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SCS-C007021

(24S)-ergosta-5,25-diene-3β,20,24,28-tetrol

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

Structure of (24S)-ergosta-5,25-diene-3β,20,24,28-tetrol
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

Sinularia sp. (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species NA
South China Sea  · 10 m
DOI: 10.1016/j.steroids.2019.108425  · Steroids

Drug-likeness (Lipinski Ro5)

Molecular Weight
446.7 Da
Threshold ≤ 500
ALogP
4.76
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C28H46O4
Molecular Weight:
446.6720 Da
SMILES:
C=C(C)[C@](O)(CO)CC[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C
InChIKey:
CZCNZAJJLQJYQR-CDZSUCCGSA-N
InChI:
InChI=1S/C28H46O4/c1-18(2)28(32,17-29)15-14-27(5,31)24-9-8-22-21-7-6-19-16-20(30)10-12-25(19,3)23(21)11-13-26(22,24)4/h6,20-24,29-32H,1,7-17H2,2-5H3/t20-,21-,22-,23-,24-,25-,26-,27-,28+/m0/s1
Calculated Properties
ALogP:
4.757 lipophilicity
TPSA:
80.92 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
4
Rotatable Bonds:
6
Ring Count:
4 (0 aromatic)
Chiral Centers:
9
Fsp³:
0.8571 fraction sp³ carbon

Database Information

Compound ID:
SCS-C007021
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
Antitumor IC50 H157 cancer cell proliferation 10.38 μM 10.1016/j.steroids.2019.108425 Steroids
Cellular modulation — apoptosis-related proteins Bax — Structured numeric value is not available in this record; see the primary reference. 10.1016/j.steroids.2019.108425 Steroids
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Structure enlarged