SCS-C006703
(3β,5α,6β)-5,6-epoxy-3β-hydroxycholestan-7-one
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
Lobophytum sp.
(soft coral)
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Malacalcyonacea
Family
Alcyoniidae
Genus
Lobophytum
Species
NA
Offshore Hainan Island
· 18°14'00" N, 109°22'11" E
DOI:
10.3390/md23010036
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
416.6 Da
Threshold ≤ 500
ALogP
5.78
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:
416.6460 Da
SMILES:
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C(=O)[C@@H]4O[C@@]45C[C@@H](O)CC[C@]5(C)[C@H]3CC[C@]12C
InChIKey:
HUTIPXVCGHWMMK-SXYRFLAXSA-N
InChI:
InChI=1S/C27H44O3/c1-16(2)7-6-8-17(3)19-9-10-20-22-21(12-13-25(19,20)4)26(5)14-11-18(28)15-27(26)24(30-27)23(22)29/h16-22,24,28H,6-15H2,1-5H3/t17-,18+,19-,20+,21+,22+,24+,25-,26-,27+/m1/s1
Calculated Properties
ALogP:
5.779 lipophilicity
TPSA:
49.83 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
5
Ring Count:
5
(0 aromatic)
Chiral Centers:
10
Fsp³:
0.9630 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006703
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 | MIC | vancomycin-resistant Enterococcus faecium G1 | 100.0 μM | 10.3390/md23010036 Marine Drugs |
| Antibacterial | MIC | Streptococcus parauberis KSP28 | 100.0 μM | 10.3390/md23010036 Marine Drugs |
| Antibacterial | MIC | Photobacterium damselae FP2244 | 100.0 μM | 10.3390/md23010036 Marine Drugs |
| Antibacterial | MIC | Pseudomonas aeruginosa ZJ028 | 100.0 μM | 10.3390/md23010036 Marine Drugs |
| Anti-inflammatory | IC50 | LPS-induced NO production | 13.48 μM | 10.3390/md23010036 Marine Drugs |