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  3. [(1S,4S,5bR,11aS,13R,13aS,13bR)-1-acetyloxy-13-hydroxy-5b,8,8,11a,13a-pentamethyl-1,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[2,1-e][2]benzofuran-4-yl] acetate

SCS-C005917

[(1S,4S,5bR,11aS,13R,13aS,13bR)-1-acetyloxy-13-hydroxy-5b,8,8,11a,13a-pentamethyl-1,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[2,1-e][2]benzofuran-4-yl] acetate

Pathway: Terpenoids Superclass: Sesterterpenoids Class: Scalarane sesterterpenoids Glycoside
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Chemical Structure

Structure of [(1S,4S,5bR,11aS,13R,13aS,13bR)-1-acetyloxy-13-hydroxy-5b,8,8,11a,13a-pentamethyl-1,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[2,1-e][2]benzofuran-4-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

Hyrtios sp. (NA)
Kingdom Metazoa Phylum Porifera Class Demospongiae Order Dictyoceratida Family Thorectidae Genus Hyrtios Species NA
South China Sea
DOI: 10.1177/1934578x1400900608  · Natural Product Communications

Drug-likeness (Lipinski Ro5)

Molecular Weight
488.7 Da
Threshold ≤ 500
ALogP
5.38
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C29H44O6
Molecular Weight:
488.6650 Da
SMILES:
CC(=O)O[C@@H]1OC=C2[C@@H](OC(C)=O)CC3[C@]4(C)CCC5C(C)(C)CCC[C@]5(C)C4C[C@@H](O)[C@]3(C)[C@H]21
InChIKey:
VYIQDOVNWPEWRJ-ZSRNYRKMSA-N
InChI:
InChI=1S/C29H44O6/c1-16(30)34-19-13-22-28(6)12-9-20-26(3,4)10-8-11-27(20,5)21(28)14-23(32)29(22,7)24-18(19)15-33-25(24)35-17(2)31/h15,19-25,32H,8-14H2,1-7H3/t19-,20?,21?,22?,23+,24+,25-,27-,28+,29+/m0/s1
Calculated Properties
ALogP:
5.377 lipophilicity
TPSA:
82.06 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
6
Rotatable Bonds:
2
Ring Count:
5 (0 aromatic)
Chiral Centers:
10
Fsp³:
0.8621 fraction sp³ carbon

Database Information

Compound ID:
SCS-C005917
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesterterpenoids
NPClassifier Class:
Scalarane sesterterpenoids
Glycoside:
Yes
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 human cancer cell line HCT-116 1.5 μg/mL 10.1177/1934578x1400900608 Natural Product Communications
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Structure enlarged