neocarzinostatin

Also known as zinostatin

Neocarzinostatin (NCS) is a macromolecular chromoprotein enediyne antitumor antibiotic secreted by Streptomyces macromomyceticus.

Chemical data

Formula: C35H35NO12
Molecular weight: 661.6 g/mol
IUPAC name: [(4S,11R,12R)-11-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-methyl-3-(methylamino)oxan-2-yl]oxy-4-(2-oxo-1,3-dioxolan-4-yl)-5-oxatricyclo[8.3.0.04,6]tridec-1(13)-en-2,7-diyn-12-yl] 2-hydroxy-7-methoxy-5-methylnaphthalene-1-carboxylate
SMILES: C[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)O[C@H]2[C@@H](C=C3C2CC#CC4[C@@](O4)(C#C3)C5COC(=O)O5)OC(=O)C6=C(C=CC7=C6C=C(C=C7C)OC)O)NC)O)O
InChIKey: BLXZMHNVKCEIJX-LTZUVELHSA-N
XLogP: 2.3
Polar surface area: 175 Å²
H-bond donors: 4
H-bond acceptors: 13
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Mass: 661.216

Show 5 more facts

canonical SMILES: CC1C(C(C(C(O1)OC2C3CC#CC4C(O4)(C#CC3=CC2OC(=O)C5=C(C=CC6=C(C=C(C=C65)OC)C)O)C7COC(=O)O7)NC)O)O
subject has role: DNA polymerase inhibitors
chemical formula: C₃₅H₃₅NO₁₂
isomeric SMILES: C[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)O[C@H]2[C@@H](C=C3C2CC#CC4[C@@](O4)(C#C3)C5COC(=O)O5)OC(=O)C6=C(C=CC7=C(C=C(C=C76)OC)C)O)NC)O)O
Commons category: Neocarzinostatin

Sources (3)

via Wikidata · CC0

~4 min read

Encyclopedic overview

2 sections

Contents

Biosynthesis of NCS Chromophore
References

{{Chembox |Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 441386715 |Reference = |Name = Neocarzinostatin chromophore |ImageFile = Neocarzinostatin.png |ImageAlt = Structural formula of neocarzinostatin |ImageFile1 = Neocarzinostatin 3D spacefill.png |ImageAlt1 = Space-filling model of the neocarzinostatin molecule |IUPACName = (1aS,5R,6R,6aE)-6-{[(2R,3R,4R,5R,6R)-4,5-Dihydroxy-6-methyl-3-(methylamino)tetrahydro-2H-pyran-2-yl]oxy}-1a-(2-oxo-1,3-dioxolan-4-yl)-2,3,8,9-tetradehydro-1a,5,6,9a-tetrahydrocyclopenta[5,6]cyclonona[1,2-b]oxiren-5-yl 2-hydroxy-7-methoxy-5-methyl-1-naphthoate |Section1= |Section2= |Section5= }}

Neocarzinostatin (NCS) is a macromolecular chromoprotein enediyne antitumor antibiotic secreted by Streptomyces macromomyceticus.

Excerpted from Wikipedia’s “neocarzinostatin” article, available under the CC BY-SA 4.0 licence.