tenofovir alafenamide

CHEBI:90926 ·resolve ·ANTIVIRAL ·EXACT SEEDED

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. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:20706 CHEBI:20706
CHEBI:25698 CHEBI:25698
CHEBI:27577 CHEBI:27577
CHEBI:35725 CHEBI:35725
CHEBI:83943 CHEBI:83943

Chemical structure

Computed structure properties
Molecular formula	C21H29N6O5P
Charge	0
Average mass	476.474 Da
Monoisotopic mass	476.1937 Da
Source	ChEBI
InChIKey	LDEKQSIMHVQZJK-CAQYMETFSA-N

SMILES

CC(C)OC(=O)[C@H](C)N[P@](=O)(CO[C@H](C)Cn1cnc2c(N)ncnc21)Oc1ccccc1

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

Also called

propan-2-yl N-[(S)-({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(phenoxy)phosphoryl]-L-alaninate (EXACT_SYNONYM)— chebi
GS 7340 (EXACT_SYNONYM)— chebi
GS-7340 (EXACT_SYNONYM)— chebi
TAF (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:379270-37-8
drugbank:DB09299
drugcentral:4944
kegg.drug:D10428
reaxys:8948831
wikipedia.en:Tenofovir_alafenamide

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:36044 CHEBI:36044
CHEBI:53756 CHEBI:53756

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:90926`	tenofovir alafenamide	`antibioticmech:chebi-1c3df758b9`	2026-08-30

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION microbial target — Assigned from ChEBI role CHEBI:53756 (HIV-1 reverse transcriptase inhibitor). ChEBI asserts the role on the compound. The role names a target specific to the microbe or virus — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.