SCS-C001328
kebanmycin B
Pathway: Polyketides
Superclass: Polycyclic aromatic polyketides
Class: Anthraquinones and anthrones
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
582.6 Da
Threshold ≤ 500
ALogP
3.44
Threshold ≤ 5
H-Bond Donors
7
Threshold ≤ 5
H-Bond Acceptors
12
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C30H30O12
Molecular Weight:
582.5580 Da
SMILES:
CCCCC[C@@H](O)OC(=O)c1c(O)ccc2c1C[C@@H](O)c1c(O)c(OC)c3c(c1-2)C(O)Oc1cc(O)cc(O)c1C3=O
InChIKey:
QYPMNCFUPMINIX-KGIWVDMWSA-N
InChI:
InChI=1S/C30H30O12/c1-3-4-5-6-19(35)42-29(38)20-14-11-17(34)23-21(13(14)7-8-15(20)32)24-25(28(40-2)27(23)37)26(36)22-16(33)9-12(31)10-18(22)41-30(24)39/h7-10,17,19,30-35,37,39H,3-6,11H2,1-2H3/t17-,19+,30?/m1/s1
Calculated Properties
ALogP:
3.444 lipophilicity
TPSA:
203.44 Ų polar surface area
H-Bond Donors:
7
H-Bond Acceptors:
12
Rotatable Bonds:
7
Ring Count:
5
(3 aromatic)
Chiral Centers:
3
Fsp³:
0.3333 fraction sp³ carbon
Database Information
Compound ID:
SCS-C001328
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 | 2.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA shhs-A1 | 2.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA 1862 | 1.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA 669 | 2.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA 991 | 2.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | B.subtilis 1064 | 2.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antitumor | IC50 | HepG2 | 4.4 ± 0.1 μM | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antitumor | IC50 | MCF-7 | 1.8 ± 0.1 μM | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |