SCS-C000429
paecilin C
Pathway: Polyketides
Superclass: Chromanes
Class: Chromones
Chemical Structure
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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
2.42
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
14
Threshold ≤ 10
2 violations (MW, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C32H30O14
Molecular Weight:
638.6000 Da
SMILES:
COC(=O)C1([C@@H]2OC(=O)C[C@@H]2C)CC(=O)c2c(O)ccc(-c3ccc(O)c4c3OC(C(=O)OC)([C@H]3OC(=O)C[C@@H]3C)CC4=O)c2O1
InChIKey:
UJORNCQXCUJGMA-BQQYPSOVSA-N
InChI:
InChI=1S/C32H30O14/c1-13-9-21(37)43-27(13)31(29(39)41-3)11-19(35)23-17(33)7-5-15(25(23)45-31)16-6-8-18(34)24-20(36)12-32(30(40)42-4,46-26(16)24)28-14(2)10-22(38)44-28/h5-8,13-14,27-28,33-34H,9-12H2,1-4H3/t13-,14-,27-,28+,31?,32?/m0/s1
Calculated Properties
ALogP:
2.422 lipophilicity
TPSA:
198.26 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
14
Rotatable Bonds:
5
Ring Count:
6
(2 aromatic)
Chiral Centers:
6
Fsp³:
0.4375 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000429
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Chromanes
NPClassifier Class:
Chromones
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 |