SCS-C008260
diproximicin A
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
Verrucosispora sp.
(NA)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Micromonosporales
Family
Micromonosporaceae
Genus
Verrucosispora
Species
NA
South China Sea
· 227.02 m
· E 119°29′998″, N 22°30′181″
DOI:
10.1021/acs.jnatprod.9b01185
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
654.6 Da
Threshold ≤ 500
ALogP
4.25
Threshold ≤ 5
H-Bond Donors
6
Threshold ≤ 5
H-Bond Acceptors
12
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C29H30N6O12
Molecular Weight:
654.5890 Da
SMILES:
COC(=O)Nc1coc(C(=O)Nc2coc(C(=O)NCCCCCNC(=O)c3cc(NC(=O)c4cc(NC(=O)OC)co4)co3)c2)c1
InChIKey:
RFSIKVSNRXDLSP-UHFFFAOYSA-N
InChI:
InChI=1S/C29H30N6O12/c1-42-28(40)34-18-10-22(46-14-18)26(38)32-16-8-20(44-12-16)24(36)30-6-4-3-5-7-31-25(37)21-9-17(13-45-21)33-27(39)23-11-19(15-47-23)35-29(41)43-2/h8-15H,3-7H2,1-2H3,(H,30,36)(H,31,37)(H,32,38)(H,33,39)(H,34,40)(H,35,41)
Calculated Properties
ALogP:
4.250 lipophilicity
TPSA:
245.62 Ų polar surface area
H-Bond Donors:
6
H-Bond Acceptors:
12
Rotatable Bonds:
14
Ring Count:
4
(4 aromatic)
Chiral Centers:
0
Fsp³:
0.2414 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008260
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 |
|---|---|---|---|---|
| Antibacterial | MIC | Staphylococcus aureus ATCC 29213; methicillin-resistant Staphylococcus aureus shhs-A1 | Compounds 1?5 were evaluated for their antibacterial activities against four indicator strains... | 10.1021/acs.jnatprod.9b01185 Journal of Natural Products |
| Enzyme inhibition | inhibition | α-glucosidase; tyrosinase; acetylcholinesterase | Compounds 1?5 were also tested for their inhibitory activities toward α-glucosidase, tyrosinase, and acetylcholinesterase. However, compounds 1?5 failed to exhibit enzyme inhibitory activities | 10.1021/acs.jnatprod.9b01185 Journal of Natural Products |
| Antitumor | IC50 | SF-268, MCF-7, HepG-2, A549 human cancer cell lines | > 10.0 μM | 10.1021/acs.jnatprod.9b01185 Journal of Natural Products |