amphotericin B

CHEBI:2682 ·resolve ·ANTIFUNGAL ·EXACT SEEDED

A macrolide antibiotic used to treat potentially life-threatening fungal infections. — 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

polyene antifungalARO:3007497

Strictly broader compounds or drug classes this molecule belongs to.

macrolide antibiotic CHEBI:25105
polyene antibiotic CHEBI:26177
antibiotic antifungal drug CHEBI:87113
polyene antifungal ARO:3007497

Chemical structure

Computed structure properties
Molecular formula	C47H73NO17
Charge	0
Average mass	924.091 Da
Monoisotopic mass	923.48785 Da
Source	ChEBI
InChIKey	APKFDSVGJQXUKY-INPOYWNPSA-N

SMILES

[H][C@]12C[C@@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@H](N)[C@@H]3O)/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]1C(=O)O)O2

InChI

InChI=1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1

Also called

amfotericina B (INN)— chebi
amphotericine B (INN)— chebi
amphotericinum B (INN)— chebi
(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-[(3-amino-3,6-dideoxy-β-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid (EXACT_SYNONYM)— chebi
AMPH-B (EXACT_SYNONYM)— chebi
Amphotericine B (EXACT_SYNONYM)— chebi
Liposomal Amphotericin B (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.

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

antimicrobial agent CHEBI:33281
antifungal agent CHEBI:35718
antiprotozoal drug CHEBI:35820
antifungal drug CHEBI:86327

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
ARO	`ARO:3007504`	amphotericin B	`antibioticmech:aro-473ef1d757`	2026-08-30
CHEBI	`CHEBI:2682`	amphotericin B	`antibioticmech:chebi-1637b095ef`	2026-08-30

Mechanism summary

Clinical status: APPROVED

Resistance mechanisms

3 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_TARGET_ALTERATION 3

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Aspergillus fumigatus cyp51a with mutations conferring resistance to amphotericin B	ARO:3009209	not organism-specific	—	ARO:3009209 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007504 (amphotericin B); database assertion, not a primary citation.)
Candida auris ERG11 lanosterol 14-alpha-demethylase with mutations conferring resistance against amphotericin B	ARO:3009394	not organism-specific	—	ARO:3009394 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007504 (amphotericin B); database assertion, not a primary citation.)
antifungal resistance-associated MSH	ARO:3009134	not organism-specific	—	ARO:3009134 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3007504 (amphotericin B); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, 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
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · 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 (YAML).

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