1. Home
  2. Compounds
  3. pyrrospirone U

SCS-C007394

pyrrospirone U

Pathway: Alkaloids | Amino acids and Peptides Superclass: Tetramate alkaloids Class: Pyrrocidine tetramate alkaloids
Back to List

Chemical Structure

Structure of pyrrospirone U
Loading 3D structure...
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
549.7 Da
Threshold ≤ 500
ALogP
4.42
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:
C33H43NO6
Molecular Weight:
549.7080 Da
SMILES:
CO[C@H]1C[C@]23C[C@](O)(Cc4ccc(cc4)O[C@H]4[C@H]5[C@@H](C(C)=C[C@](C)(O1)[C@@H]5C2=O)[C@]1(C)C[C@H](C)C[C@H](C)[C@@H]41)NC3=O
InChIKey:
VSUDGIJQSQRFAE-ONJMXZKTSA-N
InChI:
InChI=1S/C33H43NO6/c1-17-11-18(2)25-27-23-24(30(25,4)12-17)19(3)13-31(5)26(23)28(35)32(15-22(38-6)40-31)16-33(37,34-29(32)36)14-20-7-9-21(39-27)10-8-20/h7-10,13,17-18,22-27,37H,11-12,14-16H2,1-6H3,(H,34,36)/t17-,18+,22-,23+,24-,25+,26+,27+,30+,31+,32+,33-/m1/s1
Calculated Properties
ALogP:
4.416 lipophilicity
TPSA:
94.09 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
6
Rotatable Bonds:
1
Ring Count:
8 (1 aromatic)
Chiral Centers:
12
Fsp³:
0.6970 fraction sp³ carbon

Database Information

Compound ID:
SCS-C007394
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
Back to Compounds
Structure enlarged