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CHEBI:90926 - tenofovir alafenamide

ChEBI IDCHEBI:90926
ChEBI Nametenofovir alafenamide
Stars
DefinitionAn 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.
Last Modified9 March 2018
SubmitterSteve
DownloadsMolfile
FormulaC21H29N6O5P
Net Charge0
Average Mass476.474
Monoisotopic Mass476.19370
SMILESCC(C)OC(=O)[C@H](C)N[P@](=O)(CO[C@H](C)Cn1cnc2c(N)ncnc21)Oc1ccccc1
InChIInChI=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
InChIKeyLDEKQSIMHVQZJK-CAQYMETFSA-N
Wikipedia
Roles Classification
Biological Roles:
HIV-1 reverse transcriptase inhibitor  An entity which inhibits the activity of HIV-1 reverse transcriptase.
antiviral drug  A substance used in the prophylaxis or therapy of virus diseases.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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 L-alanine derivative (CHEBI:83943)
tenofovir alafenamide (CHEBI:90926) is a 6-aminopurines (CHEBI:20706)
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 Relation(s)
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 alafenamideKEGG DRUG
Synonyms  Source
GS-7340ChemIDplus
TAFChemIDplus
GS 7340ChemIDplus
Manual XrefsDatabases
D10428KEGG DRUG
Tenofovir_alafenamideWikipedia
DB09299DrugBank
4944DrugCentral
Registry NumbersSources
Reaxys:8948831Reaxys
CAS:379270-37-8KEGG DRUG
CAS:379270-37-8ChemIDplus