exophillic acid

CHEBI:232062 ·resolve ·ANTIVIRAL ·EXACT REVIEWED

A monosaccharide derivative that is 4-(2,4-dihydroxy-6-nonylbenzoyloxy)-2-hydroxy-6-nonylbenzoic acid in which the hydroxy group at position 2 is replaced by a β-D-glucopyranosyloxy group. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:22798
Label unavailable CHEBI:25389
Label unavailable CHEBI:33853
Label unavailable CHEBI:36054
Label unavailable CHEBI:63367

Chemical structure

Computed structure properties
Molecular formula	C38H56O12
Charge	0
Average mass	704.854 Da
Monoisotopic mass	704.37718 Da
Source	ChEBI
InChIKey	GBXMNTLQBMLGFM-IHQQTPIISA-N

SMILES

CCCCCCCCCc1cc(OC(=O)c2c(CCCCCCCCC)cc(O)cc2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc(O)c1C(=O)O

InChI

InChI=1S/C38H56O12/c1-3-5-7-9-11-13-15-17-24-19-26(40)21-29(49-38-35(44)34(43)33(42)30(23-39)50-38)32(24)37(47)48-27-20-25(31(36(45)46)28(41)22-27)18-16-14-12-10-8-6-4-2/h19-22,30,33-35,38-44H,3-18,23H2,1-2H3,(H,45,46)/t30-,33-,34+,35-,38-/m1/s1

Also called

4-{[2-(β-D-glucopyranosyloxy)-4-hydroxy-6-nonylbenzoyl]oxy}-2-hydroxy-6-nonylbenzoic acid (EXACT_SYNONYM)— chebi
4-(2-β-D-glucopyranosyloxy-4-hydroxy-6-nonylbenzoyloxy)-2-hydroxy-6-nonylbenzoic acid (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Activity roles

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

anti-HBV agent CHEBI:64951

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:232062`	exophillic acid	`antibioticmech:chebi-43f23c9539`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

HIV-1 integrase strand-transfer activity VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

An in-vitro HIV-1 integrase strand-transfer assay measured an IC50 of 68 micromolar; direct compound binding was not established. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2003-12 (retrieved 2026-09-02).

Organism-specific examples
Protein	Gene	Organism	Entry
Gag-Pol polyprotein `UniProtKB:P04585` HIV-1 Gag-Pol precursor encoding the integrase enzyme whose strand-transfer activity is inhibited by exophillic acid in vitro (PMID:15015729; HXB2 reference isolate context).	gag-pol	Human immunodeficiency virus type 1 group M subtype B (isolate HXB2) `NCBITaxon:11706`	REVIEWED

PMID:15015729 (Primary isolation, structure-elucidation, and HIV-1 integrase assay study.)

sodium taurocholate cotransporting polypeptide (NTCP) PROTEIN MEASURED_TARGET_ASSOCIATION

Primary human hepatocyte infection, preS1 attachment, bile-acid uptake, and compound-NTCP interaction assays implicated this host HBV/HDV receptor; the abstract does not establish a cocrystal. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2022-04 (retrieved 2026-09-02).

Organism-specific examples
Protein	Gene	Organism	Entry
Sodium/bile acid cotransporter `UniProtKB:Q14973` Human hepatocyte sodium/bile acid cotransporter (NTCP) host entry receptor bound by exophillic acid to block HBV and HDV preS1-mediated viral attachment (PMID:35458494).	SLC10A1	Homo sapiens `NCBITaxon:9606`	REVIEWED

PMID:35458494 (Primary HBV/HDV entry and host-receptor mechanism study (DOI:10.3390/v14040764).)

Mechanism summary

Mode of action: MULTIPLE — CURATOR: exophillic acid has two compound-specific antiviral mechanisms in different systems. PMID:15015729 measured inhibition of HIV-1 integrase strand transfer (IC50 68 micromolar), whereas PMID:35458494 found that it interacts with host NTCP and blocks preS1-mediated attachment and entry of HBV and HDV without affecting intracellular HBV replication. The mixed viral and host targets make a single target-scope value inappropriate.

Record-level evidence

PMID:15015729 (Primary isolation and HIV-1 integrase assay report.)
PMID:35458494 (Primary HBV/HDV entry mechanism study.)

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
REVIEWED 2026-09-02 · codex · LLM-assisted
Verified exact ChEBI identity, structure, and antiviral class; added the distinct HIV-integrase and host-NTCP entry mechanisms, used MULTIPLE for their coexistence, and deliberately omitted a misleading single scope.
CURATED_UNIPROT_PROTEIN_EXAMPLES 2026-10-18 · antigravity · LLM-assisted
Added curated HIV-1 HXB2 Gag-Pol polyprotein (P04585) and human host SLC10A1/NTCP (Q14973) UniProtKB protein examples on the two PRIMARY_LITERATURE molecular targets of exophillic acid.

Provenance

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

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