1. Home
  2. Compounds
  3. 2-chloro-1,3,8-trihydroxy-6-(hydroxymethyl)anthracene-9,10-dione

SCS-C001282

2-chloro-1,3,8-trihydroxy-6-(hydroxymethyl)anthracene-9,10-dione

Pathway: Polyketides Superclass: Polycyclic aromatic polyketides Class: Anthraquinones and anthrones
Back to List

Chemical Structure

Structure of 2-chloro-1,3,8-trihydroxy-6-(hydroxymethyl)anthracene-9,10-dione
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Download: SDF SMILES

Source Information

Penicillium sp. SCSIO sof101 (soft coral-derived fungus)
Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species Penicillium sp. SCSIO SOF101
South China Sea  · -2448m  · 112°124′ E, 18°0.549′ N
DOI: 10.1021/acs.jnatprod.7b00269  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
320.7 Da
Threshold ≤ 500
ALogP
1.72
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C15H9ClO6
Molecular Weight:
320.6800 Da
SMILES:
O=C1c2cc(CO)cc(O)c2C(=O)c2c1cc(O)c(Cl)c2O
InChIKey:
GPTPSPAFUZTDEG-UHFFFAOYSA-N
InChI:
InChI=1S/C15H9ClO6/c16-12-9(19)3-7-11(15(12)22)14(21)10-6(13(7)20)1-5(4-17)2-8(10)18/h1-3,17-19,22H,4H2
Calculated Properties
ALogP:
1.724 lipophilicity
TPSA:
115.06 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
6
Rotatable Bonds:
1
Ring Count:
3 (2 aromatic)
Chiral Centers:
0
Fsp³:
0.0667 fraction sp³ carbon

Database Information

Compound ID:
SCS-C001282
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Polycyclic aromatic polyketides
NPClassifier Class:
Anthraquinones and anthrones
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

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 Jurkat/K562/HeLa cells > 10.0 μM 10.1021/acs.jnatprod.7b00269 Journal of Natural Products
Antitumor inhibition Jurkat/K562/HeLa cells 20μM (IL-2 inhibition) 10.1021/acs.jnatprod.7b00269 Journal of Natural Products
Back to Compounds
Structure enlarged