oxytetracycline

CHEBI:27701 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A tetracycline used for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae. — 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:26895 CHEBI:26895
ARO:3000050 ARO:3000050

Chemical structure

Computed structure properties
Molecular formula	C22H24N2O9
Charge	0
Average mass	460.439 Da
Monoisotopic mass	460.14818 Da
Source	ChEBI
InChIKey	IWVCMVBTMGNXQD-PXOLEDIWSA-N

SMILES

[H][C@@]12[C@@H](O)[C@@]3([H])C(=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C)C(=O)c1c(O)cccc1[C@@]3(C)O

InChI

InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1

Also called

oxitetraciclina (INN)— chebi
oxytetracyclinum (INN)— chebi
(4S,4aR,5S,5aR,6S,12aS)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide (EXACT_SYNONYM)— chebi
5-Hydroxytetracycline (EXACT_SYNONYM)— chebi
Oxyterracin (EXACT_SYNONYM)— chebi
Oxyterracine (EXACT_SYNONYM)— chebi
Oxytetracyclin (EXACT_SYNONYM)— chebi
Oxytetracycline (anhydrous) (EXACT_SYNONYM)— chebi
Oxytetracycline amphoteric (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000668
beilstein:2686362
bpdb:503
cas:79-57-2
drugbank:DB00595
drugcentral:2041
gmelin:623487
hmdb:HMDB0014733
kegg.compound:C06624
knapsack:C00017127
lipidmaps:LMPK07000005
pesticides:oxytetracycline
reaxys:2714587
vsdb:503
wikipedia.en:Oxytetracycline
chembl:CHEMBL1517
pubchem.compound:54675779

Activity roles

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

CHEBI:33281 CHEBI:33281
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:3000668`	oxytetracycline	`antibioticmech:aro-c765f0a671`	2026-08-30
CHEBI	`CHEBI:27701`	oxytetracycline	`antibioticmech:chebi-ae58abf0ce`	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:3000668 (oxytetracycline); database assertion, not a primary citation.)

Mechanism summary

Mode of action: PROTEIN_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:48001 (protein synthesis inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Resistance mechanisms

29 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_INACTIVATION 14

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
tet(47)	ARO:3004613	not organism-specific	—	ARO:3004613 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(48)	ARO:3004581	not organism-specific	—	ARO:3004581 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(49)	ARO:3004582	not organism-specific	—	ARO:3004582 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(50)	ARO:3004584	not organism-specific	—	ARO:3004584 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(51)	ARO:3004586	not organism-specific	—	ARO:3004586 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(52)	ARO:3004587	not organism-specific	—	ARO:3004587 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(53)	ARO:3004589	not organism-specific	—	ARO:3004589 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(54)	ARO:3004590	not organism-specific	—	ARO:3004590 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(55)	ARO:3004591	not organism-specific	—	ARO:3004591 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(56)	ARO:3004603	not organism-specific	—	ARO:3004603 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(X)	ARO:3000205	not organism-specific	—	ARO:3000205 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(X1)	ARO:3005166	not organism-specific	—	ARO:3005166 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(X5)	ARO:3005057	not organism-specific	—	ARO:3005057 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(X6)	ARO:3005056	not organism-specific	—	ARO:3005056 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_PROTECTION 11

ANTIBIOTIC_TARGET_PROTECTION
Determinant	ARO ID	Organism	Gene families	Evidence
Streptomyces rimosus otr(A)	ARO:3002891	not organism-specific	—	ARO:3002891 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(32)	ARO:3000196	not organism-specific	—	ARO:3000196 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(36)	ARO:3000197	not organism-specific	—	ARO:3000197 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(44)	ARO:3000556	not organism-specific	—	ARO:3000556 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(M)	ARO:3000186	not organism-specific	—	ARO:3000186 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(O)	ARO:3000190	not organism-specific	—	ARO:3000190 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(Q)	ARO:3000191	not organism-specific	—	ARO:3000191 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(S)	ARO:3000192	not organism-specific	—	ARO:3000192 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(T)	ARO:3000193	not organism-specific	—	ARO:3000193 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(W)	ARO:3000194	not organism-specific	—	ARO:3000194 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tetB(P)	ARO:3000195	not organism-specific	—	ARO:3000195 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 4

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Corynebacterium striatum tetA	ARO:3004639	not organism-specific	—	ARO:3004639 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
lmrP	ARO:3003969	not organism-specific	—	ARO:3003969 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
mef(C)	ARO:3003745	not organism-specific	—	ARO:3003745 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); database assertion, not a primary citation.)
tet(59)	ARO:3004441	not organism-specific	—	ARO:3004441 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000668 (oxytetracycline); 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.