SCS-C008265

pyrrospirone O

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

Chemical Structure

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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

493.6 Da

Threshold ≤ 500

ALogP

4.37

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C30H39NO5

Molecular Weight:

493.6440 Da

SMILES:

C[C@@H]1C[C@H](C)[C@H]2[C@H]3Oc4ccc(cc4)C[C@@]4(O)C/C(=C(/O)[C@H]5[C@H](C)[C@H]6O[C@@]6(C)[C@H]([C@H]35)[C@]2(C)C1)C(=O)N4

InChIKey:

                        VZYOGXGVEZZUCQ-ZHUFHRRISA-N
                        
                    

InChI:

InChI=1S/C30H39NO5/c1-14-10-15(2)22-24-21-20(16(3)26-29(5,36-26)25(21)28(22,4)11-14)23(32)19-13-30(34,31-27(19)33)12-17-6-8-18(35-24)9-7-17/h6-9,14-16,20-22,24-26,32,34H,10-13H2,1-5H3,(H,31,33)/b23-19-/t14-,15+,16+,20+,21+,22+,24+,25-,26-,28-,29+,30-/m1/s1

Calculated Properties

ALogP:

4.369 lipophilicity

TPSA:

91.32 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (1 aromatic)

Chiral Centers:

Fsp³:

0.7000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008265

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
Antitumor	IC50	human lung adenocarcinoma H1975 cells	> 10.0 μM	10.1021/acs.jnatprod.2c00473 Journal of Natural Products
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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