SCS-C007403
penicipyrroether A
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Tetramate alkaloids
Class: Pyrrocidine tetramate alkaloids
Glycoside
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
519.7 Da
Threshold ≤ 500
ALogP
4.36
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C32H41NO5
Molecular Weight:
519.6820 Da
SMILES:
CC1=C[C@]2(C)[C@H](C)O[C@@]3(O)C4=C[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]23)NC4=O
InChIKey:
NNMAETBPGAMTQR-CWVLRPJJSA-N
InChI:
InChI=1S/C32H41NO5/c1-16-11-17(2)25-26-23-24(30(25,6)12-16)18(3)13-29(5)19(4)38-32(36,27(23)29)22-15-31(35,33-28(22)34)14-20-7-9-21(37-26)10-8-20/h7-10,13,15-17,19,23-27,35-36H,11-12,14H2,1-6H3,(H,33,34)/t16-,17+,19+,23-,24-,25+,26+,27-,29-,30+,31-,32+/m1/s1
Calculated Properties
ALogP:
4.359 lipophilicity
TPSA:
88.02 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
5
Rotatable Bonds:
0
Ring Count:
8
(1 aromatic)
Chiral Centers:
12
Fsp³:
0.6562 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007403
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Tetramate alkaloids
NPClassifier Class:
Pyrrocidine tetramate alkaloids
Glycoside:
Yes
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 | — 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 |