SCS-C004493
(1'S)-1'-O-methyl-7-chloroaverantin
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
Aspergillus sp.
(coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
NA
South China Sea
DOI:
10.1021/np3002699
· Journal of Natural Products
Aspergillus sp.
(coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
NA
South China Sea
· 1138 m
DOI:
10.3390/md24060214
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
420.8 Da
Threshold ≤ 500
ALogP
4.21
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C21H21ClO7
Molecular Weight:
420.8450 Da
SMILES:
CCCCC[C@H](OC)c1c(O)cc2c(c1O)C(=O)c1c(cc(O)c(Cl)c1O)C2=O
InChIKey:
KGTDNRSYXXWABH-ZDUSSCGKSA-N
InChI:
InChI=1S/C21H21ClO7/c1-3-4-5-6-13(29-2)16-11(23)7-9-14(20(16)27)19(26)15-10(18(9)25)8-12(24)17(22)21(15)28/h7-8,13,23-24,27-28H,3-6H2,1-2H3/t13-/m0/s1
Calculated Properties
ALogP:
4.206 lipophilicity
TPSA:
124.29 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
7
Rotatable Bonds:
6
Ring Count:
3
(2 aromatic)
Chiral Centers:
1
Fsp³:
0.3333 fraction sp³ carbon
Database Information
Compound ID:
SCS-C004493
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 |
|---|---|---|---|---|
| Antitumor | IC50 | HT29 colon cancer cells | 19.17 μM | 10.3390/md24060214 Marine Drugs |
| Antitumor | IC50 | 293T non-tumor cells | 27.73 μM | 10.3390/md24060214 Marine Drugs |
| Antitumor | colony formation inhibition | HT29 colon cancer cells | Compound 4 at 5 and 10 μM significantly reduced relative colony area without markedly affecting colony number, indicating impaired colony expansion | 10.3390/md24060214 Marine Drugs |
| Antitumor | apoptotic cell proportion increase | HT29 colon cancer cells | — Structured numeric value is not available in this record; see the primary reference. | 10.3390/md24060214 Marine Drugs |