SCS-C000432
penicillixanthone A
Pathway: Polyketides
Superclass: Xanthones | Polycyclic aromatic polyketides
Class: Anthraquinones and anthrones | Methyl xanthones
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
Penicillium sp. SCSGAF 0023
(soft coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
NA
South China Sea
DOI:
10.1038/ja.2012.110
· The Journal of Antibiotics
Drug-likeness (Lipinski Ro5)
Molecular Weight
638.6 Da
Threshold ≤ 500
ALogP
1.85
Threshold ≤ 5
H-Bond Donors
6
Threshold ≤ 5
H-Bond Acceptors
14
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C32H30O14
Molecular Weight:
638.6000 Da
SMILES:
COC(=O)[C@]12Oc3ccc(-c4ccc(O)c5c4O[C@@]4(C(=O)OC)C(=C5O)C(=O)C[C@@H](C)[C@@H]4O)c(O)c3C(O)=C1C(=O)C[C@@H](C)[C@@H]2O
InChIKey:
MWYDTJPKJVWDTM-ZKHWAINJSA-N
InChI:
InChI=1S/C32H30O14/c1-11-9-17(35)22-25(38)20-18(45-31(22,27(11)39)29(41)43-3)8-6-13(23(20)36)14-5-7-15(33)19-24(37)21-16(34)10-12(2)28(40)32(21,30(42)44-4)46-26(14)19/h5-8,11-12,27-28,33,36-40H,9-10H2,1-4H3/t11-,12-,27+,28+,31+,32+/m1/s1
Calculated Properties
ALogP:
1.851 lipophilicity
TPSA:
226.58 Ų polar surface area
H-Bond Donors:
6
H-Bond Acceptors:
14
Rotatable Bonds:
3
Ring Count:
6
(2 aromatic)
Chiral Centers:
6
Fsp³:
0.3750 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000432
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Xanthones
Polycyclic aromatic polyketides
NPClassifier Class:
Anthraquinones and anthrones
Methyl xanthones
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 |
|---|---|---|---|---|
| Antibacterial | MIC | Micrococcus luteus, Pseudomonas nigrifaciens, E. coli, B. subtilis | 24.4–390.5 μg/mL | 10.1038/ja.2012.110 The Journal of Antibiotics |