1. Home
  2. Compounds
  3. 2-hydroxy-16,18-dimethoxy-7,9-dioxapentacyclo[10.8.0.03,10.04,8.014,19]icosa-1,3(10),11,14(19),15,17-hexaene-13,20-dione

SCS-C000059

2-hydroxy-16,18-dimethoxy-7,9-dioxapentacyclo[10.8.0.03,10.04,8.014,19]icosa-1,3(10),11,14(19),15,17-hexaene-13,20-dione

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

Chemical Structure

Structure of 2-hydroxy-16,18-dimethoxy-7,9-dioxapentacyclo[10.8.0.03,10.04,8.014,19]icosa-1,3(10),11,14(19),15,17-hexaene-13,20-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

fungal sp. ZSUH-36 (mangrove endophytic fungus)
Original source name: mangrove endophytic fungus ZSUH-36 (isolated from the Shenzhen mangrove Acanthus ilicifolius Linn.)
Kingdom Fungi Phylum Ascomycota Class NA Order NA Family NA Genus NA Species NA
South China Sea
DOI: 10.1002/mrc.1974  · Magnetic Resonance in Chemistry
N/A
South China Sea
DOI: 10.3390/md8041094  · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight
368.3 Da
Threshold ≤ 500
ALogP
2.41
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C20H16O7
Molecular Weight:
368.3410 Da
SMILES:
COc1cc(OC)c2c(c1)C(=O)c1cc3c(c(O)c1C2=O)C1CCOC1O3
InChIKey:
NZRQTYSAMANXPT-UHFFFAOYSA-N
InChI:
InChI=1S/C20H16O7/c1-24-8-5-10-15(12(6-8)25-2)19(23)16-11(17(10)21)7-13-14(18(16)22)9-3-4-26-20(9)27-13/h5-7,9,20,22H,3-4H2,1-2H3
Calculated Properties
ALogP:
2.407 lipophilicity
TPSA:
91.29 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
7
Rotatable Bonds:
2
Ring Count:
5 (2 aromatic)
Chiral Centers:
2
Fsp³:
0.3000 fraction sp³ carbon

Database Information

Compound ID:
SCS-C000059
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 KB, KBv200, MCF-7, MCF-7/adr, A549, LO2 IC50 (μmol/L): all >50 10.3390/md8041094 Marine Drugs
Back to Compounds
Structure enlarged