SCS-C001331
FD594 aglycon
Pathway: Polyketides
Superclass: Polycyclic aromatic polyketides
Chemical Structure
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Streptomyces sp. SCSIO 40068
(bacterium)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
NA
Gaoqiao
· E 109.7595°, N 21.5676°
DOI:
10.1021/acs.jnatprod.4c00232
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
552.5 Da
Threshold ≤ 500
ALogP
3.12
Threshold ≤ 5
H-Bond Donors
7
Threshold ≤ 5
H-Bond Acceptors
11
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C29H28O11
Molecular Weight:
552.5320 Da
SMILES:
CCCCC(O)C(=O)c1c(O)ccc2c1C[C@@H](O)c1c(O)c(OC)c3c(c1-2)C(O)Oc1cc(O)cc(O)c1C3=O
InChIKey:
REOFQSAWESDEIB-NSRJXDANSA-N
InChI:
InChI=1S/C29H28O11/c1-3-4-5-15(32)25(35)19-13-10-17(34)22-20(12(13)6-7-14(19)31)23-24(28(39-2)27(22)37)26(36)21-16(33)8-11(30)9-18(21)40-29(23)38/h6-9,15,17,29-34,37-38H,3-5,10H2,1-2H3/t15?,17-,29?/m1/s1
Calculated Properties
ALogP:
3.122 lipophilicity
TPSA:
194.21 Ų polar surface area
H-Bond Donors:
7
H-Bond Acceptors:
11
Rotatable Bonds:
6
Ring Count:
5
(3 aromatic)
Chiral Centers:
3
Fsp³:
0.3103 fraction sp³ carbon
Database Information
Compound ID:
SCS-C001331
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Polycyclic aromatic polyketides
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 | S.aureus ATCC29213 | 8.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA shhs-A1 | 8.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA 1862 | 4.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA 669 | 8.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA 991 | 8.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | B.subtilis 1064 | 16.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antitumor | IC50 | HepG2 | 13.0 ± 1.0 μM | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antitumor | IC50 | MCF-7 | 0.46 ± 0.01 μM | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |