SCS-C002215
5α,8α-epidioxy-cholest-6-en-3β-ol
Pathway: Terpenoids
Superclass: Steroids
Class: Cholestane steroids
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Menella kanisa
(gorgonian coral)
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Malacalcyonacea
Family
Plexauridae
Genus
Menella
Species
Menella kanisa
Beihai
· -10m
DOI:
10.3724/sp.j.1008.2013.00819
· Academic Journal of Second Military Medical University
Spongia officinalis
(Spongia officinalis var. ceylonica)
Kingdom
Metazoa
Phylum
Porifera
Class
Demospongiae
Order
Dictyoceratida
Family
Spongiidae
Genus
Spongia
Species
Spongia officinalis
South China Sea
· shallow water
DOI:
10.1002/cbdv.202400519
· Chemistry & Biodiversity
Drug-likeness (Lipinski Ro5)
Molecular Weight
416.6 Da
Threshold ≤ 500
ALogP
6.45
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C27H44O3
Molecular Weight:
416.6400 Da
SMILES:
CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@]23C=C[C@]2(C[C@@H](O)CC[C@]12C)OO3
InChIKey:
FOISYVRNZSWLHL-MEKQHADNSA-N
InChI:
InChI=1S/C27H44O3/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/h15-16,18-23,28H,6-14,17H2,1-5H3/t19-,20+,21-,22-,23-,24-,25-,26-,27+/m1/s1
Calculated Properties
ALogP:
6.452 lipophilicity
TPSA:
38.69 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
5
Ring Count:
6
(0 aromatic)
Chiral Centers:
9
Fsp³:
0.9259 fraction sp³ carbon
Database Information
Compound ID:
SCS-C002215
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Cholestane steroids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
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 | — | cited from ref.[21] | Inhibitory activity against human breast cancer cell line MCF-7 (cited from ref.[22]); antimicrobial activity against Bacillus megaterium, E. coli, Septoria tritici, Ustilago violacea, and Chlorella vulgaris (cited from ref.[21]) | 10.3724/sp.j.1008.2013.00819 Academic Journal of Second Military Medical University |
| Anti-inflammatory | NO production level | LPS-induced NO production | 49.4 % | 10.1002/cbdv.202400519 Chemistry & Biodiversity |
| Antitumor | IC50 | HEL cells | 5.16–7.68 μM | 10.1002/cbdv.202400519 Chemistry & Biodiversity |
| Anti-inflammatory | gene expression modulation | IL-1β, IL-6, HO-1, NQO1 mRNA levels | — Structured numeric value is not available in this record; see the primary reference. | 10.1002/cbdv.202400519 Chemistry & Biodiversity |