SCS-C007401
pyrrospirone Q
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Tetramate alkaloids
Class: Pyrrocidine tetramate alkaloids
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
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
501.7 Da
Threshold ≤ 500
ALogP
4.84
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C32H39NO4
Molecular Weight:
501.6670 Da
SMILES:
CC1=C[C@]2(C)C=C[C@]34C[C@](O)(Cc5ccc(cc5)O[C@@H]5[C@@H]6[C@@H](C)C[C@@H](C)C[C@@]6(C)[C@@H]5[C@H]1[C@H]2C3=O)NC4=O
InChIKey:
KKLSFCFFZMWRNC-IYWAHYBMSA-N
InChI:
InChI=1S/C32H39NO4/c1-17-12-18(2)23-26-24(30(23,5)13-17)22-19(3)14-29(4)10-11-31(27(34)25(22)29)16-32(36,33-28(31)35)15-20-6-8-21(37-26)9-7-20/h6-11,14,17-18,22-26,36H,12-13,15-16H2,1-5H3,(H,33,35)/t17-,18+,22+,23+,24-,25+,26-,29+,30-,31+,32-/m1/s1
Calculated Properties
ALogP:
4.841 lipophilicity
TPSA:
75.63 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
4
Rotatable Bonds:
0
Ring Count:
8
(1 aromatic)
Chiral Centers:
11
Fsp³:
0.6250 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007401
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
Natural product databases
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 |
| Antibacterial | MIC | six pathogenic bacteria | — Structured numeric value is not available in this record; see the primary reference. | 10.1021/acs.jnatprod.5c01203 Journal of Natural Products |