Medermycin
Basic information
- CAS
60227-09-0- Standard SMILES
C[C@H]1O[C@@H]2CC(=O)O[C@@H]2C2=C1C(=O)c1c(ccc([C@H]3C[C@@H](N(C)C)[C@H](O)[C@@H](C)O3)c1O)C2=O- InChIKey
NYJGMJFBEVSQNN-CNRHASOASA-N- Molecular formula
- C24H27NO8
- Average molar mass
- 457.5 g/mol
- Monoisotopic mass
- 457.17366682
Overview
Medermycin is a member of p-quinones and a benzoisochromanequinone.
Names & identifiers
- Preferred name
- Medermycin
- IUPAC
- (11R,15R,17R)-5-[(2R,4R,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trione
- English name
- Medermycin
- Molecular formula
- C24H27NO8
- Molecular weight
- 457.47
Names & synonyms
Medermycin60227-09-0DTXSID601318319RefChem:156222DTXCID901748131LactoquinomycinCHEMBL2216825C12437(11R,15R,17R)-5-[(2R,4R,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-4-hydroxy-17-methyl-12,16-dioxatetracyclo[8.7.0.03,8.011,15]heptadeca-1(10),3(8),4,6-tetraene-2,9,13-trioneorb3024852SCHEMBL21093871CHEBI:31808
Show more names
[3aS,(-)]-3,3aβ,5,11bβ-Tetrahydro-7-hydroxy-5β-methyl-8-[3-(dimethylamino)-2,3,6-trideoxy-L-arabino-hexopyranosyl]-2H-furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione2H-Furo[3,2-b]naphtho[2,3-d]pyran-2,6,11-trione, 3,3a,5,11b-tetrahydro-7-hydroxy-5-methyl-8-[2,3,6-trideoxy-3-(dimethylamino)-β-D-arabino-hexopyranosyl]-, (3aR,5R,11bR)-
GLXC-24109BDBM50403054TN10069HY-117285Q27114688(2R)-2,3-bis(3,7,11,15-tetramethylhexadecoxy)propan-1-ol(1R)-1,5-Anhydro-2,3,6-trideoxy-3-(dimethylamino)-1-[(3aR,5R,11bR)-7-hydroxy-5-methyl-2,6,11-trioxo-3,3a,5,6,11,11b-hexahydro-2H-furo[3,2-b]naphtho[2,3-d]pyran-8-yl]-D-arabino-hexitol
Database identifiers
- CAS
60227-09-0- PubChem CID
- 12967404
- DTXSID
DTXSID601318319- ChEMBL
CHEMBL2216825- ChEBI
CHEBI:31808- Nikkaji
- J139.431B
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 123 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 2
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 899
Physicochemical properties
- EWG's Food Scores
- 1 · 1
Chemistry & industry
Applications
UsesLactoquinomycin A is a quinone antibiotic. Lactoquinomycin A has the activity of anti-Gram-positive bacteria and some Gram-negative bacteria, but the effect of anti-Gram-negative bacteria is weak and has no effect on fungi. Lactoquinomycin A inhibits a variety of cell lines including lymphoma L5178Y progenitor, Adriamycin resistant, Bleomycin-resistant, human leukemia K562, mouse leukemia L-1210 and mouse leukemia P 388 with ID50 (μg/mL) of 0.02, 0.006, 0.008, 0.033, 0.013 and 0.03, respectively[1].
Additional notes
DefinitionChEBI: Medermycin is a benzoisochromanequinone and a member of p-quinones.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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