SCS-C000584
aerothionin
Pathway: Alkaloids
Superclass: Ornithine alkaloids
Class: Polyamines
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
Fascaplysinopsis reticulata
(NA)
Kingdom
Metazoa
Phylum
Porifera
Class
Demospongiae
Order
Dictyoceratida
Family
Thorectidae
Genus
Fascaplysinopsis
Species
Fascaplysinopsis reticulata
Xisha Islands
DOI:
10.1038/s41598-019-38696-3
· Scientific Reports
Himerometra magnipinna
(NA)
Kingdom
Metazoa
Phylum
Echinodermata
Class
Crinoidea
Order
Comatulida
Family
Himerometridae
Genus
Himerometra
Species
Himerometra magnipinna
South China Sea
· 8 m
DOI:
10.1021/np060601p
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
818.1 Da
Threshold ≤ 500
ALogP
2.84
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
10
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C24H26Br4N4O8
Molecular Weight:
818.1000 Da
SMILES:
COC1=C(Br)[C@H](O)[C@@]2(C=C1Br)CC(C(=O)NCCCCNC(=O)C1=NO[C@]3(C=C(Br)C(OC)=C(Br)[C@@H]3O)C1)=NO2
InChIKey:
BJWQSQOWGBUSFC-UWXQAFAOSA-N
InChI:
InChI=1S/C24H26Br4N4O8/c1-37-17-11(25)7-23(19(33)15(17)27)9-13(31-39-23)21(35)29-5-3-4-6-30-22(36)14-10-24(40-32-14)8-12(26)18(38-2)16(28)20(24)34/h7-8,19-20,33-34H,3-6,9-10H2,1-2H3,(H,29,35)(H,30,36)/t19-,20-,23+,24+/m0/s1
Calculated Properties
ALogP:
2.842 lipophilicity
TPSA:
160.30 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
10
Rotatable Bonds:
9
Ring Count:
4
(0 aromatic)
Chiral Centers:
4
Fsp³:
0.5000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000584
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Ornithine alkaloids
NPClassifier Class:
Polyamines
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 |
|---|---|---|---|---|
| Enzyme inhibition | — | tyrosine phosphatase 1B | 7.67 μM | 10.1038/s41598-019-38696-3 Scientific Reports |
| Antibacterial | inhibition zone | Streptomyces 85E HFI assay | Compounds 1 and 3 exhibited inhibitory activity to Streptomyces 85E as a “bald” zone (11 mm) at the concentration of 80 μg/disk, whereas compound 2 was inactive. | 10.1021/np060601p Journal of Natural Products |