SCS-C007243
ergost-4,24(28)-diene-3-one
Pathway: Terpenoids
Superclass: Steroids
Class: Ergostane steroids
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
Sinularia depressa
(soft coral)
Original source name: Sinularia depressa Tixier-Durivault
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Malacalcyonacea
Family
Sinulariidae
Genus
Sinularia
Species
Sinularia depressa
South China Sea
DOI:
10.1016/j.bmcl.2012.12.087
· Bioorganic & Medicinal Chemistry Letters
Drug-likeness (Lipinski Ro5)
Molecular Weight
396.7 Da
Threshold ≤ 500
ALogP
7.76
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
1
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C28H44O
Molecular Weight:
396.6590 Da
SMILES:
C=C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C
InChIKey:
JRMPVNVOLQJLJX-QVMRCSLBSA-N
InChI:
InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h17-18,20,23-26H,3,7-16H2,1-2,4-6H3/t20-,23+,24-,25+,26+,27+,28-/m1/s1
Calculated Properties
ALogP:
7.763 lipophilicity
TPSA:
17.07 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
1
Rotatable Bonds:
5
Ring Count:
4
(0 aromatic)
Chiral Centers:
7
Fsp³:
0.8214 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007243
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Ergostane steroids
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 |
|---|---|---|---|---|
| Enzyme inhibition | IC50 | human protein tyrosine phosphatase 1B (PTP1B) | 15.3 μM | 10.1016/j.bmcl.2012.12.087 Bioorganic & Medicinal Chemistry Letters |
| Neuroprotective / Neuromodulatory | cell viability increase | β-amyloid-25-35 (Aβ25-35) induced cellular injuries | 16.6 % | 10.1016/j.bmcl.2012.12.087 Bioorganic & Medicinal Chemistry Letters |
| Neuroprotective / Neuromodulatory | cell viability increase | serum deprivation-induced injuries | 16.9 % | 10.1016/j.bmcl.2012.12.087 Bioorganic & Medicinal Chemistry Letters |