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SCS-C007543

(22R,23S)-5-hydroperoxy-23-methyl-5α-17,20-epoxyergost-6-ene-3β,22-diol

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

Structure of (22R,23S)-5-hydroperoxy-23-methyl-5α-17,20-epoxyergost-6-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
476.7 Da
Threshold ≤ 500
ALogP
5.59
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C29H48O5
Molecular Weight:
476.6980 Da
SMILES:
CC(C)[C@@H](C)[C@H](C)[C@@H](O)[C@]1(C)O[C@]12CC[C@H]1[C@@H]3C=C[C@@]4(OO)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]12C
InChIKey:
NFZGOIMEMLBZTB-NQFRTGNTSA-N
InChI:
InChI=1S/C29H48O5/c1-17(2)18(3)19(4)24(31)27(7)29(33-27)15-11-23-21-9-14-28(34-32)16-20(30)8-12-25(28,5)22(21)10-13-26(23,29)6/h9,14,17-24,30-32H,8,10-13,15-16H2,1-7H3/t18-,19+,20+,21-,22+,23+,24-,25-,26+,27+,28-,29+/m1/s1
Calculated Properties
ALogP:
5.595 lipophilicity
TPSA:
82.45 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
5
Rotatable Bonds:
5
Ring Count:
5 (0 aromatic)
Chiral Centers:
12
Fsp³:
0.9310 fraction sp³ carbon

Database Information

Compound ID:
SCS-C007543
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 IC50 NF-κB signaling pathway 8.96 μg/mL 10.1002/cbdv.202000214 Chemistry & Biodiversity
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Structure enlarged