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SCS-C006791

3β-hydroxy-(22E,24R)-ergosta-5,8,22-trien-7-one

Pathway: Terpenoids Superclass: Steroids Class: Ergostane steroids
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Chemical Structure

Structure of 3β-hydroxy-(22E,24R)-ergosta-5,8,22-trien-7-one
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Download: SDF SMILES

Source Information

Pestalotiopsis sp. (coral-associated fungus)
Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Amphisphaeriales Family Sporocadaceae Genus Pestalotiopsis Species NA
South China Sea
DOI: 10.3390/md20110711  · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight
410.6 Da
Threshold ≤ 500
ALogP
6.65
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C28H42O2
Molecular Weight:
410.6420 Da
SMILES:
CC(C)[C@@H](C)/C=C/[C@@H](C)C1CCC2C3=C(CC[C@@]21C)[C@@]1(C)CC[C@H](O)CC1=CC3=O
InChIKey:
UOHNARRKDSHFLD-IAJVBNCBSA-N
InChI:
InChI=1S/C28H42O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-26-24(12-14-28(22,23)6)27(5)13-11-21(29)15-20(27)16-25(26)30/h7-8,16-19,21-23,29H,9-15H2,1-6H3/b8-7+/t18-,19+,21-,22?,23?,27-,28+/m0/s1
Calculated Properties
ALogP:
6.654 lipophilicity
TPSA:
37.30 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
2
Rotatable Bonds:
4
Ring Count:
4 (0 aromatic)
Chiral Centers:
7
Fsp³:
0.7500 fraction sp³ carbon

Database Information

Compound ID:
SCS-C006791
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Ergostane steroids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

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 NO production inhibition LPS-stimulated RAW 264.7 cells — Structured numeric value is not available in this record; see the primary reference. 10.3390/md20110711 Marine Drugs
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Structure enlarged