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SCS-C007560

(22E,24R)-3β-hydroxy-5,9-epoxyergosta-7,22-dien-6-one

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

Structure of (22E,24R)-3β-hydroxy-5,9-epoxyergosta-7,22-dien-6-one
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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

Acremonium sp. (associated with Ciocalypta sp. sponge) NBUF 150 (NA)
Original source name: Acremonium sp. NBUF150 (isolated from Ciocalypta sp. sponge)
Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Hypocreales Family Bionectriaceae Genus Acremonium Species Acremonium sp. NBUF150
South China Sea  · 70 m
DOI: 10.1002/cbdv.202200028  · Chemistry & Biodiversity

Drug-likeness (Lipinski Ro5)

Molecular Weight
426.6 Da
Threshold ≤ 500
ALogP
5.87
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C28H42O3
Molecular Weight:
426.6410 Da
SMILES:
CC(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=CC(=O)[C@@]45C[C@@H](O)CC[C@]4(C)[C@]3(CC[C@]12C)O5
InChIKey:
XUKWMWQUTQCCDT-IHEPTZRRSA-N
InChI:
InChI=1S/C28H42O3/c1-17(2)18(3)7-8-19(4)21-9-10-22-23-15-24(30)28-16-20(29)11-12-26(28,6)27(23,31-28)14-13-25(21,22)5/h7-8,15,17-22,29H,9-14,16H2,1-6H3/b8-7+/t18-,19+,20-,21+,22-,25+,26+,27+,28-/m0/s1
Calculated Properties
ALogP:
5.865 lipophilicity
TPSA:
46.53 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
4
Ring Count:
6 (0 aromatic)
Chiral Centers:
9
Fsp³:
0.8214 fraction sp³ carbon

Database Information

Compound ID:
SCS-C007560
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
Antibacterial MIC Vibrio brasiliensis 16.0 μg/mL 10.1002/cbdv.202200028 Chemistry & Biodiversity
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Structure enlarged