SCS-C001329
kebanmycin C
Pathway: Polyketides
Superclass: Polycyclic aromatic polyketides
Class: Ericamycins
Glycoside
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
666.6 Da
Threshold ≤ 500
ALogP
2.94
Threshold ≤ 5
H-Bond Donors
7
Threshold ≤ 5
H-Bond Acceptors
14
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C34H34O14
Molecular Weight:
666.6300 Da
SMILES:
CCC[C@@H]1Cc2cc3c(c(O)c2C(=O)O1)-c1c(c(OC)c2oc4ccc(O[C@H]5CC(O)[C@H](O)[C@@H](C)O5)c(O)c4c(=O)c2c1O)[C@H](O)[C@H]3O
InChIKey:
NYZAOHCLSQGQLH-VCIVKJPESA-N
InChI:
InChI=1S/C34H34O14/c1-4-5-13-8-12-9-14-20(28(39)19(12)34(43)46-13)22-23(31(42)26(14)37)32(44-3)33-24(30(22)41)29(40)21-16(48-33)6-7-17(27(21)38)47-18-10-15(35)25(36)11(2)45-18/h6-7,9,11,13,15,18,25-26,31,35-39,41-42H,4-5,8,10H2,1-3H3/t11-,13-,15?,18+,25-,26+,31+/m1/s1
Calculated Properties
ALogP:
2.936 lipophilicity
TPSA:
225.81 Ų polar surface area
H-Bond Donors:
7
H-Bond Acceptors:
14
Rotatable Bonds:
5
Ring Count:
7
(4 aromatic)
Chiral Centers:
7
Fsp³:
0.4118 fraction sp³ carbon
Database Information
Compound ID:
SCS-C001329
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Polycyclic aromatic polyketides
NPClassifier Class:
Ericamycins
Glycoside:
Yes
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 | 0.5 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antibacterial | MIC | MRSA shhs-A1 | 0.5 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 | 4.0 μg/mL | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antitumor | IC50 | HepG2 | 31.0 ± 1.0 μM | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |
| Antitumor | IC50 | MCF-7 | 0.76 ± 0.01 μM | 10.1021/acs.jnatprod.4c00232 Journal of Natural Products |