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  3. [(1S,3R,7R,8S,9S,10R,13R,14S,17R)-1,3-dihydroxy-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-7-yl] acetate

SCS-C007022

[(1S,3R,7R,8S,9S,10R,13R,14S,17R)-1,3-dihydroxy-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-7-yl] acetate

Pathway: Terpenoids Superclass: Steroids Class: Cholestane steroids | Ergostane steroids
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Chemical Structure

Structure of [(1S,3R,7R,8S,9S,10R,13R,14S,17R)-1,3-dihydroxy-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-7-yl] acetate
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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

Sinularia sp. (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species NA
South China Sea  · 10 m
DOI: 10.1016/j.steroids.2019.108425  · Steroids

Drug-likeness (Lipinski Ro5)

Molecular Weight
472.7 Da
Threshold ≤ 500
ALogP
6.07
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C30H48O4
Molecular Weight:
472.7100 Da
SMILES:
C=C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@@H](OC(C)=O)C=C4C[C@@H](O)C[C@H](O)[C@]4(C)[C@H]3CC[C@]12C)C(C)C
InChIKey:
YFUNBZXZDHMRBJ-DQTBKWPISA-N
InChI:
InChI=1S/C30H48O4/c1-17(2)18(3)8-9-19(4)23-10-11-24-28-25(12-13-29(23,24)6)30(7)21(14-22(32)16-27(30)33)15-26(28)34-20(5)31/h15,17,19,22-28,32-33H,3,8-14,16H2,1-2,4-7H3/t19-,22-,23-,24+,25+,26+,27+,28+,29-,30+/m1/s1
Calculated Properties
ALogP:
6.067 lipophilicity
TPSA:
66.76 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
4
Rotatable Bonds:
6
Ring Count:
4 (0 aromatic)
Chiral Centers:
10
Fsp³:
0.8333 fraction sp³ carbon

Database Information

Compound ID:
SCS-C007022
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Cholestane steroids Ergostane 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
Antitumor IC50 cancer cell proliferation 10.14–41.71 μM 10.1016/j.steroids.2019.108425 Steroids
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Structure enlarged