Tetracycline 10-O-β-D-galactopyranoside

Key facts

CAS number

319426-63-6

Form

Solid

form

Molecular weight

606.6 Da

Molecular formula

C₂₈H₃₄N₂O₁₃

PubChem

54730589

Nature

Synthetic

Solubility

Soluble in DMSO

Soluble in water

Biochemical name

Tetracycline 10-O-B-D-galactopyranoside

Biological description

Broad spectrum polyketide antibiotic. Produced by Streptomyces genus of Actinobacteria. Acts as a protein synthesis inhibitor and is commonly used to treat acne today, and, more recently, rosacea. Historically important in reducing the number of deaths from cholera. In this galactoside analog, upon enzymatic or chemical hydrolysis of the galactoside group, the active antibiotic tetracyline is produced.

Canonical smiles

CC1(C2CC3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4OC5C(C(C(C(O5)CO)O)O)O)O)O)O)C(=O)N)N(C)C)O

Isomeric smiles

C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)O)O)O)C(=O)N)N(C)C)O

InChi

InChI=1S/C28H34N2O13/c1-27(40)9-5-4-6-12(42-26-22(36)21(35)18(32)13(8-31)43-26)14(9)19(33)15-10(27)7-11-17(30(2)3)20(34)16(25(29)39)24(38)28(11,41)23(15)37/h4-6,10-11,13,17-18,21-22,26,31-33,35-36,38,40-41H,7-8H2,1-3H3,(H2,29,39)/t10-,11-,13+,17-,18-,21-,22+,26+,27+,28-/m0/s1

InChiKey

NQIGPCCKIYYEBO-UCUSNPRGSA-N

IUPAC Name

(4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,11,12a-tetrahydroxy-6-methyl-3,12-dioxo-10-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,5a-tetrahydrotetracene-2-carboxamide