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  3. (5bR,11aS,13R,13aS)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-4,5,5a,6,7,7a,9,10,11,11b,12,13-dodecahydro-3H-phenanthro[1,2-g][2]benzofuran-1-one

SCS-C005920

(5bR,11aS,13R,13aS)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-4,5,5a,6,7,7a,9,10,11,11b,12,13-dodecahydro-3H-phenanthro[1,2-g][2]benzofuran-1-one

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

Structure of (5bR,11aS,13R,13aS)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-4,5,5a,6,7,7a,9,10,11,11b,12,13-dodecahydro-3H-phenanthro[1,2-g][2]benzofuran-1-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
5.27
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)C3=C(CCC12)COC3=O
InChIKey:
FMYCKOLKWHMLJO-DWDIBINLSA-N
InChI:
InChI=1S/C25H38O3/c1-22(2)10-6-11-23(3)16(22)9-12-24(4)17-8-7-15-14-28-21(27)20(15)25(17,5)19(26)13-18(23)24/h16-19,26H,6-14H2,1-5H3/t16?,17?,18?,19-,23+,24+,25-/m1/s1
Calculated Properties
ALogP:
5.270 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:
7
Fsp³:
0.8800 fraction sp³ carbon

Database Information

Compound ID:
SCS-C005920
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 12.1 μg/mL 10.1177/1934578x1400900608 Natural Product Communications
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Structure enlarged