SCS-C001361
13-Dimethoxy glucopiericidin A
Pathway: Polyketides
Glycoside
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 psammoticus
(Streptomyces)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces psammoticus
Pearl River Estuary
· -5m
· E 113°33′11.15″, N22°53′40.16″
DOI:
10.1021/acs.jmedchem.9b00598
· Journal of Medicinal Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
637.8 Da
Threshold ≤ 500
ALogP
2.47
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
11
Threshold ≤ 10
2 violations (MW, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C33H51NO11
Molecular Weight:
637.8000 Da
SMILES:
COc1[nH]c(C/C=C(\C)C/C=C/C(C)=C/[C@@H](C)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)/C(C)=C/C(OC)OC)c(C)c(=O)c1OC
InChIKey:
ZJVOACHGLZFOII-SWSUXQPCSA-N
InChI:
InChI=1S/C33H51NO11/c1-18(13-14-23-22(5)26(36)31(42-8)32(34-23)43-9)11-10-12-19(2)15-20(3)30(21(4)16-25(40-6)41-7)45-33-29(39)28(38)27(37)24(17-35)44-33/h10,12-13,15-16,20,24-25,27-30,33,35,37-39H,11,14,17H2,1-9H3,(H,34,36)/b12-10+,18-13+,19-15+,21-16+/t20-,24-,27-,28+,29-,30-,33+/m1/s1
Calculated Properties
ALogP:
2.468 lipophilicity
TPSA:
169.16 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
11
Rotatable Bonds:
16
Ring Count:
2
(1 aromatic)
Chiral Centers:
7
Fsp³:
0.6061 fraction sp³ carbon
Database Information
Compound ID:
SCS-C001361
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
N/A
NPClassifier Class:
N/A
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 |
|---|---|---|---|---|
| Antitumor | — | Peroxiredoxin 1 (PRDX1) | Cytotoxicity against renal carcinoma cells | 10.1021/acs.jmedchem.9b00598 Journal of Medicinal Chemistry |