nocamycin I

CHEBI:138066 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

An organic heterotricyclic compound and tetramic acid derivative originally isolated from an unidentified oligosporic actinomycete strain (no. E864-861) and found to be active against both Gram-positive and Gram-negative anaerobic bacteria as well as some aerobic bacteria such as Streptococci. The methyl ester of nocamycin E. — 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

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:140155 CHEBI:140155
CHEBI:25248 CHEBI:25248
CHEBI:26979 CHEBI:26979
CHEBI:33823 CHEBI:33823
CHEBI:72600 CHEBI:72600
CHEBI:74222 CHEBI:74222
CHEBI:78840 CHEBI:78840

Chemical structure

Computed structure properties
Molecular formula	C26H33NO9
Charge	0
Average mass	503.548 Da
Monoisotopic mass	503.21553 Da
Source	ChEBI
InChIKey	DTURANKMSHIDDI-GMYASLLUSA-N

SMILES

[H][C@]1([C@H](C)/C=C(C)/C=C/C(O)=C2/C(=O)CNC2=O)O[C@@]23O[C@]([H])(C(=O)C[C@]2(C)O[C@H](C)[C@@H]3C(=O)OC)[C@@H]1C

InChI

InChI=1S/C26H33NO9/c1-12(7-8-16(28)19-18(30)11-27-23(19)31)9-13(2)21-14(3)22-17(29)10-25(5)26(35-21,36-22)20(15(4)34-25)24(32)33-6/h7-9,13-15,20-22,28H,10-11H2,1-6H3,(H,27,31)/b8-7+,12-9+,19-16+/t13-,14-,15-,20-,21-,22+,25+,26+/m1/s1

Also called

methyl (2R,3S,3aS,5R,6R,7S,9aS)-5-[(2R,3E,5E,7E)-7-(2,4-dioxopyrrolidin-3-ylidene)-7-hydroxy-4-methylhepta-3,5-dien-2-yl]-2,6,9a-trimethyl-8-oxooctahydro-3a,7-epoxyfuro[3,2-b]oxocine-3-carboxylate (EXACT_SYNONYM)— chebi
(−)-nocamycin I (EXACT_SYNONYM)— chebi
Antibiotic BU 2313B (EXACT_SYNONYM)— chebi
BU 2313B (EXACT_SYNONYM)— chebi
Bu-2313B (EXACT_SYNONYM)— chebi
methyl (1S,2S,3R,5S,8S,9R,10R)-10-[(2R,3E,5E,7E)-7-(2,4-dioxopyrrolidin-3-ylidene)-7-hydroxy-4-methylhepta-3,5-dien-2-yl]-3,5,9-trimethyl-7-oxo-4,11,12-trioxatricyclo[6.3.1.01,5]dodecane-2-carboxylate (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

metacyc.compound:CPD-18224
patent:US4181574

Activity roles

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

CHEBI:33282 CHEBI:33282

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
CHEBI	`CHEBI:138066`	nocamycin I	`antibioticmech:chebi-16da342cd5`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (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

Provenance

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