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SCS-C008264

pyrrospirone M

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

Structure of pyrrospirone M
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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
551.7 Da
Threshold ≤ 500
ALogP
2.86
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:
C32H41NO7
Molecular Weight:
551.6800 Da
SMILES:
CC(=O)[C@@H]1[C@@H]2[C@H](Oc3ccc(cc3)C[C@]3(O)C[C@]4(C[C@@H](O)[C@](C)(C=O)[C@@H]2C4=O)C(=O)N3)[C@@H]2[C@@H](C)C[C@@H](C)C[C@]21C
InChIKey:
AKUAGDSHKUBAIZ-ZUGABKLXSA-N
InChI:
InChI=1S/C32H41NO7/c1-16-10-17(2)23-26-22(24(18(3)35)29(23,4)11-16)25-27(37)31(13-21(36)30(25,5)15-34)14-32(39,33-28(31)38)12-19-6-8-20(40-26)9-7-19/h6-9,15-17,21-26,36,39H,10-14H2,1-5H3,(H,33,38)/t16-,17+,21-,22+,23+,24-,25+,26+,29-,30+,31+,32+/m1/s1
Calculated Properties
ALogP:
2.864 lipophilicity
TPSA:
130.00 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
7
Rotatable Bonds:
2
Ring Count:
7 (1 aromatic)
Chiral Centers:
12
Fsp³:
0.6875 fraction sp³ carbon

Database Information

Compound ID:
SCS-C008264
NPClassifier Pathway:
Alkaloids Amino acids and Peptides
NPClassifier Superclass:
Tetramate alkaloids
NPClassifier Class:
Pyrrocidine tetramate alkaloids
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
Enzyme inhibition IC50 CD45, TCPTP, SHP1, PTP1B, LAR > 200.0 μM 10.1021/acs.jnatprod.2c00473 Journal of Natural Products
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) >= 100.0 μg/mL 10.1021/acs.jnatprod.2c00473 Journal of Natural Products
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Structure enlarged