SCS-C001255

24-hydroperoxy-24-vinylcholesterol

Pathway: Terpenoids Superclass: Steroids Class: Cholestane steroids

Chemical Structure

Structure of 24-hydroperoxy-24-vinylcholesterol

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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

Xestospongia testudinaria (sponge)

Original source name: Xestospongia testudinaria Lamarck

Kingdom Metazoa Phylum Porifera Class Demospongiae Order Haplosclerida Family Petrosiidae Genus Xestospongia Species Xestospongia testudinaria

Sanya · -8.5m

DOI: 10.3109/13880209.2013.821664 · Pharmaceutical Biology

Drug-likeness (Lipinski Ro5)

Molecular Weight

444.7 Da

Threshold ≤ 500

ALogP

7.41

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:

C29H48O3

Molecular Weight:

444.7000 Da

SMILES:

C=CC(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)(OO)C(C)C

InChIKey:

                        WLNWTSOEOWZEGI-SVSQYMGHSA-N
                        
                    

InChI:

InChI=1S/C29H48O3/c1-7-29(32-31,19(2)3)17-12-20(4)24-10-11-25-23-9-8-21-18-22(30)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-8,19-20,22-26,30-31H,1,9-18H2,2-6H3/t20-,22+,23+,24-,25+,26+,27+,28-,29?/m1/s1

Calculated Properties

ALogP:

7.413 lipophilicity

TPSA:

49.69 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.8621 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001255

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Steroids

NPClassifier Class:

Cholestane steroids

Glycoside:

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-kB-luciferase	31.3 μg/mL	10.3109/13880209.2013.821664 Pharmaceutical Biology

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