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Phleomycin D1

CAT: 1568-C13405-02Size: 25 mgDry Ice: NoHazardous: No
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CAT#:1568-C13405-02Size:25 mg
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CAS Number
11031-11-1
Synonyms
PLM D1
SKU
C13405-5mg
Target
Antibiotics
Applications
Microbiology
Molecular Formula
C55H86N20O21S2
Additionnal Information
Phleomycin D1 (PLM D1), a glycopeptide antibiotic, is a member of the Bleomycin/Phleomycin family. It causes cell death by binding and cleaving DNA. It shows antiproliferative activities and strong cytotoxicity against HT-29 cells.

Chemical Information

Zeocin

Phleomycin D1 is a glycopeptide originally isolated from the bacterium Streptomyces verticillus which contains a (4'R)-4',5'-dihydro-2,4'-bi-1,3-thiazole-2',4-diyl moiety with a a 4-guanidylbutylaminocarbonyl group attached to the 4-position of the terminal thiazole ring. Like all phleomycins, phleomycin D1 can form complexes with redox-active metals such as Co, Cu, and Fe. It has a role as an antimicrobial agent, an antibacterial agent, an antineoplastic agent, an antifungal agent and a bacterial metabolite. It is a chelate-forming peptide, a glycopeptide, a member of guanidines, a bi-1,3-thiazole and a disaccharide derivative.

CAS Number11031-11-1
PubChem CID71668282
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
Molecular FormulaC55H86N20O21S2
Molecular Weight1427.5
XLogP-10.3
Topological Polar Surface Area744
Hydrogen Bond Donor Count22
Hydrogen Bond Acceptor Count32
Rotatable Bond Count37
Heavy Atom Count98
Formal Charge0
Complexity2750
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
InChI
InChI=1S/C55H86N20O21S2/c1-19-32(72-45(75-43(19)58)24(11-30(57)79)67-12-23(56)44(59)85)49(89)74-34(40(25-13-63-18-68-25)94-53-42(38(83)36(81)28(14-76)93-53)95-52-39(84)41(96-55(62)91)37(82)29(15-77)92-52)50(90)69-21(3)35(80)20(2)46(86)73-33(22(4)78)48(88)65-10-7-31-70-27(17-97-31)51-71-26(16-98-51)47(87)64-8-5-6-9-66-54(60)61/h13,16,18,20-24,27-29,33-42,52-53,67,76-78,80-84H,5-12,14-15,17,56H2,1-4H3,(H2,57,79)(H2,59,85)(H2,62,91)(H,63,68)(H,64,87)(H,65,88)(H,69,90)(H,73,86)(H,74,89)(H2,58,72,75)(H4,60,61,66)/t20-,21+,22+,23-,24-,27+,28-,29+,33-,34-,35-,36+,37+,38-,39-,40-,41-,42-,52+,53-/m0/s1
InChIKey
CWCMIVBLVUHDHK-ZSNHEYEWSA-N
Chemical Structure
2D Structure
2D structure of Zeocin
CAS: 11031-11-1
CID: 71668282
Formula: C55H86N20O21S2
MW: 1427.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1427.5
XLogP3-10.3
Hydrogen Bond Donor Count22
Hydrogen Bond Acceptor Count32
Rotatable Bond Count37
Exact Mass1426.57178218
Monoisotopic Mass1426.57178218
Topological Polar Surface Area744 Ų
Heavy Atom Count98
Formal Charge0
Complexity2750
Isotope Atom Count0
Defined Atom Stereocenter Count20
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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