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SCS-C001519

Alternapyrone G

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

Structure of Alternapyrone G
Loading 3D structure...
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-F3 (NA)
Original source name: Arthrinium arundinis ZSDS1-F3; 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-F3; 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
456.6 Da
Threshold ≤ 500
ALogP
6.28
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C27H36O6
Molecular Weight:
456.5790 Da
SMILES:
CC(=C\C(CCCc1cc(C)c(C)o1)C(=O)O)/C=C(\C)C[C@@H](C)c1oc(=O)c(C)c(O)c1C
InChIKey:
XJAUYWSCEOOIHZ-GEMTZSLNSA-N
InChI:
InChI=1S/C27H36O6/c1-15(12-18(4)25-19(5)24(28)20(6)27(31)33-25)11-16(2)13-22(26(29)30)9-8-10-23-14-17(3)21(7)32-23/h11,13-14,18,22,28H,8-10,12H2,1-7H3,(H,29,30)/b15-11+,16-13+/t18-,22?/m1/s1
Calculated Properties
ALogP:
6.282 lipophilicity
TPSA:
100.88 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
5
Rotatable Bonds:
10
Ring Count:
2 (2 aromatic)
Chiral Centers:
2
Fsp³:
0.4815 fraction sp³ carbon

Database Information

Compound ID:
SCS-C001519
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 — LPS-stimulated BV2 microglia (M1 polarization, iNOS) 2.0 μM 10.1021/acs.jnatprod.4c00393 Journal of Natural Products
Neuroprotective / Neuromodulatory — Aβ?????-damaged cortical neurons 20.0 μM 10.1021/acs.jnatprod.4c00393 Journal of Natural Products
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Structure enlarged