chlortetracycline

CHEBI:27644 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A member of the class of tetracyclines with formula C22H23ClN2O8 isolated from Streptomyces aureofaciens. — 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

tetracycline antibioticARO:3000050

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:139592 CHEBI:139592
CHEBI:26878 CHEBI:26878
CHEBI:26895 CHEBI:26895
CHEBI:29347 CHEBI:29347
CHEBI:50996 CHEBI:50996
CHEBI:83403 CHEBI:83403
ARO:3000050 ARO:3000050

Chemical structure

Computed structure properties
Molecular formula	C22H23ClN2O8
Charge	0
Average mass	478.885 Da
Monoisotopic mass	478.11429 Da
Source	ChEBI
InChIKey	CYDMQBQPVICBEU-XRNKAMNCSA-N

SMILES

[H][C@]12C[C@@]3([H])[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]3(O)C(O)=C1C(=O)c1c(O)ccc(Cl)c1[C@@]2(C)O

InChI

InChI=1S/C22H23ClN2O8/c1-21(32)7-6-8-15(25(2)3)17(28)13(20(24)31)19(30)22(8,33)18(29)11(7)16(27)12-10(26)5-4-9(23)14(12)21/h4-5,7-8,15,26,28-29,32-33H,6H2,1-3H3,(H2,24,31)/t7-,8-,15-,21-,22-/m0/s1

Also called

Aueromycin (BRAND_NAME)— chebi
chlortetracyclinum (INN)— chebi
chlortétracycline (INN)— chebi
clortetraciclina (INN)— chebi
(4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide (EXACT_SYNONYM)— chebi
7-Chlorotetracycline (EXACT_SYNONYM)— chebi
Aureomycin (EXACT_SYNONYM)— aro
Eremomycine (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000528
cas:57-62-5
drugcentral:624
hmdb:HMDB0014401
kegg.compound:C06571
kegg.drug:D07689
lipidmaps:LMPK07000004
patent:US2482055
pdb-ccd:CTC
chembl:CHEMBL404520
pubchem.compound:54675777

Activity roles

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

CHEBI:35820 CHEBI:35820
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
ARO	`ARO:3000528`	chlortetracycline	`antibioticmech:aro-c48086099a`	2026-08-30
CHEBI	`CHEBI:27644`	chlortetracycline	`antibioticmech:chebi-fe26d2566d`	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.

antibiotic sensitive 16S rRNA NUCLEIC_ACID DIRECT_BINDING_TARGET

ARO:3000755

CARD/ARO database assertion; target organism, strain, and assay are not specified. 16S rRNA is asserted as the target. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000755 (CARD/ARO asserts targeted_by_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)

Resistance mechanisms

15 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_TARGET_PROTECTION 11

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
tet(32)	ARO:3000196	not organism-specific	—	ARO:3000196 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)
tet(36)	ARO:3000197	not organism-specific	—	ARO:3000197 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)
tet(44)	ARO:3000556	not organism-specific	—	ARO:3000556 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)
tet(M)	ARO:3000186	not organism-specific	—	ARO:3000186 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)
tet(O)	ARO:3000190	not organism-specific	—	ARO:3000190 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)
tet(Q)	ARO:3000191	not organism-specific	—	ARO:3000191 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)
tet(S)	ARO:3000192	not organism-specific	—	ARO:3000192 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)
tet(T)	ARO:3000193	not organism-specific	—	ARO:3000193 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)
tet(W)	ARO:3000194	not organism-specific	—	ARO:3000194 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)
tet(W/N/W)	ARO:3004442	not organism-specific	—	ARO:3004442 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)
tetB(P)	ARO:3000195	not organism-specific	—	ARO:3000195 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 2

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
lmrP	ARO:3003969	not organism-specific	—	ARO:3003969 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)
tet(59)	ARO:3004441	not organism-specific	—	ARO:3004441 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)

ANTIBIOTIC_INACTIVATION 1

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
tet(X)	ARO:3000205	not organism-specific	—	ARO:3000205 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 1

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
Escherichia coli LamB	ARO:3004126	not organism-specific	—	ARO:3004126 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000528 (chlortetracycline); 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.