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SCS-C007386

pyrrospirone R

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

Structure of pyrrospirone R
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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.5c01203  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
532.7 Da
Threshold ≤ 500
ALogP
4.67
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:
C32H40N2O5
Molecular Weight:
532.6810 Da
SMILES:
C=C1C=C(C)[C@@H]2[C@H]3[C@H]1C(=O)[C@]1(C/C=N/O)C[C@](O)(Cc4ccc(cc4)O[C@@H]3[C@@H]3[C@@H](C)C[C@@H](C)C[C@]32C)NC1=O
InChIKey:
XDTLCZOGAZWNSL-YQAHAQCNSA-N
InChI:
InChI=1S/C32H40N2O5/c1-17-12-19(3)26-27-24-23(18(2)13-20(4)25(24)30(26,5)14-17)28(35)31(10-11-33-38)16-32(37,34-29(31)36)15-21-6-8-22(39-27)9-7-21/h6-9,11,13,17,19,23-27,37-38H,2,10,12,14-16H2,1,3-5H3,(H,34,36)/b33-11+/t17-,19+,23+,24-,25-,26+,27+,30+,31+,32-/m1/s1
Calculated Properties
ALogP:
4.671 lipophilicity
TPSA:
108.22 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
6
Rotatable Bonds:
2
Ring Count:
7 (1 aromatic)
Chiral Centers:
10
Fsp³:
0.5938 fraction sp³ carbon

Database Information

Compound ID:
SCS-C007386
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
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
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Structure enlarged