SCS-C002218
5α,8α-epidioxy-24-methyl-cholesta-6,24(28)-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
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
Sinularia depressa
(soft coral)
Original source name: Sinularia depressa Tixier-Durivault
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Malacalcyonacea
Family
Sinulariidae
Genus
Sinularia
Species
Sinularia depressa
South China Sea
DOI:
10.1016/j.bmcl.2012.12.087
· Bioorganic & Medicinal Chemistry Letters
Drug-likeness (Lipinski Ro5)
Molecular Weight
428.6 Da
Threshold ≤ 500
ALogP
6.62
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:
C=C(CC[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)C(C)C
InChIKey:
XGUKSASAYIQRBB-WBIZBJRUSA-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/h15-16,18,20-24,29H,3,7-14,17H2,1-2,4-6H3/t20-,21+,22-,23-,24-,25-,26-,27-,28+/m1/s1
Calculated Properties
ALogP:
6.618 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:
0.8571 fraction sp³ carbon
Database Information
Compound ID:
SCS-C002218
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 | — | MCF-7 | Inhibitory activity against human breast cancer cell line MCF-7 (cited from ref.[22]) | 10.3724/sp.j.1008.2013.00819 Academic Journal of Second Military Medical University |
| Antibacterial | — | Staphylococcus aureus Newman strain | steroids 7, 11, and 15 exhibited a different level of antibacterial activity against Staphylococcus aureus Newman strain | 10.1016/j.bmcl.2012.12.087 Bioorganic & Medicinal Chemistry Letters |