SCS-C001256
29-hydroperoxystigmasta-5,24(28)-dien-3-ol
Pathway: Terpenoids
Superclass: Steroids
Class: Stigmastane steroids
Chemical Structure
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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.
Source Information
Xestospongia testudinaria
(sponge)
Original source name: Xestospongia testudinaria Lamarck
Kingdom
Metazoa
Phylum
Porifera
Class
Demospongiae
Order
Haplosclerida
Family
Petrosiidae
Genus
Xestospongia
Species
Xestospongia testudinaria
Sanya
· -8.5m
DOI:
10.3109/13880209.2013.821664
· Pharmaceutical Biology
Drug-likeness (Lipinski Ro5)
Molecular Weight
444.7 Da
Threshold ≤ 500
ALogP
7.41
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C29H48O3
Molecular Weight:
444.7000 Da
SMILES:
CC(C)C(=CCOO)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey:
QQFQTVKOYPPUOZ-MEKCMURWSA-N
InChI:
InChI=1S/C29H48O3/c1-19(2)21(14-17-32-31)7-6-20(3)25-10-11-26-24-9-8-22-18-23(30)12-15-28(22,4)27(24)13-16-29(25,26)5/h8,14,19-20,23-27,30-31H,6-7,9-13,15-18H2,1-5H3/t20-,23?,24+,25-,26+,27+,28+,29-/m1/s1
Calculated Properties
ALogP:
7.415 lipophilicity
TPSA:
49.69 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
3
Rotatable Bonds:
7
Ring Count:
4
(0 aromatic)
Chiral Centers:
8
Fsp³:
0.8621 fraction sp³ carbon
Database Information
Compound ID:
SCS-C001256
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Stigmastane 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 |
|---|---|---|---|---|
| Enzyme inhibition | IC50 | HMGCR-GFP | 3.8 μg/mL | 10.3109/13880209.2013.821664 Pharmaceutical Biology |
| Receptor / Signaling modulation | IC50 | Foxo3a | 4.5 μg/mL | 10.3109/13880209.2013.821664 Pharmaceutical Biology |
| Enzyme inhibition | IC50 | PTP1B | 5.8 μg/mL | 10.3109/13880209.2013.821664 Pharmaceutical Biology |
| Anti-inflammatory | IC50 | NF-kB-luciferase | 12.6 μg/mL | 10.3109/13880209.2013.821664 Pharmaceutical Biology |
| Metabolic / Lipid regulation | IC50 | PGC-1a | 14.2 μg/mL | 10.3109/13880209.2013.821664 Pharmaceutical Biology |
| Enzyme inhibition | IC50 | MMP | 19.1 μg/mL | 10.3109/13880209.2013.821664 Pharmaceutical Biology |