entecavir (anhydrous)

CHEBI:473990 ·resolve ·ANTIVIRAL ·EXACT SEEDED

Guanine substituted at the 9 position by a 4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl group. A synthetic analogue of 2'-deoxyguanosine, it is a nucleoside reverse transcriptase inhibitor with selective antiviral activity against hepatitis B virus. Entecavir is phosphorylated intracellularly to the active triphosphate form, which competes with deoxyguanosine triphosphate, the natural substrate of hepatitis B virus reverse transcriptase, inhibiting every stage of the enzyme's activity, although it has no activity against HIV. It is used for the treatment of chronic hepatitis B. — 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:15734 CHEBI:15734
CHEBI:20702 CHEBI:20702
CHEBI:25810 CHEBI:25810
CHEBI:35681 CHEBI:35681

Chemical structure

Computed structure properties
Molecular formula	C12H15N5O3
Charge	0
Average mass	277.284 Da
Monoisotopic mass	277.11749 Da
Source	ChEBI
InChIKey	QDGZDCVAUDNJFG-FXQIFTODSA-N

SMILES

C=C1[C@H](CO)[C@@H](O)C[C@@H]1n1cnc2c(=O)nc(N)nc21

InChI

InChI=1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8-/m0/s1

Also called

entecavir (INN)— chebi
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

beilstein:7692760
cas:142217-69-4
drugbank:DB00442
drugcentral:1019
kegg.drug:D07896
lincs.smallmolecule:LSM-5258

Activity roles

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

CHEBI:36044 CHEBI:36044
CHEBI:59897 CHEBI:59897

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:473990`	entecavir (anhydrous)	`antibioticmech:chebi-1338f90b8a`	2026-08-30

Mechanism summary

Mode of action: VIRAL_POLYMERASE_INHIBITION host shared target — Assigned from ChEBI role CHEBI:59897 (EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — 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.