SCS-C007922
dassonmycin A
Pathway: 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
Nocardiopsis dassonvillei SCSIO 40065
(NA)
Original source name: Nocardiopsis dassonvillei SCSIO 40065 (associated with marine sponge Petrosia sp.)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Streptosporangiales
Family
Nocardiopsidaceae
Genus
Nocardiopsis
Species
Nocardiopsis dassonvillei
South China Sea
· 20 m
DOI:
10.1021/acs.orglett.1c00328
· Organic Letters
Drug-likeness (Lipinski Ro5)
Molecular Weight
344.4 Da
Threshold ≤ 500
ALogP
0.53
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C17H16N2O4S
Molecular Weight:
344.3920 Da
SMILES:
CN1C(=O)[C@H]2CSC3=C(C(=O)c4ccccc4C3=O)N2C[C@@H]1CO
InChIKey:
UDOVXKDLSJAHMV-BXKDBHETSA-N
InChI:
InChI=1S/C17H16N2O4S/c1-18-9(7-20)6-19-12(17(18)23)8-24-16-13(19)14(21)10-4-2-3-5-11(10)15(16)22/h2-5,9,12,20H,6-8H2,1H3/t9-,12-/m1/s1
Calculated Properties
ALogP:
0.527 lipophilicity
TPSA:
77.92 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
6
Rotatable Bonds:
1
Ring Count:
4
(1 aromatic)
Chiral Centers:
2
Fsp³:
0.3529 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007922
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
N/A
NPClassifier Class:
N/A
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 |
|---|---|---|---|---|
| Antibacterial | MIC | Bacillus subtilis 1064, Micrococcus luteus SCSIO ML01, Staphylococcus aureus ATCC 29213, methicillin-resistant Staphylococcus aureus (MRSA) shhsA1 | 8.0–64.0 μg/mL | 10.1021/acs.orglett.1c00328 Organic Letters |
| Antibacterial | MIC | Enterococcus faecalis ATCC 29212, Vibrio alginolyticus 13214 | 32.0 μg/mL | 10.1021/acs.orglett.1c00328 Organic Letters |
| Antitumor | IC50 | SF-268, HepG-2, A549, MCF-7 human cancer cell lines | 12.0–34.0 μM | 10.1021/acs.orglett.1c00328 Organic Letters |