SCS-C001257

5α,8α-epidioxycholest-6-en-3β-ol

Pathway: Terpenoids Superclass: Steroids Class: Cholestane steroids

Chemical Structure

Structure of 5α,8α-epidioxycholest-6-en-3β-ol

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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

Mycale sp. (sponge)

Kingdom Metazoa Phylum Porifera Class Demospongiae Order Poecilosclerida Family Mycalidae Genus Mycale Species NA

Sanya · -8.5m

DOI: 10.3109/13880209.2013.821664 · Pharmaceutical Biology

Drug-likeness (Lipinski Ro5)

Molecular Weight

414.6 Da

Threshold ≤ 500

ALogP

6.23

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:

C27H42O3

Molecular Weight:

414.6300 Da

SMILES:

CC(C)C/C=C/[C@@H](C)C1CCC2[C@]1(C)CCC1[C@]23C=C[C@]2(C[C@@H](O)CC[C@]12C)OO3

InChIKey:

                        WISOACODKWCRQK-ADKHVQPASA-N
                        
                    

InChI:

InChI=1S/C27H42O3/c1-18(2)7-6-8-19(3)21-9-10-22-24(21,4)13-12-23-25(5)14-11-20(28)17-26(25)15-16-27(22,23)30-29-26/h6,8,15-16,18-23,28H,7,9-14,17H2,1-5H3/b8-6+/t19-,20+,21?,22?,23?,24-,25-,26-,27+/m1/s1

Calculated Properties

ALogP:

6.228 lipophilicity

TPSA:

38.69 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (0 aromatic)

Chiral Centers:

Fsp³:

0.8519 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001257

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
Enzyme inhibition	IC50	HMGCR-GFP	4.9 μg/mL	10.3109/13880209.2013.821664 Pharmaceutical Biology
Anti-inflammatory	IC50	NF-kB-luciferase	16.3 μg/mL	10.3109/13880209.2013.821664 Pharmaceutical Biology
Receptor / Signaling modulation	IC50	Foxo3a	32.8 μg/mL	10.3109/13880209.2013.821664 Pharmaceutical Biology

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