SCS-C008266

pyrrospirone L

Pathway: Alkaloids | Amino acids and Peptides Superclass: Tetramate alkaloids Class: Pyrrocidine tetramate alkaloids

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

Penicillium sp. (soft coral-derived fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species NA

South China Sea

DOI: 10.1021/acs.jnatprod.2c00473 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

581.7 Da

Threshold ≤ 500

ALogP

3.56

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C33H43NO8

Molecular Weight:

581.7060 Da

SMILES:

CO[C@@]12Cc3ccc(cc3)O[C@H]3[C@@H]4[C@H]5C(=O)[C@](C[C@H](O)OO[C@@]5(C)[C@H]5O[C@@]5(C)[C@H]4[C@]4(C)C[C@H](C)C[C@H](C)[C@@H]34)(C1)C(=O)N2

InChIKey:

                        XLNGKUVJTRUXGF-GGGHLTRXSA-N
                        
                    

InChI:

InChI=1S/C33H43NO8/c1-16-11-17(2)22-24-21-23-26(36)32(15-33(38-6,34-28(32)37)13-18-7-9-19(39-24)10-8-18)14-20(35)41-42-30(23,4)27-31(5,40-27)25(21)29(22,3)12-16/h7-10,16-17,20-25,27,35H,11-15H2,1-6H3,(H,34,37)/t16-,17+,20-,21+,22+,23+,24+,25-,27-,29-,30-,31+,32+,33+/m1/s1

Calculated Properties

ALogP:

3.559 lipophilicity

TPSA:

115.85 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

9 (1 aromatic)

Chiral Centers:

Fsp³:

0.7576 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008266

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Tetramate alkaloids

NPClassifier Class:

Pyrrocidine tetramate alkaloids

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
Antibacterial	IC50	six tested pathogens (Bacillus amyloliquefaciens, B. subtilis, Escherichia coli, Staphylococcus aureus, S. aureus MRSA, Streptococcus agalactiae)	20.0–50.0 μg/mL	10.1021/acs.jnatprod.2c00473 Journal of Natural Products

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