Heliquinomycin, Antibiotic agent

Key facts

CAS number

178182-49-5

Purity

>80%

Form

Solid

form

Source

Streptomyces sp.

Molecular weight

698.6 Da

Molecular formula

C₃₃H₃₀O₁₇

PubChem

5470493

Nature

Native

Solubility

Soluble in ethanol

Soluble in DMSO

Biochemical name

Heliquinomycin

Biological description

Antibiotic agent. DNA helicase inhibitor (IC₅₀ values are 4.3 and 2.5 μM for DNA helicase B and MCM4/6/7 helicase respectively). Inhibits DNA replication (IC₅₀ values are 1 - 4 μM). Weak topoisomerase I and II inhibitor. Inhibits DNA and RNA synthesis. Does not inhibit protein synthesis. Induces G2/M cell cycle arrest. Shows antibacterial effects. Inhibits cancer cell line growth (IC₅₀ values are 1.4 - 4 μM).

Canonical smiles

CC1C(C(CC(O1)OC2C3=C(C4=C(C(=C3OC25C(CC6=C(O5)C(=C7C(=C6)C=C(OC7=O)C(=O)OC)O)O)O)C(=O)C(=CC4=O)OC)O)OC)O

Isomeric smiles

CC1C(C(CC(O1)O[C@@H]2C3=C(C4=C(C(=C3O[C@]25[C@@H](CC6=C(O5)C(=C7C(=C6)C=C(OC7=O)C(=O)OC)O)O)O)C(=O)C(=CC4=O)OC)O)OC)O

InChi

InChI=1S/C33H30O17/c1-10-23(36)15(44-3)9-18(46-10)48-30-22-25(38)20-13(34)8-14(43-2)24(37)21(20)27(40)29(22)50-33(30)17(35)7-12-5-11-6-16(31(41)45-4)47-32(42)19(11)26(39)28(12)49-33/h5-6,8,10,15,17-18,23,30,35-36,38-40H,7,9H2,1-4H3/t10?,15?,17-,18?,23?,30-,33-/m1/s1

InChiKey

MLFZQFHGXSVTGX-VJANPNJTSA-N

IUPAC Name

methyl (2R,3R,3'R)-3,4',9',10-tetrahydroxy-3'-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-7'-methoxy-5',8',9-trioxospiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate