callophycoic acid A

CHEBI:65557 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A dibenzooxepine diterpenoid that is hexahydrodibenzo[b,e]oxepine with an isolated double bond between positions 6a and 7 and is substituted by a bromo, a carboxy, a 3E-4,8-dimethylnona-3,7-dien-1-yl and a methyl group at positions 9, 2, 10 and 10 respectively (the 9S,10S,10aR stereoisomer). It is isolated from the Fijian red alga Callophycus serratus and exhibits antibacterial, antimalarial and anticancer activities. — 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.

Label unavailable CHEBI:22723
Label unavailable CHEBI:23849
Label unavailable CHEBI:37141
Label unavailable CHEBI:37407
Label unavailable CHEBI:38926

Chemical structure

Computed structure properties
Molecular formula	C27H35BrO3
Charge	0
Average mass	487.478 Da
Monoisotopic mass	486.17696 Da
Source	ChEBI
InChIKey	UWOQPCLHJDMFFV-FXSXARLRSA-N

SMILES

[H][C@@]12Cc3cc(C(=O)O)ccc3OCC1=CC[C@H](Br)[C@@]2(C)CC/C=C(\C)CCC=C(C)C

InChI

InChI=1S/C27H35BrO3/c1-18(2)7-5-8-19(3)9-6-14-27(4)23-16-22-15-20(26(29)30)10-12-24(22)31-17-21(23)11-13-25(27)28/h7,9-12,15,23,25H,5-6,8,13-14,16-17H2,1-4H3,(H,29,30)/b19-9+/t23-,25+,27+/m1/s1

Also called

(9S,10S,10aR)-9-bromo-10-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-10-methyl-6,8,9,10,10a,11-hexahydrodibenzo[b,e]oxepine-2-carboxylic acid (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.

chemspider:23076452
reaxys:11167771

Activity roles

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

antibacterial agent CHEBI:33282
antimalarial CHEBI:38068

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:65557`	callophycoic acid A	`antibioticmech:chebi-1a5d2ad916`	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 (YAML).

Explore across X-Mech: MediaIngredientMech (callophycoic acid A) · CultureMech · NaturalProductMech · PathwayMech · TraitMech