Chrysomycin A Streptomyces sp
Basic information
- CAS
82196-88-1- Standard SMILES
C=Cc1cc(OC)c2c(c1)c(=O)oc1c2cc(OC)c2c(O)ccc([C@@H]3O[C@H](C)[C@H](O)[C@@](C)(O)[C@H]3O)c21- InChIKey
OMDANBMKOUVKAG-WZNMFJNZSA-N- Molecular formula
- C28H28O9
- Average molar mass
- 508.5 g/mol
- Monoisotopic mass
- 508.17333247
Overview
Chrysomycin a is a glycoside.
Names & identifiers
- Preferred name
- Chrysomycin A Streptomyces sp
- IUPAC
- 8-ethenyl-1-hydroxy-10,12-dimethoxy-4-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-4,6-dimethyloxan-2-yl]naphtho[1,2-c]isochromen-6-one
- English name
- Chrysomycin A
- Molecular formula
- C28H28O9
- Molecular weight
- 508.52
Names & synonyms
CHEMBL4072918C28H28O9NSC 613946Chrysomycin A Streptomyces spSCHEMBL29470696CHEBI:191084GLXC-26225BDBM50235918HB3835MFCD07370133Chrysomycin A, >=98% (HPLC), solidDA-51882
Show more names
A,ChrysoMycinVirenomycin VChrysomycin VCHRYSOMYCIN A(+)-Virenomycin VCHRYSOMYCIN A USP/EP/BPChrysomycin A, DNA synthesis inhibitorChrysoMycin V, VirenoMycin V, Albacarcin V8-ethenyl-1-hydroxy-10,12-dimethoxy-4-(3,4,5-trihydroxy-4,6-dimethyloxan-2-yl)naphtho[1,2-c]isochromen-6-one
HY-126771CS-0107231H501661-Hydroxy-10,12-dimethoxy-4-((2S,3S,4R,5S,6R)-3,4,5-trihydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)-8-vinyl-6H-dibenzo[c,h]chromen-6-one1-hydroxy-10,12-dimethoxy-4-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-4,6-dimethyl-tetrahydropyran-2-yl]-8-vinyl-naphtho[1,2-c]isochromen-6-one
Database identifiers
- CAS
82196-88-1- PubChem CID
- 73468
- ChEMBL
CHEMBL4072918- ChEBI
CHEBI:191084- Nikkaji
- J168.852I
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 135 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 4
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 867
Physicochemical properties
- Melting point
- 234 · 234-236 °C
- Boiling point
- 799.7 · 799.7±60.0 °C(Predicted)
- Density
- 1.405 · 1.405±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- DMF: soluble
- pka
- 8.55 · 8.55±0.20(Predicted)
- form
- solid
- color
- Yellow to greenish
- InChIKey
- OMDANBMKOUVKAG-BMGMCLONNA-N
- SMILES
- C12OC(=O)C3=C(C(OC)=CC(C=C)=C3)C=1C=C(OC)C1C(O)=CC=C(C2=1)[C@@H]1O[C@H](C)[C@H](O)[C@@](C)(O)[C@H]1O |&1:26,28,30,32,35,r|
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312-H319-H351
- Precautionary statements
- 201 · P201-P202-P264-P270-P280-P301+P312-P330-P302+P352-P305+P351+P338-P308+P313-P321-P362+P364-P337+P313-P405-P501
- WGK Germany
- 3 · 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- Hazard statements
- H302+H312-H319-H351
- Precautionary statements
- P201-P202-P264-P270-P280-P301+P312-P330-P302+P352-P305+P351+P338-P308+P313-P321-P362+P364-P337+P313-P405-P501
Chemistry & industry
Applications
HistoryChrysomycin A was first isolated from the Streptomyces A-419 strain in 1955 as a mixture of chloramphenicol A and B, and is considered one of the most promising candidates for the treatment of infections caused by multidrug-resistant Gram-positive bacteria. Strain 891, isolated from sediments in the South China Sea, has been found to yield the highest concentration of Chrysomycin A (3,600 mg/L) of all known strains under optimal conditions.
UsesChrysomycin A is the major analogue in a complex of C-glycoside antitumor actives isolated from Streptomyces. Chrysomycin A, with a vinyl group in the 8-position, is the most potent analogue of the complex, and is thought to act as an inhibitor of the catalytic activity of human topoisomerase II. Chrysomycin A has a potent antibacterial, antifungal, antiviral and antitumor profile. More recent research on related metabolites, the gilvocarcins, suggests that chrysomycins may act as photoactivated cross-linkers of DNA to histones.
UsesChrysomycin A is a potent antibacterial, antifungal and antiviral compound.
Additional notes
DefinitionChEBI: Chrysomycin a is a glycoside.
Related reactions
0 records
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Compound notes
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