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ε-Rhodomycinone

CAT: 0804-HY-168779-02Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-168779-02Size:1 mg
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Description
ε-Rhodomycinone is a bacterial metabolite found in S. griseoruber. It is a precursor to Rhodomycin D, which is an intermediate in the bioconversion of ε-rhodomycinone to Daunorubicin and Doxorubicin (HY-15142R)[2][3].
CAS Number
21288-60-8
UNSPSC
12352005
Target
Bacterial; Drug Intermediate
Related Pathways
Anti-infection; Others
Field of Research
Cancer; Infection; Neurological Disease
Smiles
COC([C@@H]1C2=C([C@H](C[C@]1(O)CC)O)C(O)=C3C(C(C4=CC=CC(O)=C4C3=O)=O)=C2O)=O
Molecular Formula
C22H20O9
Molecular Weight
428.39
References & Citations
[1]Podojil M, et al. Production of rhodomycins in Streptomyces griseoruber 4620. Folia Microbiol (Praha) . 1980;25 (6) :464-6.|[2]Olano C, et al. A two-plasmid system for the glycosylation of polyketide antibiotics: bioconversion of epsilon-rhodomycinone to rhodomycin D. Chem Biol. 1999 Dec;6 (12) :845-55.|[3]Dickens ML, et al. In vivo and in vitro bioconversion of epsilon-rhodomycinone glycoside to doxorubicin: functions of DauP, DauK, and DoxA. J Bacteriol. 1997 Apr;179 (8) :2641-50.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Methyl (1R,2R,4S)-2-ethyl-1,2,3,4,6,11-hexahydro-2,4,5,7,12-pentahydroxy-6,11-dioxo-1-naphthacenecarboxylate

Epsilon-rhodomycinone is a carboxylic ester that is the methyl ester of (1R,2R,4S)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid. It is a methyl ester, a polyphenol, a carbopolycyclic compound, a tetracenomycin and a member of tetracenequinones.

CAS Number21288-60-8
PubChem CID99207
IUPAC Namemethyl (1R,2R,4S)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate
Molecular FormulaC22H20O9
Molecular Weight428.4
XLogP2.7
Topological Polar Surface Area162
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Heavy Atom Count31
Formal Charge0
Complexity768
SMILES
CC[C@]1(C[C@@H](C2=C([C@H]1C(=O)OC)C(=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)O)O)O
InChI
InChI=1S/C22H20O9/c1-3-22(30)7-10(24)12-13(16(22)21(29)31-2)20(28)14-15(19(12)27)18(26)11-8(17(14)25)5-4-6-9(11)23/h4-6,10,16,23-24,27-28,30H,3,7H2,1-2H3/t10-,16-,22+/m0/s1
InChIKey
PYFOXRACBORDCT-GOSXWKPOSA-N
Chemical Structure
2D Structure
2D structure of Methyl (1R,2R,4S)-2-ethyl-1,2,3,4,6,11-hexahydro-2,4,5,7,12-pentahydroxy-6,11-dioxo-1-naphthacenecarboxylate
CAS: 21288-60-8
CID: 99207
Formula: C22H20O9
MW: 428.4
Interactive 3D Structure
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View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight428.4
XLogP32.7
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Exact Mass428.11073221
Monoisotopic Mass428.11073221
Topological Polar Surface Area162 Ų
Heavy Atom Count31
Formal Charge0
Complexity768
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
WAA28860-01ε-Rhodomycinone

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