SCS-C001330
kebanmycin D
Pathway: Polyketides
Superclass: Polycyclic aromatic polyketides
Class: Anthraquinones and anthrones
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
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
502.5 Da
Threshold ≤ 500
ALogP
3.66
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
8
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C28H22O9
Molecular Weight:
502.4800 Da
SMILES:
CCCC(=O)Cc1cc2c(c(O)c1C(=O)O)-c1cc3c(c(O)c1CC2)C(=O)c1c(O)cc(O)cc1C3=O
InChIKey:
MZEFFODFPGBVNO-UHFFFAOYSA-N
InChI:
InChI=1S/C28H22O9/c1-2-3-13(29)7-12-6-11-4-5-15-16(20(11)26(34)21(12)28(36)37)10-18-23(25(15)33)27(35)22-17(24(18)32)8-14(30)9-19(22)31/h6,8-10,30-31,33-34H,2-5,7H2,1H3,(H,36,37)
Calculated Properties
ALogP:
3.660 lipophilicity
TPSA:
169.43 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
8
Rotatable Bonds:
5
Ring Count:
5
(3 aromatic)
Chiral Centers:
0
Fsp³:
0.2143 fraction sp³ carbon
Database Information
Compound ID:
SCS-C001330
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Polycyclic aromatic polyketides
NPClassifier Class:
Anthraquinones and anthrones
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 | 32.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA shhs-A1 | 16.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA 1862 | 16.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA 669 | 16.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA 991 | 16.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | B.subtilis 1064 | > 64.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |