SCS-C008267

pyrrospirone N

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

565.7 Da

Threshold ≤ 500

ALogP

3.52

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C33H43NO7

Molecular Weight:

565.7070 Da

SMILES:

CO[C@@]12Cc3ccc(cc3)O[C@H]3[C@H]([C@H]4C(=O)[C@](C[C@@H](O)[C@]4(C)C=O)(C1)C(=O)N2)[C@@H](C(C)=O)[C@]1(C)C[C@H](C)C[C@H](C)[C@@H]31

InChIKey:

                        KHVIXDAVPLFLHA-YUVYPMEWSA-N
                        
                    

InChI:

InChI=1S/C33H43NO7/c1-17-11-18(2)24-27-23(25(19(3)36)30(24,4)12-17)26-28(38)32(14-22(37)31(26,5)16-35)15-33(40-6,34-29(32)39)13-20-7-9-21(41-27)10-8-20/h7-10,16-18,22-27,37H,11-15H2,1-6H3,(H,34,39)/t17-,18+,22-,23+,24+,25-,26+,27+,30-,31+,32+,33+/m1/s1

Calculated Properties

ALogP:

3.518 lipophilicity

TPSA:

119.00 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (1 aromatic)

Chiral Centers:

Fsp³:

0.6970 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008267

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
Other specified activity	IC50	several PTPs	39.4–100.0 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)	>= 100.0 μg/mL	10.1021/acs.jnatprod.2c00473 Journal of Natural Products

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