SCS-C008025
1-epi-arisugacin H
Pathway: Terpenoids
Superclass: Meroterpenoids
Class: Triketide meroterpenoids
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. SCSIO 41691
(soft coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
NA
Nansha Islands
· 9°39′29.75″N, 112°59′09.84″E
DOI:
10.1021/acs.jnatprod.3c01121
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
526.6 Da
Threshold ≤ 500
ALogP
2.75
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C29H34O9
Molecular Weight:
526.5820 Da
SMILES:
COc1ccc(-c2cc3c(c(=O)o2)C[C@@]2(O)[C@H](CC[C@]4(O)[C@]2(C)[C@@]2(O)CC[C@@]4(C)[C@H](OC(C)=O)C2)O3)cc1
InChIKey:
HMNRSYVWOLNBEB-HFUILWOPSA-N
InChI:
InChI=1S/C29H34O9/c1-16(30)36-23-15-27(32)12-11-25(23,2)29(34)10-9-22-28(33,26(27,29)3)14-19-21(37-22)13-20(38-24(19)31)17-5-7-18(35-4)8-6-17/h5-8,13,22-23,32-34H,9-12,14-15H2,1-4H3/t22-,23+,25-,26+,27+,28+,29+/m0/s1
Calculated Properties
ALogP:
2.748 lipophilicity
TPSA:
135.66 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
9
Rotatable Bonds:
3
Ring Count:
7
(2 aromatic)
Chiral Centers:
7
Fsp³:
0.5862 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008025
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Triketide 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 |
|---|---|---|---|---|
| Anti-inflammatory | IC50 | nitric oxide production | Compounds 1?9 were evaluated for their inhibitory activity against LPS activated NO production in RAW 264.7 cells. The results (Table 4) showed that only 5 significantly inhibited NO production | 10.1021/acs.jnatprod.3c01121 Journal of Natural Products |
| Antitumor | — | human lung adenocarcinoma cell line H1975 | In addition, all of the tested compounds did not show obvious cytotoxicity against human lung adenocarcinoma cell line H1975 (Table 4). | 10.1021/acs.jnatprod.3c01121 Journal of Natural Products |