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.

CHEBI:25105 CHEBI:25105
CHEBI:26177 CHEBI:26177
CHEBI:87113 CHEBI:87113
ARO:3007497 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

Equivalent identifiers for this same structure in other resources.

ARO:3007504
cas:1397-89-3
drugbank:DB00681
drugcentral:197
kegg.compound:C06573
kegg.drug:D00203
lipidmaps:LMPK06000002
patent:US2908611
reaxys:4645978
wikipedia.en:Amphotericin_B
chembl:CHEMBL267345
pubchem.compound:5280965

Activity roles

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

CHEBI:33281 CHEBI:33281
CHEBI:35718 CHEBI:35718
CHEBI:35820 CHEBI:35820
CHEBI:86327 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 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

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

Provenance

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