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Polyketomycin

CAT: 0804-HY-106338-04Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-106338-04Size:5 mg
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Description
Polyketomycin is a tetracyclic quinone glycoside antibiotic isolated from Streptomyces sp. or Streptomyces diastatochromogenes. Polyketomycin inhibits growth of Gram-positive bacteria, and its MIC values is less than 0.2 μg/mL. Polyketomycin has antibacterial, anticancer, antimalarial activities[1][2][3].
CAS Number
200625-47-4
UNSPSC
12352005
Target
ADC Payload; Antibiotic; Bacterial; Parasite
Type
Natural Products
Related Pathways
Antibody-drug Conjugate/ADC Related; Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/polyketomycin.html
Solubility
10 mM in DMSO
Smiles
O[C@]1([C@@H]2O[C@]3([H])O[C@@H]([C@@H](O[C@@]4([H])C[C@@](O)([C@H](OC(C5=C(C(C)=CC=C5C)O)=O)[C@H](C)O4)C)CC3)C)[C@](C(C6=C(C(C)=C7C(C(C=C(OC)C7=O)=O)=C6O)C1)=O)(C(/C(C2=O)=C(O)\C)=O)O
Molecular Formula
C44H48O18
Molecular Weight
864.84
References & Citations
[1]Momose I, et al. Polyketomycin, a new antibiotic from Streptomyces sp. MK277-AF1. I. Taxonomy, production, isolation, physico-chemical properties and biological activities. J Antibiot (Tokyo) . 1998 Jan;51 (1) :21-5.|[2]Daum M, et al. Organisation of the biosynthetic gene cluster and tailoring enzymes in the biosynthesis of the tetracyclic quinone glycoside antibiotic polyketomycin. Chembiochem. 2009 Apr 17;10 (6) :1073-83.|[3]Otoguro K, In vitro antimalarial activities of the microbial metabolites. J Antibiot (Tokyo) . 2003 Mar;56 (3) :322-4.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
Plasmodium; Traditional Cytotoxic Agents

Chemical Information

6-((3-Acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,2,4a,5,7,10,12,12a-octahydrotetracen-1-yl)oxy)-2-methyloxan-3-yl 2,6-dideoxy-4-O-(2-hydroxy-3,6-dimethylbenzoyl)-3-C-methylhexopyranoside

Polyketomycin is a carbohydrate-containing antibiotic isolated from the culture broth of Streptomyces sp.MK277-AF1. It exhibits potent antibacterial activity against several Gram-positive bacterial strains and is also found to be cytotoxic against a number of tumour cell lines. It has a role as a metabolite, an antibacterial agent and an antineoplastic agent. It is a tertiary alpha-hydroxy ketone, a carbohydrate-containing antibiotic, a glycoside, a member of p-quinones, a member of pyrans, an enol, a member of phenols, a carbopolycyclic compound and a benzoate ester. It is functionally related to a 3,6-dimethylsalicylic acid.

CAS Number200625-47-4
PubChem CID5747698
IUPAC Name[(2S,3R,4R,6S)-6-[(2R,3S,6S)-6-[[(1S,4aS,12aR)-3-acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,12-dihydrotetracen-1-yl]oxy]-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 2-hydroxy-3,6-dimethylbenzoate
Molecular FormulaC44H48O18
Molecular Weight864.8
XLogP3.8
Topological Polar Surface Area279
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count18
Rotatable Bond Count9
Heavy Atom Count62
Formal Charge0
Complexity1940
SMILES
C[C@@H]1[C@H](CC[C@@H](O1)O[C@@H]2C(=O)C(=C([C@@]3([C@]2(CC4=C(C5=C(C(=O)C=C(C5=O)OC)C(=C4C3=O)O)C)O)O)O)C(=O)C)O[C@H]6C[C@@]([C@@H]([C@@H](O6)C)OC(=O)C7=C(C=CC(=C7O)C)C)(C)O
InChI
InChI=1S/C44H48O18/c1-16-9-10-17(2)33(47)28(16)41(53)62-39-21(6)59-27(15-42(39,7)54)60-24-11-12-26(58-20(24)5)61-40-36(50)30(19(4)45)37(51)44(56)38(52)31-22(14-43(40,44)55)18(3)29-32(35(31)49)23(46)13-25(57-8)34(29)48/h9-10,13,20-21,24,26-27,39-40,47,49,51,54-56H,11-12,14-15H2,1-8H3/t20-,21+,24+,26+,27+,39-,40-,42-,43-,44-/m1/s1
InChIKey
IFCBPTPGDINHLK-VSYKUZCLSA-N
Chemical Structure
2D Structure
2D structure of 6-((3-Acetyl-4,4a,6,12a-tetrahydroxy-9-methoxy-11-methyl-2,5,7,10-tetraoxo-1,2,4a,5,7,10,12,12a-octahydrotetracen-1-yl)oxy)-2-methyloxan-3-yl 2,6-dideoxy-4-O-(2-hydroxy-3,6-dimethylbenzoyl)-3-C-methylhexopyranoside
CAS: 200625-47-4
CID: 5747698
Formula: C44H48O18
MW: 864.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight864.8
XLogP33.8
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count18
Rotatable Bond Count9
Exact Mass864.28406468
Monoisotopic Mass864.28406468
Topological Polar Surface Area279 Ų
Heavy Atom Count62
Formal Charge0
Complexity1940
Isotope Atom Count0
Defined Atom Stereocenter Count10
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
bs-75666CPolyketomycin
207348Polyketomycin (Antibiotic K99-5147)

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