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SCS-C006704

(24E)-29-hydroperoxystigmasta-4,24(28)-dien-3-one

Pathway: Terpenoids Superclass: Steroids Class: Stigmastane steroids
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Chemical Structure

Structure of (24E)-29-hydroperoxystigmasta-4,24(28)-dien-3-one
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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.
Download: SDF SMILES

Source Information

Xestospongia sp. (sponge)
Kingdom Metazoa Phylum Porifera Class Demospongiae Order Haplosclerida Family Petrosiidae Genus Xestospongia Species NA
Offshore Hainan Island  · 20°13'21" N, 109°55'21" E
DOI: 10.3390/md23010036  · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight
442.7 Da
Threshold ≤ 500
ALogP
7.62
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C29H46O3
Molecular Weight:
442.6840 Da
SMILES:
CC(C)/C(=C/COO)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChIKey:
AMDDLVXGMIVXIP-HCILOOABSA-N
InChI:
InChI=1S/C29H46O3/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/h14,18-20,24-27,31H,6-13,15-17H2,1-5H3/b21-14+/t20-,24+,25-,26+,27+,28+,29-/m1/s1
Calculated Properties
ALogP:
7.623 lipophilicity
TPSA:
46.53 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
7
Ring Count:
4 (0 aromatic)
Chiral Centers:
7
Fsp³:
0.8276 fraction sp³ carbon

Database Information

Compound ID:
SCS-C006704
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Stigmastane steroids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

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
Antitumor cell viability RAW 264.7 cells 76.9 % 10.3390/md23010036 Marine Drugs
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Structure enlarged