Basic information
- CAS
61116-33-4- Standard SMILES
O=C(/C=C/C=C/C=C/C1CCCCC1)NC1=C[C@@](O)(/C=C/C=C/C=C/C(=O)NC2=C(O)CCC2=O)[C@@H]2O[C@@H]2C1=O- InChIKey
SSHVAUUEPNULMP-JHWDTTIQSA-N- Molecular formula
- C31H34N2O7
- Average molar mass
- 546.6 g/mol
- Monoisotopic mass
- 546.23660143
Overview
Asukamycin is a polyketide that is a member of the manumycin family of antibiotics and exhibits strong antibacterial, antifungal, and antineoplastic activities. Isolated from from the actinomycete bacterium Streptomyces nodosus subsp. asukaensis. It has a role as an antimicrobial agent, an antibacterial agent, an antineoplastic agent, an antifungal agent and a bacterial metabolite. It is a secondary carboxamide, a polyketide, a tertiary alcohol, an organic heterobicyclic compound, an epoxide and an enamide. It is functionally related to a 4-hydroxyprotoasukamycin.
Names & identifiers
- Preferred name
- Asukamycin
- IUPAC
- (2E,4E,6E)-7-cyclohexyl-N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]hepta-2,4,6-trienamide
- English name
- asukamycin
- Molecular formula
- C31H34N2O7
- Molecular weight
- 546.61
Names & synonyms
Asukamycin61116-33-4asukamycin A1CHEBI:73481DTXSID401318456(2E,4E,6E)-7-cyclohexyl-N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopenten-1-yl)amino]-7-oxohepta-1,3,5-trienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]hepta-2,4,6-trienamide(2E,4E,6E)-7-cyclohexyl-N-[(1S,5S,6R)-5-hydroxy-5-{(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)amino]-7-oxohepta-1,3,5-trien-1-yl}-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]hepta-2,4,6-trienamide(2E,4E,6E)-7-cyclohexyl-N-((1S,5S,6R)-5-hydroxy-5-((1E,3E,5E)-7-((2-hydroxy-5-oxocyclopent-1-en-1-yl)amino)-7-oxohepta-1,3,5-trien-1-yl)-2-oxo-7-oxabicyclo(4.1.0)hept-3-en-3-yl)hepta-2,4,6-trienamide(2E,4E,6E)-7-cyclohexyl-N-((1S,5S,6R)-5-hydroxy-5-((1E,3E,5E)-7-((2-hydroxy-5-oxocyclopenten-1-yl)amino)-7-oxohepta-1,3,5-trienyl)-2-oxo-7-oxabicyclo(4.1.0)hept-3-en-3-yl)hepta-2,4,6-trienamideRefChem:115374DTXCID701748266AM 1042
Show more names
AM-1042aviamycin7-Cyclohexyl-N-[5-hydroxy-5-[7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxo-1,3,5-heptatrienyl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-heptatrienamide
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 145 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 10
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 1,270
Experimental & physicochemical properties
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl amines [FA0802]
Physicochemical properties
- Boiling point
- 910 · 910.0±65.0 °C(Predicted)
- Density
- 1.32 · 1.32±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
- form
- A solid
- pka
- 3.8 · 3.80±0.30(Predicted)
- color
- Light yellow to yellow
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501
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
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Applications
UsesAsukamycin is an unusual trienoic acid amide metabolite produced by Streptomyces nodosus, reported by Omura and colleagues at the Kitasato Institute, Japan, in 1976. Asukamycin belongs to the manumycin class that comprises two trienoic acid amides pivoted on a central cyclohexenone ring to give the molecule an unprecedented angular geometry. Asukamycin is active against Gram positive bacteria, tumor cell lines and protozoans, notably coccidia. Asukamycin’s cell toxicity is accompanied by activation of Caspases 3 and 8.
Suppliers17 total
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd+86-13119157289 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
孟成科技（上海）有限公司400-820-6829 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
上海一研生物科技有限公司021-69985186 13611928337 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
Alfa Chemistry+1-5166625404 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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