methacycline

CHEBI:6805 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A tetracycline that is the 6-methylene analogue of oxytetracycline, obtained by formal dehydration at position 6. — 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:139592 CHEBI:139592
CHEBI:140324 CHEBI:140324
CHEBI:26895 CHEBI:26895

Chemical structure

Computed structure properties
Molecular formula	C22H22N2O8
Charge	0
Average mass	442.424 Da
Monoisotopic mass	442.13762 Da
Source	ChEBI
InChIKey	MHIGBKBJSQVXNH-IWVLMIASSA-N

SMILES

[H][C@@]12C(=C)c3cccc(O)c3C(=O)C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@]1([H])[C@H]2O

InChI

InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31)/t10-,14-,15+,17+,22+/m1/s1

Also called

metaciclina (INN)— chebi
metacycline (INN)— chebi
metacyclinum (INN)— chebi
(4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide (EXACT_SYNONYM)— chebi
6-Demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline (EXACT_SYNONYM)— chebi
6-Deoxy-6-demethyl-6-methylene-5-oxytetracycline (EXACT_SYNONYM)— chebi
6-Methylene-5-hydroxytetracycline (EXACT_SYNONYM)— chebi
6-Methylene-5-oxytetracycline (EXACT_SYNONYM)— chebi
6-Methyleneoxytetracycline (EXACT_SYNONYM)— chebi
Methacyclinum (EXACT_SYNONYM)— chebi
Methylenecycline (EXACT_SYNONYM)— chebi
Rondomycin (EXACT_SYNONYM)— chebi
Tri-methacycline (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:914-00-1
drugbank:DB00931
drugcentral:1727
kegg.compound:C07654
kegg.drug:D04972
patent:US2984686
reaxys:2230316
wikipedia.en:Methacycline

Activity roles

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

CHEBI:36047 CHEBI:36047

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:6805`	methacycline	`antibioticmech:chebi-8a2a0e734a`	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.