Phleomycin D1

CAT: 0804-HY-111428-02Size: 5 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-111428-02Size:5 mg

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Description

Phleomycin D1 (PLM D1), a glycopeptide antibiotic, is a member of the Bleomycin/Phleomycin family. Phleomycin D1 causes cell death by binding and cleaving DNA. Phleomycin D1 induces cell cycle arrest at S phase[1][2][3].

CAS Number

11031-11-1

Product Name Alternative

PLM D1

UNSPSC

12352005

Target

Antibiotic

Type

Reference compound

Related Pathways

Anti-infection

Applications

COVID-19-immunoregulation

Field of Research

Infection

Assay Protocol

https://www.medchemexpress.com/phleomycin-d1.html

Purity

99.40

Solubility

10 mM in DMSO

Smiles

O=C(C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C)N[C@H](C(N[C@H](C)[C@@H](O)[C@H](C)C(N[C@]([C@H](O)C)([H])C(NCCC2=N[C@@H](C3=NC(C(NCCCCNC(N)=N)=O)=CS3)CS2)=O)=O)=O)[C@H](C4=CN=CN4)O[C@H]5[C@H]([C@H]([C@@H]([C@@H](O5)CO)O)O)O[C@]6([H])[C@H]([C@H]([C@@H]([C@H](O6)CO)O)OC(N)=O)O

Molecular Formula

C55H86N20O21S2

Molecular Weight

1427.52

References & Citations

[1]Ishizuka M, et, al. Studies on antitumor activity, antimicrobial activity and toxicity of phleomycin. J Antibiot (Tokyo) . 1966 Nov;19 (6) :260-71.|[2]Huang CH, et, al. Bifunctional intercalation of antitumor antibiotics BBM-928A and echinomycin with deoxyribonucleic acid. Effects of intercalation on deoxyribonucleic acid degradative activity of bleomycin and phleomycin. Biochemistry. 1982 Jul 20;21 (15) :3704-10. |[3]Robles SJ, et al. Permanent cell cycle arrest in asynchronously proliferating normal human fibroblasts treated with doxorubicin or etoposide but not camptothecin. Biochem Pharmacol. 1999 Aug 15;58 (4) :675-85.

Shipping Conditions

Room Temperature

Storage Conditions

-20°C, 3 years; 4°C, 2 years (Powder)

Scientific Category

Reference compound1

Clinical Information

No Development Reported

Isoform

Glycopeptide

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 Number	11031-11-1
PubChem CID	71668282
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 Formula	C55H86N20O21S2
Molecular Weight	1427.5
XLogP	-10.3
Topological Polar Surface Area	744
Hydrogen Bond Donor Count	22
Hydrogen Bond Acceptor Count	32
Rotatable Bond Count	37
Heavy Atom Count	98
Formal Charge	0
Complexity	2750

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

CAS: 11031-11-1

CID: 71668282

Formula: C55H86N20O21S2

MW: 1427.5

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	1427.5
XLogP3	-10.3
Hydrogen Bond Donor Count	22
Hydrogen Bond Acceptor Count	32
Rotatable Bond Count	37
Exact Mass	1426.57178218
Monoisotopic Mass	1426.57178218
Topological Polar Surface Area	744 Å²
Heavy Atom Count	98
Formal Charge	0
Complexity	2750
Isotope Atom Count	0
Defined Atom Stereocenter Count	20
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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