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14-epi-Berkeleylactone F

CAT: 0804-HY-N16392Size: 1 EachDry Ice: NoHazardous: No
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CAT#:0804-HY-N16392Size:1 Each
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Description
14-epi-Berkeleylactone F (Compound 8) is a C-14 epimer of Berkeleylactone F. 14-epi-Berkeleylactone F can be isolated from Penicillium turbatum NRRL 5630. 14-epi-Berkeleylactone F has no significant biological activity against bacterium (Staphylococcus aureus, Bacillus subtilis and E. coli), fungi Candida albicans, the parasite Giardia duodenalis and NS-1 murine myeloma cells[1].
CAS Number
3085255-21-3
UNSPSC
12352005
Target
Endogenous Metabolite
Related Pathways
Metabolic Enzyme/Protease
Field of Research
Infection
Smiles
O[C@H](CCCCCCCC[C@H](O)[C@H](O)/C=C/1)[C@@H](C)OC1=O
Molecular Formula
C16H28O5
Molecular Weight
300.39
References & Citations
[1]Cowled MS, et al. Stereodivergent Hydroxylation of Berkeleylactones by Penicillium turbatum. J Nat Prod. 2023 Mar 24;86 (3) :541-549.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

(3E,5R,6S,15R,16R)-5,6,15-trihydroxy-16-methyl-1-oxacyclohexadec-3-en-2-one
CAS Number3085255-21-3
PubChem CID178421285
IUPAC Name(3E,5R,6S,15R,16R)-5,6,15-trihydroxy-16-methyl-1-oxacyclohexadec-3-en-2-one
Molecular FormulaC16H28O5
Molecular Weight300.39
XLogP2.4
Topological Polar Surface Area87
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count0
Heavy Atom Count21
Formal Charge0
Complexity329
SMILES
C[C@@H]1[C@@H](CCCCCCCC[C@@H]([C@@H](/C=C/C(=O)O1)O)O)O
InChI
InChI=1S/C16H28O5/c1-12-13(17)8-6-4-2-3-5-7-9-14(18)15(19)10-11-16(20)21-12/h10-15,17-19H,2-9H2,1H3/b11-10+/t12-,13-,14+,15-/m1/s1
InChIKey
OXTXYWGSTRVDDS-JPPPHGFVSA-N
Chemical Structure
2D Structure
2D structure of (3E,5R,6S,15R,16R)-5,6,15-trihydroxy-16-methyl-1-oxacyclohexadec-3-en-2-one
CAS: 3085255-21-3
CID: 178421285
Formula: C16H28O5
MW: 300.39
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight300.39
XLogP32.4
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count0
Exact Mass300.19367399
Monoisotopic Mass300.19367399
Topological Polar Surface Area87 Ų
Heavy Atom Count21
Formal Charge0
Complexity329
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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