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SCS-C001524

Alternapyrone E

Pathway: Polyketides Superclass: Linear polyketides Class: Open-chain polyketides
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Chemical Structure

Structure of Alternapyrone E
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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

Arthrinium arundinis ZSDS1-F8 (NA)
Original source name: Arthrinium arundinis ZSDS1-F8; Phakellia fusca Thiele
Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Amphisphaeriales Family Apiosporaceae Genus Apiospora Species Apiospora arundinis
Xisha Islands
DOI: 10.1021/acs.jnatprod.4c00393  · Journal of Natural Products
Phakellia fusca (NA)
Original source name: Arthrinium arundinis ZSDS1-F8; Phakellia fusca Thiele
Kingdom Metazoa Phylum Porifera Class Demospongiae Order Axinellida Family Axinellidae Genus Phakellia Species Phakellia fusca
Xisha Islands
DOI: 10.1021/acs.jnatprod.4c00393  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
488.6 Da
Threshold ≤ 500
ALogP
5.32
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C28H40O7
Molecular Weight:
488.6000 Da
SMILES:
CC(=CC(CCC[C@]1(CO)C=C(C)[C@H](C)O1)C(=O)O)C=C(C)CC(C)c1oc(=O)c(C)c(O)c1C
InChIKey:
KVOSGCOKGACRAO-NZDSKQBCSA-N
InChI:
InChI=1S/C28H40O7/c1-16(12-18(3)25-20(5)24(30)21(6)27(33)34-25)11-17(2)13-23(26(31)32)9-8-10-28(15-29)14-19(4)22(7)35-28/h11,13-14,18,22-23,29-30H,8-10,12,15H2,1-7H3,(H,31,32)/t18?,22-,23?,28+/m0/s1
Calculated Properties
ALogP:
5.316 lipophilicity
TPSA:
117.20 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
6
Rotatable Bonds:
11
Ring Count:
2 (1 aromatic)
Chiral Centers:
4
Fsp³:
0.5714 fraction sp³ carbon

Database Information

Compound ID:
SCS-C001524
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Linear polyketides
NPClassifier Class:
Open-chain polyketides
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
Anti-inflammatory inhibition_percent LPS-stimulated BV2 microglia (NO production) > 50.0 % 10.1021/acs.jnatprod.4c00393 Journal of Natural Products
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Structure enlarged