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  3. 1-((E)-but-2-en-2-yl)-3,8-dihydroxy-6-((E)-4-hydroxybut-2-en-2-yl)-4,9-dimethyl-11H-dibenzo[b,e][1,4]dioxepin-11-one

SCS-C006724

1-((E)-but-2-en-2-yl)-3,8-dihydroxy-6-((E)-4-hydroxybut-2-en-2-yl)-4,9-dimethyl-11H-dibenzo[b,e][1,4]dioxepin-11-one

Pathway: Polyketides Superclass: Aromatic polyketides Class: Depsidones
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Chemical Structure

Structure of 1-((E)-but-2-en-2-yl)-3,8-dihydroxy-6-((E)-4-hydroxybut-2-en-2-yl)-4,9-dimethyl-11H-dibenzo[b,e][1,4]dioxepin-11-one
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Download: SDF SMILES

Source Information

Aspergillus sp. (coral-derived fungus)
Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species NA
South China Sea  · 1138 m
DOI: 10.3390/md24060214  · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight
396.4 Da
Threshold ≤ 500
ALogP
4.86
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C23H24O6
Molecular Weight:
396.4390 Da
SMILES:
C/C=C(\C)c1cc(O)c(C)c2c1C(=O)Oc1c(C)c(O)cc(/C(C)=C/CO)c1O2
InChIKey:
XEDLZAJMDZFDGK-GNXRPPCSSA-N
InChI:
InChI=1S/C23H24O6/c1-6-11(2)15-9-17(25)13(4)20-19(15)23(27)29-21-14(5)18(26)10-16(22(21)28-20)12(3)7-8-24/h6-7,9-10,24-26H,8H2,1-5H3/b11-6+,12-7+
Calculated Properties
ALogP:
4.858 lipophilicity
TPSA:
96.22 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
6
Rotatable Bonds:
3
Ring Count:
3 (2 aromatic)
Chiral Centers:
0
Fsp³:
0.2609 fraction sp³ carbon

Database Information

Compound ID:
SCS-C006724
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Aromatic polyketides
NPClassifier Class:
Depsidones
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

Biological Activity Data

Activity values are displayed only when a quantitative or clearly reported result is available. Tested organisms, cell lines and molecular targets are shown under Target / model.
Activity Assay Target / model Result Reference
Antitumor IC50 human cancer cell lines > 50.0 μM 10.3390/md24060214 Marine Drugs
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Structure enlarged