SCS-C000611

spirostaphylotrichin A

Pathway: Amino acids and Peptides | Polyketides Superclass: Cyclic polyketides Class: 3-Spirotetramic acids

Chemical Structure

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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

Cochliobolus lunatus SCSIO 41401 (gorgonian-derived fungus)

Original source name: Cochliobolus lunatus SCSIO41401

Kingdom Fungi Phylum Ascomycota Class Dothideomycetes Order Pleosporales Family Pleosporaceae Genus Curvularia Species Cochliobolus lunatus

South China Sea

DOI: 10.1021/acs.jnatprod.8b00656 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

279.3 Da

Threshold ≤ 500

ALogP

0.09

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C14H17NO5

Molecular Weight:

279.2900 Da

SMILES:

C=C1[C@H](O)[C@@]2(C(=O)N1OC)/C(=C/CC)C=CC(=O)C2O

InChIKey:

                        UEEZHRJFRYRGNC-KUIZCYACSA-N
                        
                    

InChI:

InChI=1S/C14H17NO5/c1-4-5-9-6-7-10(16)12(18)14(9)11(17)8(2)15(20-3)13(14)19/h5-7,11-12,17-18H,2,4H2,1,3H3/b9-5+/t11-,12?,14-/m0/s1

Calculated Properties

ALogP:

0.087 lipophilicity

TPSA:

87.07 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (0 aromatic)

Chiral Centers:

Fsp³:

0.4286 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000611

NPClassifier Pathway:

Amino acids and Peptides Polyketides

NPClassifier Superclass:

Cyclic polyketides

NPClassifier Class:

3-Spirotetramic acids

Glycoside:

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
Antiviral	—	influenza A virus	— Structured numeric value is not available in this record; see the primary reference.	10.1021/acs.jnatprod.8b00656 Journal of Natural Products

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