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SCS-C001520

Alternapyrone H

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

Structure of Alternapyrone H
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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-F4 (NA)
Original source name: Arthrinium arundinis ZSDS1-F4; 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-F4; 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
474.6 Da
Threshold ≤ 500
ALogP
6.18
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C28H42O6
Molecular Weight:
474.6380 Da
SMILES:
CCC(C)/C=C(\CO)CCCC(/C=C(C)/C=C(\C)C[C@@H](C)c1oc(=O)c(C)c(O)c1C)C(=O)O
InChIKey:
PYRMVXWEDUHREB-MDPNWLRQSA-N
InChI:
InChI=1S/C28H42O6/c1-8-17(2)14-23(16-29)10-9-11-24(27(31)32)15-19(4)12-18(3)13-20(5)26-21(6)25(30)22(7)28(33)34-26/h12,14-15,17,20,24,29-30H,8-11,13,16H2,1-7H3,(H,31,32)/b18-12+,19-15+,23-14-/t17?,20-,24?/m1/s1
Calculated Properties
ALogP:
6.184 lipophilicity
TPSA:
107.97 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
5
Rotatable Bonds:
13
Ring Count:
1 (1 aromatic)
Chiral Centers:
3
Fsp³:
0.5714 fraction sp³ carbon

Database Information

Compound ID:
SCS-C001520
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