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  3. (5bR,11aS,13R,13aS,13bR)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e][2]benzofuran-3-one

SCS-C005918

(5bR,11aS,13R,13aS,13bR)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-1H-phenanthro[2,1-e][2]benzofuran-3-one

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

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

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
386.6 Da
Threshold ≤ 500
ALogP
5.13
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C25H38O3
Molecular Weight:
386.5760 Da
SMILES:
CC1(C)CCC[C@@]2(C)C1CC[C@]1(C)C2C[C@@H](O)[C@@]2(C)C1CC=C1C(=O)OC[C@@H]12
InChIKey:
XJAQPGLKAWWKLX-CSXJVWKVSA-N
InChI:
InChI=1S/C25H38O3/c1-22(2)10-6-11-23(3)17(22)9-12-24(4)18-8-7-15-16(14-28-21(15)27)25(18,5)20(26)13-19(23)24/h7,16-20,26H,6,8-14H2,1-5H3/t16-,17?,18?,19?,20+,23-,24-,25+/m0/s1
Calculated Properties
ALogP:
5.125 lipophilicity
TPSA:
46.53 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
0
Ring Count:
5 (0 aromatic)
Chiral Centers:
8
Fsp³:
0.8800 fraction sp³ carbon

Database Information

Compound ID:
SCS-C005918
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesterterpenoids
NPClassifier Class:
Scalarane sesterterpenoids
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 human cancer cell line HCT-116 13.3 μg/mL 10.1177/1934578x1400900608 Natural Product Communications
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Structure enlarged