SCS-C006914
aspermeroterpene B
Pathway: Polyketides | Terpenoids
Superclass: Meroterpenoids
Class: Tetraketide 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
Aspergillus terreus GZU-31-1
(mangrove endophytic fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus terreus
South China Sea
DOI:
10.1016/j.phytochem.2024.113983
· Phytochemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
528.6 Da
Threshold ≤ 500
ALogP
2.36
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
10
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C28H32O10
Molecular Weight:
528.5540 Da
SMILES:
C=C1[C@@H](OC(C)=O)[C@@H]2[C@](C)(C(=O)C(O)=C3C(C)(C)C(=O)C=C[C@]32C)[C@]2(C(=O)OC)C(=O)[C@@H](C)OC(=O)[C@]12C
InChIKey:
CDQXYTLYCDABPX-FYGPHMSISA-N
InChI:
InChI=1S/C28H32O10/c1-12-17(38-14(3)29)19-25(6)11-10-15(30)24(4,5)18(25)16(31)21(33)27(19,8)28(23(35)36-9)20(32)13(2)37-22(34)26(12,28)7/h10-11,13,17,19,31H,1H2,2-9H3/t13-,17-,19+,25-,26+,27-,28+/m1/s1
Calculated Properties
ALogP:
2.357 lipophilicity
TPSA:
150.34 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
10
Rotatable Bonds:
2
Ring Count:
4
(0 aromatic)
Chiral Centers:
7
Fsp³:
0.5714 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006914
NPClassifier Pathway:
Polyketides
Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Tetraketide 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 |
|---|---|---|---|---|
| Antifibrotic / Organ protection | inhibition of α-SMA mRNA expression | α-SMA | — Structured numeric value is not available in this record; see the primary reference. | 10.1016/j.phytochem.2024.113983 Phytochemistry |
| Receptor / Signaling modulation | inhibition of HSCs activation | Nrf2 signaling | 10 exerts a potent inhibitory effect on the activation of HSCs in vitro | 10.1016/j.phytochem.2024.113983 Phytochemistry |
| Antifibrotic / Organ protection | inhibition of ECM deposition | TGF-β1, COL1A1, TIMP-1 | — Structured numeric value is not available in this record; see the primary reference. | 10.1016/j.phytochem.2024.113983 Phytochemistry |
| Cellular modulation | induction of apoptosis | PARP | — Structured numeric value is not available in this record; see the primary reference. | 10.1016/j.phytochem.2024.113983 Phytochemistry |
| Antioxidant | inhibition of ROS production | ROS | — Structured numeric value is not available in this record; see the primary reference. | 10.1016/j.phytochem.2024.113983 Phytochemistry |
| Receptor / Signaling modulation | upregulation of Nrf2 and downstream proteins | Nrf2, HO-1, NQO1 | — Structured numeric value is not available in this record; see the primary reference. | 10.1016/j.phytochem.2024.113983 Phytochemistry |