SCS-C007404
GKK1032C
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
517.7 Da
Threshold ≤ 500
ALogP
4.22
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C32H39NO5
Molecular Weight:
517.6660 Da
SMILES:
C=C[C@@]1(C)C=C(C)[C@@H]2[C@@H]3[C@H](Oc4ccc(cc4)C[C@]4(O)NC(=O)[C@]5(O[C@H]54)C(=O)[C@H]31)[C@@H]1[C@@H](C)C[C@@H](C)C[C@]12C
InChIKey:
RBSWEDAZIYCYBW-JMSASLCWSA-N
InChI:
InChI=1S/C32H39NO5/c1-7-29(5)14-18(4)22-21-24(29)26(34)32-27(38-32)31(36,33-28(32)35)15-19-8-10-20(11-9-19)37-25(21)23-17(3)12-16(2)13-30(22,23)6/h7-11,14,16-17,21-25,27,36H,1,12-13,15H2,2-6H3,(H,33,35)/t16-,17+,21+,22-,23+,24+,25+,27+,29+,30+,31-,32+/m1/s1
Calculated Properties
ALogP:
4.218 lipophilicity
TPSA:
88.16 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
5
Rotatable Bonds:
1
Ring Count:
8
(1 aromatic)
Chiral Centers:
12
Fsp³:
0.6250 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007404
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 |