SCS-C008003
6,16-O-dideacetylhelvolic acid 21,16-lactone
Pathway: Terpenoids
Superclass: Triterpenoids
Class: Fusidane triterpenoids
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
Aspergillus fumigatus HNMF0047
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus fumigatus
South China Sea
DOI:
10.1021/acs.jnatprod.8b00382
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
466.6 Da
Threshold ≤ 500
ALogP
4.74
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C29H38O5
Molecular Weight:
466.6180 Da
SMILES:
CC(C)=CCCC1=C2[C@H](C[C@@]3(C)[C@H]2CC[C@H]2[C@@]4(C)C=CC(=O)[C@@H](C)[C@@H]4[C@H](O)C(=O)[C@@]23C)OC1=O
InChIKey:
CZLFAMRWSRZRHF-IDTZKTCDSA-N
InChI:
InChI=1S/C29H38O5/c1-15(2)8-7-9-17-22-18-10-11-21-27(4)13-12-19(30)16(3)23(27)24(31)25(32)29(21,6)28(18,5)14-20(22)34-26(17)33/h8,12-13,16,18,20-21,23-24,31H,7,9-11,14H2,1-6H3/t16-,18+,20+,21+,23-,24+,27-,28+,29-/m1/s1
Calculated Properties
ALogP:
4.738 lipophilicity
TPSA:
80.67 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
5
Rotatable Bonds:
3
Ring Count:
5
(0 aromatic)
Chiral Centers:
9
Fsp³:
0.6897 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008003
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Triterpenoids
NPClassifier Class:
Fusidane triterpenoids
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 | Staphylococcus aureus | > 128.0 μg/mL | 10.1021/acs.jnatprod.8b00382 Journal of Natural Products |
| Antibacterial | MIC | Escherichia coli | > 128.0 μg/mL | 10.1021/acs.jnatprod.8b00382 Journal of Natural Products |
| Antibacterial | MIC | Bacillus subtilis | > 128.0 μg/mL | 10.1021/acs.jnatprod.8b00382 Journal of Natural Products |
| Antibacterial | MIC | Streptococcus agalactiae | > 128.0 μg/mL | 10.1021/acs.jnatprod.8b00382 Journal of Natural Products |