SCS-C004890
macrosporin 2-O-(6′-acetyl)-α-D-glucopyranoside
Pathway: Polyketides
Superclass: Polycyclic aromatic polyketides
Class: Anthraquinones and anthrones
Glycoside
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
Stemphylium sp.
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Dothideomycetes
Order
Pleosporales
Family
Pleosporaceae
Genus
Stemphylium
Species
NA
South China Sea
DOI:
10.1021/np500340y
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
488.4 Da
Threshold ≤ 500
ALogP
0.23
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
11
Threshold ≤ 10
1 violation (HBA) — borderline drug-like
Chemical Properties
Molecular Formula:
C24H24O11
Molecular Weight:
488.4450 Da
SMILES:
COc1cc(O)c2c(c1)C(=O)c1cc(C)c(O[C@H]3O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]3O)cc1C2=O
InChIKey:
SIAFXYFDIILGJD-JCTDHXFVSA-N
InChI:
InChI=1S/C24H24O11/c1-9-4-12-13(20(28)18-14(19(12)27)5-11(32-3)6-15(18)26)7-16(9)34-24-23(31)22(30)21(29)17(35-24)8-33-10(2)25/h4-7,17,21-24,26,29-31H,8H2,1-3H3/t17-,21-,22+,23-,24+/m1/s1
Calculated Properties
ALogP:
0.234 lipophilicity
TPSA:
169.05 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
11
Rotatable Bonds:
5
Ring Count:
4
(2 aromatic)
Chiral Centers:
5
Fsp³:
0.3750 fraction sp³ carbon
Database Information
Compound ID:
SCS-C004890
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Polycyclic aromatic polyketides
NPClassifier Class:
Anthraquinones and anthrones
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.