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

Classification

glycopeptide antibioticARO:3000081

Strictly broader compounds or drug classes this molecule belongs to.

• bleomycin CHEBI:22907
• glycopeptide antibiotic ARO:3000081

Chemical structure

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

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.

• bleomycin A2ARO:3000691
• beilstein:4379083
• cas:11056-06-7
• cas:11116-31-7
• gmelin:1667354
• kegg.compound:C06854
• kegg.compound:C15773
• knapsack:C00018738
• pdb-ccd:BLM
• pubchem.compound:5460769

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.

• kegg.drug:D07535

Patents and articles

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

• wikipedia.en:Bleomycin

Activity roles

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

• antimicrobial agent 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.

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

Producer organisms

Organisms that biosynthesize this compound. Cluster link evidence is how the upstream source graded the gene cluster, so it is populated only for a source that grades it. An empty cell is not weaker support: a curator-authored producer carries its support in Evidence instead. Where the source entry named several compounds, the evidence is marked inherited, meaning it covers this compound together with the cluster's other products rather than singling it out. Those products need not be related to each other: a cluster can list an intermediate, a precursor and a finished antibiotic side by side.

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

6. RESEEDED_FROM_SOURCES 2026-09-08 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

7. 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).

Explore across X-Mech: MediaIngredientMech (bleomycin A2) · CultureMech · NaturalProductMech · PathwayMech · TraitMech · TaxonMech (Streptomyces mobaraensis)