phleomycin D1

Also known as Zeocin

Zeocin is a trade name for a formulation of phleomycin D1, a glycopeptide antibiotic and one of the phleomycins from Streptomyces verticillus belonging to the bleomycin family of antibiotics. It is a broad-spectrum antibiotic that is effective against most aerobic organisms including bacteria, filamentous fungi, yeast, plant, and animal cells. It causes cell death by intercalating into DNA and inducing double stranded breaks of the DNA.

In the Vinony graph

Within Vinony's link graph, phleomycin D1 is referenced by 4 other articles, and connects out to digital object identifier, chemical formula and molar mass.

Vinony files it under Chembox image size set, Eukaryotic selection compounds and Glycopeptide antibiotics.

Its subject is documented across 8 Wikipedia language editions.

Chemical data

Formula: C55H86N20O21S2
Molecular weight: 1427.5 g/mol
IUPAC name: [(2R,3S,4S,5R,6R)-2-[(2R,3S,4S,5S,6S)-2-[(1R,2S)-2-[[6-amino-2-[(1S)-3-amino-1-[[(2S)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[[(2R,3S,4S)-5-[[(2S,3R)-1-[2-[(4R)-4-[4-[4-(diaminomethylideneamino)butylcarbamoyl]-1,3-thiazol-2-yl]-4,5-dihydro-1,3-thiazol-2-yl]ethylamino]-3-hydroxy-1-oxobutan-2-yl]amino]-3-hydroxy-4-methyl-5-oxopentan-2-yl]amino]-1-(1H-imidazol-5-yl)-3-oxopropoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl] carbamate
SMILES: CC1=C(N=C(N=C1N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)C(=O)N[C@@H]([C@H](C2=CN=CN2)O[C@H]3[C@H]([C@H]([C@@H]([C@@H](O3)CO)O)O)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)OC(=O)N)O)C(=O)N[C@H](C)[C@H]([C@H](C)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCCC5=N[C@H](CS5)C6=NC(=CS6)C(=O)NCCCCN=C(N)N)O
InChIKey: CWCMIVBLVUHDHK-ZSNHEYEWSA-N
XLogP: -10.3
Polar surface area: 744 Å²
H-bond donors: 22
H-bond acceptors: 32
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Mass: 1426.571782

Show 4 more facts

chemical formula: C₅₅H₈₆N₂₀O₂₁S₂
canonical SMILES: CC1=C(N=C(N=C1N)C(CC(=O)N)NCC(C(=O)N)N)C(=O)NC(C(C2=CN=CN2)OC3C(C(C(C(O3)CO)O)O)OC4C(C(C(C(O4)CO)O)OC(=O)N)O)C(=O)NC(C)C(C(C)C(=O)NC(C(C)O)C(=O)NCCC5=NC(CS5)C6=NC(=CS6)C(=O)NCCCCN=C(N)N)O
isomeric SMILES: CC1=C(N=C(N=C1N)[C@H](CC(=O)N)NC[C@@H](C(=O)N)N)C(=O)N[C@@H]([C@H](C2=CN=CN2)O[C@H]3[C@H]([C@H]([C@@H]([C@@H](O3)CO)O)O)O[C@@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)OC(=O)N)O)C(=O)N[C@H](C)[C@H]([C@H](C)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCCC5=N[C@H](CS5)C6=NC(=CS6)C(=O)NCCCCN=C(N)N)O
subject has role: antimicrobial agent

Sources (2)

via Wikidata · CC0

~3 min read

Encyclopedic overview

5 sections

Contents

Properties
Usage
Plasmids with Zeocin Resistance
References
External links

{{Chembox | ImageFile = phleomycin D1.svg | ImageClass = skin-invert-image | ImageSize = 250px | SystematicName = (24R,7S,10S,11S,12R,15S,16R,182R,183S,184S,185S,186S,192R,193S,194S,195R,196R)-15-{6-Amino-2-[(1S)-3-amino-1-{[(2S)-2,3-diamino-3-oxopropyl]amino}-3-oxopropyl]-5-methylpyrimidine-4-carboxamido}-14-({4-[(diaminomethylidene)amino]butyl}carbamoyl)-11,184,185,203,205-pentahydroxy-7-[(1R)-1-hydroxyethyl]-186,206-bis(hydroxymethyl)-16-(1H-imidazol-5-yl)-10,12-dimethyl-6,9,14-trioxo-24,25-dihydro-17,19-dioxa-5,8,13-triaza-1(2),2(4,2)-bis([1,3]thiazola)-18(2,3),20(2)-bis(oxana)icosaphan-204-yl carbamate | OtherNames = | Section1 = | Section2 = | Section3 = }}

Excerpted from Wikipedia’s “phleomycin D1” article, available under the CC BY-SA 4.0 licence.