SCS-C000557
nafuredin
Pathway: Polyketides
Superclass: Linear polyketides
Class: Open-chain polyketides
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
Talaromyces sp.
(soft coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Trichocomaceae
Genus
Talaromyces
Species
NA
South China Sea
DOI:
10.3390/md23080329
· Marine Drugs
Trichoderma harzianum
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Hypocreales
Family
Hypocreaceae
Genus
Trichoderma
Species
Trichoderma harzianum
South China Sea
DOI:
10.1080/10286020.2020.1729752
· Journal of Asian Natural Products Research
Drug-likeness (Lipinski Ro5)
Molecular Weight
360.5 Da
Threshold ≤ 500
ALogP
4.12
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H32O4
Molecular Weight:
360.5000 Da
SMILES:
CC[C@H](C)/C=C/C=C(\C)C[C@@H](C)/C=C/C=C/[C@H]1OC(=O)[C@H](O)[C@@H]2O[C@]12C
InChIKey:
NMEGHQQRWKBPQO-IMNRXHEYSA-N
InChI:
InChI=1S/C22H32O4/c1-6-15(2)11-9-12-17(4)14-16(3)10-7-8-13-18-22(5)20(26-22)19(23)21(24)25-18/h7-13,15-16,18-20,23H,6,14H2,1-5H3/b10-7+,11-9+,13-8+,17-12+/t15-,16-,18+,19+,20-,22+/m0/s1
Calculated Properties
ALogP:
4.117 lipophilicity
TPSA:
59.06 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
4
Rotatable Bonds:
8
Ring Count:
2
(0 aromatic)
Chiral Centers:
6
Fsp³:
0.5909 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000557
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Linear polyketides
NPClassifier Class:
Open-chain polyketides
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 |
|---|---|---|---|---|
| Antifouling | EC50 | Bugula neritina larva settlement | 21.4 μg/mL | 10.1080/10286020.2020.1729752 Journal of Asian Natural Products Research |
| Antitumor | IC50 | HepG2 cells | 303.6 μM | 10.3390/md23080329 Marine Drugs |
| Antitumor | — | Figure 5C | Subsequent validation in HepG2 cells treated with compound 3 (100 μM,24 h)) revealed robust upregulation of core ferroptosis regulatory genes—NRF2, SLC7A11, FTH1, HMOX1, GCLC, and GCLM—via RT-qPCR analysis (Figure 5C). | 10.3390/md23080329 Marine Drugs |
| Antifibrotic / Organ protection | — | AML12 cell oxygen-glucose deprivation/reperfusion (OGD/R) injury model | Nafuredin A (3) significantly attenuated OGD/R-induced cytotoxicity in a concentration-dependent manner, as evidenced by the restoration of cellular viability (Figure 6A). | 10.3390/md23080329 Marine Drugs |
| Antifibrotic / Organ protection | — | Murine hepatic ischemia-reperfusion injury (HIRI) model | — Structured numeric value is not available in this record; see the primary reference. | 10.3390/md23080329 Marine Drugs |
| Receptor / Signaling modulation | binding score | KEAP1-NRF2 complex | -5.352 kcal/mol | 10.3390/md23080329 Marine Drugs |