bleomycin A2

CHEBI:3139 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Bleomycin A2 is a glycopeptide antibiotic produced by Streptomyces verticillus taken as a mixture of bleomycins. It induces stand breaks in bacterial nucleic acids. — PMID:15700963

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

glycopeptide antibioticARO:3000081

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:22907 CHEBI:22907
ARO:3000081 ARO:3000081

Chemical structure

Computed structure properties
Molecular formula	C55H84N17O21S3
Charge	1
Average mass	1415.576 Da
Monoisotopic mass	1414.51843 Da
Source	ChEBI
InChIKey	OYVAGSVQBOHSSS-UAPAGMARSA-O

SMILES

[H][C@](C)(NC(=O)[C@@]([H])(NC(=O)c1nc([C@H](CC(N)=O)NC[C@H](N)C(N)=O)nc(N)c1C)[C@@]([H])(O[C@@H]1O[C@@H](CO)[C@@H](O)[C@H](O)[C@@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](OC(N)=O)[C@@H]1O)c1cncn1)[C@@H](O)[C@H](C)C(=O)N[C@]([H])(C(=O)NCCc1nc(-c2nc(C(=O)NCCC[S+](C)C)cs2)cs1)[C@@]([H])(C)O

InChI

InChI=1S/C55H83N17O21S3/c1-20-33(69-46(72-44(20)58)25(12-31(57)76)64-13-24(56)45(59)82)50(86)71-35(41(26-14-61-19-65-26)91-54-43(39(80)37(78)29(15-73)90-54)92-53-40(81)42(93-55(60)88)38(79)30(16-74)89-53)51(87)66-22(3)36(77)21(2)47(83)70-34(23(4)75)49(85)63-10-8-32-67-28(18-94-32)52-68-27(17-95-52)48(84)62-9-7-11-96(5)6/h14,17-19,21-25,29-30,34-43,53-54,64,73-75,77-81H,7-13,15-16,56H2,1-6H3,(H13-,57,58,59,60,61,62,63,65,66,69,70,71,72,76,82,83,84,85,86,87,88)/p+1/t21-,22+,23+,24-,25-,29-,30+,34-,35-,36-,37+,38+,39-,40-,41-,42-,43-,53+,54-/m0/s1

Also called

(βR)-Nα-{[6-amino-2-((1S)-3-amino-1-{[(2S)-2,3-diamino-3-oxopropyl]amino}-3-oxopropyl)-5-methylpyrimidin-4-yl]carbonyl}-β-{2-O-[3-O-(aminocarbonyl)-α-D-mannopyranosyl]-α-L-gulopyranosyloxy}-N-[(1R,2S,3S)-5-({(1S,2R)-1-[({2-[4-({[3-(dimethylsulfonio)propyl]amino}carbonyl)-2,4'-bi-1,3-thiazol-2'-yl]ethyl}amino)carbonyl]-2-hydroxypropyl}amino)-3-hydroxy-4-methyl-5-oxopentan-2-yl]-L-histidinamide (EXACT_SYNONYM)— chebi
BLEOMYCIN A2 (EXACT_SYNONYM)— chebi
Bleomycin (EXACT_SYNONYM)— chebi
Bleomycin A2 (EXACT_SYNONYM)— chebi
N1-[3-(dimethylsulfonio)propyl]bleomycinamide (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000691
beilstein:4379083
cas:11056-06-7
cas:11116-31-7
gmelin:1667354
kegg.compound:C06854
kegg.compound:C15773
kegg.drug:D07535
knapsack:C00018738
pdb-ccd:BLM
wikipedia.en:Bleomycin
pubchem.compound:5460769

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:3000691`	bleomycin A2	`antibioticmech:aro-5336dc6d49`	2026-08-30
CHEBI	`CHEBI:3139`	bleomycin A2	`antibioticmech:chebi-9d72e8f169`	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.

deoxyribonucleic acid NUCLEIC_ACID ATTACKED_COMPONENT

ARO:3000738

CARD/ARO database assertion; target organism, strain, and assay are not specified. ARO describes DNA strand damage or transcription interference. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000738 (CARD/ARO asserts targeted_by_antibiotic ARO:3000691 (bleomycin A2); database assertion, not a primary citation.)

ribonucleic acid NUCLEIC_ACID ATTACKED_COMPONENT

ARO:3000740

CARD/ARO database assertion; target organism, strain, and assay are not specified. ARO describes RNA strand damage across multiple RNA types. Evidence status: DATABASE_ASSERTION_ONLY. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000740 (CARD/ARO asserts targeted_by_antibiotic ARO:3000691 (bleomycin A2); database assertion, not a primary citation.)

Resistance mechanisms

1 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_INACTIVATION 1

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
BRP(MBL)	ARO:3001205	not organism-specific	—	ARO:3001205 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000691 (bleomycin A2); 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.