SCS-C005883
penicilliumin A
Pathway: Polyketides | Terpenoids
Superclass: Meroterpenoids | Sesquiterpenoids
Class: Drimane sesquiterpenoids | Tetraketide meroterpenoids
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. F00120
(soft coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
NA
South China Sea
· 1300 m
· Lat. 22°6.017N, Long. 119°17.440'E
DOI:
10.3390/md10010106
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
360.5 Da
Threshold ≤ 500
ALogP
3.37
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H32O4
Molecular Weight:
360.4940 Da
SMILES:
C=C1CC[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1CC1(O)CC(=O)C(CO)=CC1=O
InChIKey:
WNDYBUMSCQZGJO-SPRYDSOMSA-N
InChI:
InChI=1S/C22H32O4/c1-14-6-7-18-20(2,3)8-5-9-21(18,4)16(14)11-22(26)12-17(24)15(13-23)10-19(22)25/h10,16,18,23,26H,1,5-9,11-13H2,2-4H3/t16-,18-,21+,22?/m0/s1
Calculated Properties
ALogP:
3.367 lipophilicity
TPSA:
74.60 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
4
Rotatable Bonds:
3
Ring Count:
3
(0 aromatic)
Chiral Centers:
4
Fsp³:
0.7273 fraction sp³ carbon
Database Information
Compound ID:
SCS-C005883
NPClassifier Pathway:
Polyketides
Terpenoids
NPClassifier Superclass:
Meroterpenoids
Sesquiterpenoids
NPClassifier Class:
Drimane sesquiterpenoids
Tetraketide meroterpenoids
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 |
|---|---|---|---|---|
| Antitumor | GL50 | human melanoma cells | 22.88 μg/mL | 10.3390/md10010106 Marine Drugs |
| Antitumor | GL50 | mouse melanoma cells | 27.37 μg/mL | 10.3390/md10010106 Marine Drugs |
| Antitumor | GL50 | human cervical carcinoma cells | 44.05 μg/mL | 10.3390/md10010106 Marine Drugs |
| Antitumor | TC50 | human cervical carcinoma cells | 40.72 μg/mL | 10.3390/md10010106 Marine Drugs |
| Antitumor | TC50 | African green monkey kidney cells | 133.52 μg/mL | 10.3390/md10010106 Marine Drugs |
| Antitumor | TC50 | Madin-Darby canine kidney cells | 43.0 μg/mL | 10.3390/md10010106 Marine Drugs |