SCS-C007392

pyrrospirone I

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.5c01203 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

517.7 Da

Threshold ≤ 500

ALogP

4.24

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C32H39NO5

Molecular Weight:

517.6660 Da

SMILES:

CC1=C[C@]2(C)C(=O)C[C@]34C[C@](O)(Cc5ccc(cc5)O[C@H]5[C@@H]([C@@H]1[C@]1(C)C[C@H](C)C[C@H](C)[C@@H]51)[C@H]2C3=O)NC4=O

InChIKey:

                        DJXHULBSNKVOCR-DDIFOEQUSA-N
                        
                    

InChI:

InChI=1S/C32H39NO5/c1-16-10-17(2)24-26-22-23(30(24,5)11-16)18(3)12-29(4)21(34)14-31(27(35)25(22)29)15-32(37,33-28(31)36)13-19-6-8-20(38-26)9-7-19/h6-9,12,16-17,22-26,37H,10-11,13-15H2,1-5H3,(H,33,36)/t16-,17+,22+,23-,24+,25+,26+,29-,30+,31+,32-/m1/s1

Calculated Properties

ALogP:

4.244 lipophilicity

TPSA:

92.70 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

8 (1 aromatic)

Chiral Centers:

Fsp³:

0.6562 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007392

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 cancer cell lines A549 and HCT116	— Structured numeric value is not available in this record; see the primary reference.	10.1021/acs.jnatprod.5c01203 Journal of Natural Products

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