Doxycycline

Athanor · official

C₂₂H₂₄N₂O₈ · 444.4 g/mol

IUPAC name: 4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide

Also called Vibramycin, Doryx, tetracycline

Drugs Natural products

Open in Athanor

Drawn from its SMILES with RDKit

Names and identifiers

IUPAC name: 4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
Synonyms: Vibramycin, Doryx, tetracycline
+ 37 more
4-Epi-6-epi Doxycycline, 4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide, Liviatin, 2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,10,11,12a-tetrahydroxy-6-methyl-1,2,3,4,4a,5,5a,6,12,12a-decahydrotetracene-1,3,12-trione, 2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, 4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide, .alpha.-6-Deoxyoxytetracycline, SCHEMBL2614979, SCHEMBL4082631, SCHEMBL4082642, CHEMBL3559889, CHEMBL4586670, SCHEMBL29370610, SCHEMBL29388088, JBIWCJUYHHGXTC-UHFFFAOYSA-N, HMS3259F03, HMS5084B11, 6-.alpha.-Deoxy-5-oxytetracycline, BBL013212, MFCD01970950, s5159, STK177208, AKOS005410764, .alpha.-6-Deoxy-5-hydroxytetracycline, 5-Hydroxy-.alpha.-6-deoxytetracycline, NC00609, PD003014, PD055377, VS-03707, DB-052915, NS00000694, EN300-49866, 2-(amino-hydroxy-methylidene)-4-dimethylamino-5,10,11,12a-tetrahydroxy-6-methyl-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione, 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, [4S-(4.alpha.,4a.alpha.,5.alpha.,5, 2-Naphthacenecarboxamide, 4-.alpha.-S-(dimethylamino)-1,4,4a-.alpha.-5,5a-.alpha.,6,11,12a-octahydro-3,5-.alpha.,10,12,12a-.alpha.-pentahydroxy-6-.alpha.-methyl-1,11-dioxo-, 4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide, 4-dimethylamino-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacencarboxamid
Molecular formula: C₂₂H₂₄N₂O₈
Empirical formula: C₁₁H₁₂NO₄
Molecular weight: 444.4 g/mol
Exact mass: 444.15327
CAS number: 564-25-0
PubChem CID: 54681536
Canonical SMILES: CC1C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
Isomeric SMILES: CC1C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
InChI: InChI=1S/C22H24N2O8/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/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)
InChIKey: SGKRLCUYIXIAHR-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms: 32
Rings: 4
Aromatic rings: 1
Fraction sp³ carbons (Fsp3): 0.41
H-bond donors: 6
H-bond acceptors: 9
Rotatable bonds: 2
TPSA (Å²): 181.6 computed here · PubChem 182
Formal charge: 0
XLogP3: -0.7 PubChem
Complexity: 956 PubChem
Stereocenters: 0 defined, 6 undefinedCIP: C4: undefined · C5: undefined · C6: undefined · C8: undefined · C19: undefined · C23: undefined
Double-bond geometry: None specified
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C59.46%
H5.44%
N6.30%
O28.80%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: -0.5 Crippen (Wildman and Crippen 1999)
log S (water solubility): -2.28 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 4.48 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 444.44
log P ≤ 5 (Crippen): -0.5
H-bond donors ≤ 5: 6
H-bond acceptors ≤ 10: 9

Breaks 1 of the four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

No GHS hazard classification was found in the sources.

Safety data sheets on the supplier’s page: Vitas-M Laboratory, Molport, A2B Chem.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
[2]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[3]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.