt) in combination therapy for the treatment of HIV-1 infection.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H29N6O5P
Net Charge 0
Average Mass 476.467
Monoisotopic Mass 476.194
InChI InChI=1S/C21H29N6O5P/c1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24)/t15-,16+,33+/m1/s1
InChIKey LDEKQSIMHVQZJK-CAQYMETFSA-N
SMILES N1=CN=C2C(=C1N)N=CN2C[C@H](OC[P@](N[C@H](C(OC(C)C)=O)C)(=O)OC3=CC=CC=C3)C
Roles Classification
Biological Role(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
Application(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing tenofovir alafenamide (CHEBI:90926) has functional parent adenine (CHEBI:16708)
tenofovir alafenamide (CHEBI:90926) has role antiviral drug (CHEBI:36044)
tenofovir alafenamide (CHEBI:90926) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
tenofovir alafenamide (CHEBI:90926) has role prodrug (CHEBI:50266)
tenofovir alafenamide (CHEBI:90926) is a 6-aminopurines (CHEBI:20706)
tenofovir alafenamide (CHEBI:90926) is a L-alanine derivative (CHEBI:83943)
tenofovir alafenamide (CHEBI:90926) is a ether (CHEBI:25698)
tenofovir alafenamide (CHEBI:90926) is a isopropyl ester (CHEBI:35725)
tenofovir alafenamide (CHEBI:90926) is a phosphoramidate ester (CHEBI:27577)
tenofovir alafenamide (CHEBI:90926) is conjugate base of tenofovir alafenamide(1+) (CHEBI:90927)
Incoming tenofovir alafenamide(1+) (CHEBI:90927) is conjugate acid of tenofovir alafenamide (CHEBI:90926)
IUPAC Name
propan-2-yl N-[(S)-({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(phenoxy)phosphoryl]-L-alaninate
INN Source
tenofovir alafenamide KEGG DRUG
Synonyms Sources
GS 7340 ChemIDplus
GS-7340 ChemIDplus
TAF ChemIDplus
Manual Xrefs Databases
4944 DrugCentral
D10428 KEGG DRUG
DB09299 DrugBank
Tenofovir_alafenamide Wikipedia
View more database links
Registry Numbers Types Sources
379270-37-8 CAS Registry Number ChemIDplus
379270-37-8 CAS Registry Number KEGG DRUG
8948831 Reaxys Registry Number Reaxys
Last Modified
09 March 2018