SCS-C007090
piperochromenoic acid
Pathway: Terpenoids
Superclass: Meroterpenoids
Class: Merosesquiterpenoids
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
Pestalotiopsis neglecta
(SCSIO41403)
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Amphisphaeriales
Family
Sporocadaceae
Genus
Pestalotiopsis
Species
Pestalotiopsis neglecta
South China Sea
DOI:
10.1016/j.bioorg.2021.104927
· Bioorganic Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
340.5 Da
Threshold ≤ 500
ALogP
6.02
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C22H28O3
Molecular Weight:
340.4630 Da
SMILES:
CC(C)=CCC/C(C)=C/CC[C@@]1(C)C=Cc2cc(C(=O)O)ccc2O1
InChIKey:
MSDAWPKHHPLFBC-IXNCKXOBSA-N
InChI:
InChI=1S/C22H28O3/c1-16(2)7-5-8-17(3)9-6-13-22(4)14-12-18-15-19(21(23)24)10-11-20(18)25-22/h7,9-12,14-15H,5-6,8,13H2,1-4H3,(H,23,24)/b17-9+/t22-/m0/s1
Calculated Properties
ALogP:
6.022 lipophilicity
TPSA:
46.53 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
2
Rotatable Bonds:
7
Ring Count:
2
(1 aromatic)
Chiral Centers:
1
Fsp³:
0.4091 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007090
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Merosesquiterpenoids
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 | IC50 | ACHN, OS-RC-2, 786-O, HL-60, K-562, MOLT-4, HepG2 cancer cell lines | > 50.0 μM | 10.1016/j.bioorg.2021.104927 Bioorganic Chemistry |
| Metabolic / Lipid regulation | mRNA level regulation | ABCA1, LXRβ | the downstream gene ABCA1 and LXRβ were significantly upregulated by 3 | 10.1016/j.bioorg.2021.104927 Bioorganic Chemistry |