coumermycin A1

CHEBI:3907 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A hydroxycoumarin antibiotic that is obtained from Streptomyces rishiriensis and exhibits potent antibacterial and anticancer activity. — 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

aminocoumarin antibioticARO:3000103

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:23403 CHEBI:23403
CHEBI:24400 CHEBI:24400
CHEBI:26455 CHEBI:26455
CHEBI:38064 CHEBI:38064
CHEBI:62733 CHEBI:62733
ARO:3000103 ARO:3000103

Chemical structure

Computed structure properties
Molecular formula	C55H59N5O20
Charge	0
Average mass	1110.092 Da
Monoisotopic mass	1109.37534 Da
Source	ChEBI
InChIKey	WTIJXIZOODAMJT-DHFGXMAYSA-N

SMILES

CO[C@@H]1[C@@H](OC(=O)c2ccc(C)n2)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4cnc(C(=O)Nc5c(O)c6ccc(O[C@@H]7OC(C)(C)[C@H](OC)[C@@H](OC(=O)c8ccc(C)n8)[C@H]7O)c(C)c6oc5=O)c4C)c(=O)oc3c2C)OC1(C)C

InChI

InChI=1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1

Also called

coumamycine (INN)— chebi
coumamycinum (INN)— chebi
cumamicina (INN)— chebi
(3-methyl-1H-pyrrole-2,4-diyl)bis[carbonylimino(4-hydroxy-8-methyl-2-oxo-2H-chromene-3,7-diyl)oxy(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2,4-diyl] bis(5-methyl-1H-pyrrole-2-carboxylate) (EXACT_SYNONYM)— chebi
Coumermycin (EXACT_SYNONYM)— chebi
NSC 107412 (EXACT_SYNONYM)— chebi
Notomycin (EXACT_SYNONYM)— chebi
Notomycin A1 (EXACT_SYNONYM)— chebi
Sugordomycin D-1a (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000150
cas:4434-05-3
kegg.compound:C05073
kegg.drug:D02333
knapsack:C00002461
reaxys:5230975
wikipedia.en:Coumermycin_A1
chembl:CHEMBL389471
pubchem.compound:54675768

Activity roles

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

CHEBI:33281 CHEBI:33281

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:3000150`	coumermycin A1	`antibioticmech:aro-cc3947c3d9`	2026-08-30
CHEBI	`CHEBI:3907`	coumermycin A1	`antibioticmech:chebi-977895c932`	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.

aminocoumarin sensitive parE PROTEIN DIRECT_BINDING_TARGET

ARO:3000023

CARD/ARO database assertion; target organism, strain, and assay are not specified. Topoisomerase IV subunit asserted as the aminocoumarin-sensitive target. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000023 (CARD/ARO asserts targeted_by_antibiotic ARO:3000150 (coumermycin A1); database assertion, not a primary citation.)

antibiotic sensitive DNA topoisomerase subunit gyrB PROTEIN DIRECT_BINDING_TARGET

ARO:3000734

CARD/ARO database assertion; target organism, strain, and assay are not specified. ARO explicitly describes ligand binding to gyrase subunit B. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000734 (CARD/ARO asserts targeted_by_antibiotic ARO:3000150 (coumermycin A1); database assertion, not a primary citation.)

aminocoumarin sensitive parY PROTEIN DIRECT_BINDING_TARGET

ARO:3003253

CARD/ARO database assertion; target organism, strain, and assay are not specified. ParY is asserted as the aminocoumarin-sensitive subunit. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3003253 (CARD/ARO asserts targeted_by_antibiotic ARO:3000150 (coumermycin A1); database assertion, not a primary citation.)

aminocoumarin sensitive gyrB PROTEIN DIRECT_BINDING_TARGET

ARO:3003260

CARD/ARO database assertion; target organism, strain, and assay are not specified. GyrB is asserted as the aminocoumarin-sensitive subunit. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3003260 (CARD/ARO asserts targeted_by_antibiotic ARO:3000150 (coumermycin A1); database assertion, not a primary citation.)

Mechanism summary

Mode of action: NUCLEIC_ACID_SYNTHESIS_INHIBITION microbial target — Assigned from ChEBI role CHEBI:53559 (topoisomerase IV inhibitor), CHEBI:59517 (DNA synthesis 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.

Resistance mechanisms

5 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 5

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Bartonella bacilliformis gyrB conferring resistance to aminocoumarin	ARO:3003302	not organism-specific	—	ARO:3003302 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000150 (coumermycin A1); database assertion, not a primary citation.)
Escherichia coli gyrB conferring resistance to aminocoumarin	ARO:3003303	not organism-specific	—	ARO:3003303 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000150 (coumermycin A1); database assertion, not a primary citation.)
Staphylococcus aureus gyrB conferring resistance to aminocoumarin	ARO:3003301	not organism-specific	—	ARO:3003301 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000150 (coumermycin A1); database assertion, not a primary citation.)
Staphylococcus aureus parE conferring resistance to aminocoumarin	ARO:3003314	not organism-specific	—	ARO:3003314 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000150 (coumermycin A1); database assertion, not a primary citation.)
Streptomyces rishiriensis parY mutant conferring resistance to aminocoumarin	ARO:3003318	not organism-specific	—	ARO:3003318 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000150 (coumermycin A1); 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

Provenance

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