SCS-C007869
geldanamycin
Pathway: Polyketides
Superclass: Macrolides
Class: Ansa macrolides
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 malaysiensis
(NA)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces malaysiensis
South China Sea
DOI:
10.1021/acs.jnatprod.1c00297
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
560.6 Da
Threshold ≤ 500
ALogP
2.41
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C29H40N2O9
Molecular Weight:
560.6440 Da
SMILES:
COC1=C2C[C@@H](C)C[C@H](OC)[C@H](O)[C@@H](C)/C=C(\C)[C@H](OC(N)=O)[C@@H](OC)/C=C\C=C(/C)C(=O)NC(=CC1=O)C2=O
InChIKey:
QTQAWLPCGQOSGP-KSRBKZBZSA-N
InChI:
InChI=1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,16-9+,18-13+/t15-,17+,22+,23+,24-,26+/m1/s1
Calculated Properties
ALogP:
2.408 lipophilicity
TPSA:
163.48 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
9
Rotatable Bonds:
4
Ring Count:
2
(0 aromatic)
Chiral Centers:
6
Fsp³:
0.5172 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007869
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Macrolides
NPClassifier Class:
Ansa macrolides
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 |
|---|---|---|---|---|
| Antitumor | IC50 | C42B (prostate cancer cell line) | 0.5 μM | 10.1021/acs.jnatprod.1c00297 Journal of Natural Products |
| Antitumor | IC50 | 22RV1 (prostate cancer cell line) | 0.85 μM | 10.1021/acs.jnatprod.1c00297 Journal of Natural Products |