SCS-C002217
(22E,24R)-5α,8α-epidioxy-24-methyl-cholesta-6,22-dien-3β-ol
Pathway: Terpenoids
Superclass: Steroids
Class: Cholestane steroids | Ergostane 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
Acremonium sp. (associated with Ciocalypta sp. sponge) NBUF 150
(NA)
Original source name: Acremonium sp. NBUF150 (isolated from Ciocalypta sp. sponge)
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Hypocreales
Family
Bionectriaceae
Genus
Acremonium
Species
Acremonium sp. NBUF150
South China Sea
· 70 m
DOI:
10.1002/cbdv.202200028
· Chemistry & Biodiversity
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
Drug-likeness (Lipinski Ro5)
Molecular Weight
428.6 Da
Threshold ≤ 500
ALogP
6.47
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C28H44O3
Molecular Weight:
428.6500 Da
SMILES:
CC(C)[C@@H](C)/C=C/[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:
VXOZCESVZIRHCJ-KGHQQZOUSA-N
InChI:
InChI=1S/C28H44O3/c1-18(2)19(3)7-8-20(4)22-9-10-23-25(22,5)13-12-24-26(6)14-11-21(29)17-27(26)15-16-28(23,24)31-30-27/h7-8,15-16,18-24,29H,9-14,17H2,1-6H3/b8-7+/t19-,20+,21-,22+,23+,24+,25+,26+,27+,28-/m0/s1
Calculated Properties
ALogP:
6.474 lipophilicity
TPSA:
38.69 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
4
Ring Count:
6
(0 aromatic)
Chiral Centers:
10
Fsp³:
0.8571 fraction sp³ carbon
Database Information
Compound ID:
SCS-C002217
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Cholestane steroids
Ergostane 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 |
|---|---|---|---|---|
| Antitumor | — | cited from ref.[21] | Inhibitory activity against human breast cancer cell line MCF-7 (cited from ref.[22]); inhibitory activity against human cancer cell lines A549, H460, HGC27 (cited from ref.[25]); 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 |
| Antibacterial | MIC | Vibrio shilonii | 8.0 μg/mL | 10.1002/cbdv.202200028 Chemistry & Biodiversity |
| Antibacterial | MIC | Vibrio brasiliensis | 32.0 μg/mL | 10.1002/cbdv.202200028 Chemistry & Biodiversity |