3,6-Methanocylopenta(c)pyran-1(3H)-one, hexahydro-7-benzoyl-5-(4-methoxy-2-oxo-2H-pyran-6-yl)-4a,6,7a,8-tetrahydroxy-, (3R-(3-alpha,4a-beta,5-alpha,6-beta,7-beta,7a-beta,8R*))-
Basic information
- CAS
59678-46-5- Standard SMILES
COc1cc([C@H]2[C@@]3(O)C(O)[C@H]4C[C@]2(O)[C@](O)(C(=O)O4)[C@H]3C(=O)c2ccccc2)oc(=O)c1- InChIKey
CTBBEXWJRAPJIZ-VKMWXFLYSA-N- Molecular formula
- C22H20O10
- Average molar mass
- 444.4 g/mol
- Monoisotopic mass
- 444.10564683
Overview
See also: Vulgamycin (annotation moved to); Enterocin (annotation moved to).
Names & identifiers
- Preferred name
- 3,6-Methanocylopenta(c)pyran-1(3H)-one, hexahydro-7-benzoyl-5-(4-methoxy-2-oxo-2H-pyran-6-yl)-4a,6,7a,8-tetrahydroxy-, (3R-(3-alpha,4a-beta,5-alpha,6-beta,7-beta,7a-beta,8R*))-
- IUPAC
- (1S,2S,3S,6R,8R,9S)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.03,8]decan-4-one
- English name
- ENTEROCIN
- Molecular formula
- C22H20O10
- Molecular weight
- 444.39
Names & synonyms
2M8WGY5QPQC22H20O10MFCD01714909UNII-2M8WGY5QPQSCHEMBL293842233,6-Methanocylopenta(c)pyran-1(3H)-one, hexahydro-7-benzoyl-5-(4-methoxy-2-oxo-2H-pyran-6-yl)-4a,6,7a,8-tetrahydroxy-, (3R-(3-alpha,4a-beta,5-alpha,6-beta,7-beta,7a-beta,8R*))-Q15427931(1S,2S,3S,6R,8R,9S)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxo-pyran-2-yl)-5-oxatricyclo[4.3.1.03,8]decan-4-one(3R,4aR,5S,6S,7S,7aS)-7-Benzoyl-4a,6,7a,8-tetrahydroxy-5-(4-methoxy-2-oxo-2H-pyran-6-yl)hexahydro-3,6-methanocyclopenta[c]pyran-1(3H)-oneENTEROCINVulgamycinAids035399
Show more names
Aids-035399Enterocin, vulgamycinVulgaMycin, A 5294, WS 80963,6-Methanocyclopenta(C)pyran-1(3H)-one, 7-benzoylhexahydro-4A,6,7A,8-tetrahydroxy-5-(4-methoxy-2-oxo-2H-pyran-6-yl)-, (3R,4ar,5S,6S,7S,7as,8R)-(3R,8R)-7α-Benzoyl-4,4a,5,6,7,7a-hexahydro-4aα,6α,7aα,8-tetrahydroxy-5β-(4-methoxy-2-oxo-2H-pyran-6-yl)-3β,6-methanocyclopenta[c]pyran-1(3H)-one
Properties
Computed structural properties
- XLogP
- -0.9
- Topological polar surface area
- 160 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 4
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 948
Physicochemical properties
- Boiling point
- 726.3 · 726.3±60.0 °C(Predicted)
- Density
- 1.67 · 1.67±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in DMSO
- form
- solid
- pka
- 10.86 · 10.86±0.70(Predicted)
- color
- White
- FDA UNII
- 2 M8WGY5QPQ · 2M8WGY5QPQ
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 21 · NA.21
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312+H332-H315-H319-H335
- Precautionary statements
- 280 · P280
- WGK Germany
- 3 · WGK 3
- HS Code
- 29419000 · 29419000
- Storage Class
- 11 · 11 - Combustible Solids
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
- WGK 3
- hs_code
- 29419000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332-H315-H319-H335
- Precautionary statements
- P280
Chemistry & industry
Applications
UsesEnterocin is a potent antibiotic with broad spectrum activity against Gram +ve and Gram -ve bacteria.
UsesEnterocin is a potent antibiotic with broad spectrum activity against Gram positive and Gram negative bacteria. Although the mechanism of action of enterocin is unknown, it acts synergistically with streptomycin and chloramphenicol. The genetics of enterocin biosynthesis have been extensively investigated. Enterocin is a small molecular weight secondary metabolite and should not be confused with bacterial proteins isolated from Enterococci, generically referred to as "enterocins".
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