SCS-C002155
(7R,11S)-(+)-12-hydroxysydonic acid
Pathway: Terpenoids
Superclass: Sesquiterpenoids
Class: Bisabolane sesquiterpenoids
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
Aspergillus sp. XS-2009-0066
(coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
NA
Xisha Islands
2015.
Aspergillus sydowii
(coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus sydowii
South China Sea
DOI:
10.1016/j.fitote.2019.03.031
· Fitoterapia
Drug-likeness (Lipinski Ro5)
Molecular Weight
282.0 Da
Threshold ≤ 500
ALogP
2.10
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C15H22O5
Molecular Weight:
282.0000 Da
SMILES:
C[C@H](CO)CCC[C@](C)(O)c1ccc(C(=O)O)cc1O
InChIKey:
ISHXRANDGDVGJS-BONVTDFDSA-N
InChI:
InChI=1S/C15H22O5/c1-10(9-16)4-3-7-15(2,20)12-6-5-11(14(18)19)8-13(12)17/h5-6,8,10,16-17,20H,3-4,7,9H2,1-2H3,(H,18,19)/t10-,15-/m0/s1
Calculated Properties
ALogP:
2.097 lipophilicity
TPSA:
97.99 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
4
Rotatable Bonds:
7
Ring Count:
1
(1 aromatic)
Chiral Centers:
2
Fsp³:
0.5333 fraction sp³ carbon
Database Information
Compound ID:
SCS-C002155
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesquiterpenoids
NPClassifier Class:
Bisabolane sesquiterpenoids
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 | K. rhizophila | 6.25 μg/mL | — |
| Antibacterial | — | Methicillin-resistant Staphyloccocus aureus; Staphyloccocus aureus; Enterococcus faecalis; Escherichia coli; Klebsiella pneumoniae | none of compounds showed antibacterial and cytotoxic activities | 10.1016/j.fitote.2019.03.031 Fitoterapia |
| Antitumor | — | K562; SGC-7901; A549; Hela cell lines | none of compounds showed antibacterial and cytotoxic activities | 10.1016/j.fitote.2019.03.031 Fitoterapia |
| Antitumor | — | MDCK cells | > 200.0 μM | 10.1016/j.fitote.2019.03.031 Fitoterapia |