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SCS-C007544

17β,20β-epoxy-23,24-dimethylcholest-5-ene-3β,22-diol

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

Structure of 17β,20β-epoxy-23,24-dimethylcholest-5-ene-3β,22-diol
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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.
Download: SDF SMILES

Source Information

Lobophytum sp. (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Alcyoniidae Genus Lobophytum Species NA
South China Sea  · -20 m
DOI: 10.1002/cbdv.202000214  · Chemistry & Biodiversity

Drug-likeness (Lipinski Ro5)

Molecular Weight
444.7 Da
Threshold ≤ 500
ALogP
6.13
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C29H48O3
Molecular Weight:
444.7000 Da
SMILES:
CC(C)[C@@H](C)[C@H](C)[C@@H](O)[C@]1(C)O[C@]12CC[C@H]1[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]12C
InChIKey:
CIBBJGAKYYGAAG-ANYPVYNQSA-N
InChI:
InChI=1S/C29H48O3/c1-17(2)18(3)19(4)25(31)28(7)29(32-28)15-12-24-22-9-8-20-16-21(30)10-13-26(20,5)23(22)11-14-27(24,29)6/h8,17-19,21-25,30-31H,9-16H2,1-7H3/t18-,19+,21+,22-,23+,24+,25-,26+,27+,28+,29+/m1/s1
Calculated Properties
ALogP:
6.127 lipophilicity
TPSA:
52.99 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
3
Rotatable Bonds:
4
Ring Count:
5 (0 aromatic)
Chiral Centers:
11
Fsp³:
0.9310 fraction sp³ carbon

Database Information

Compound ID:
SCS-C007544
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Cholestane steroids 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 inhibitory activity NF-κB signaling pathway Compound 3, an intriguing hydroperoxyl sterol, showed considerable NF-κB inhibitory activity, while other molecules were inactive. 10.1002/cbdv.202000214 Chemistry & Biodiversity
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Structure enlarged