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  3. [(1S,5aS,5bR,7aS,11aS,11bR,13aS,13bS)-5b,8,8,11a,13a-pentamethyl-13-oxo-3,5,5a,6,7,7a,9,10,11,11b,12,13b-dodecahydro-1H-phenanthro[1,2-g][2]benzofuran-1-yl] acetate

SCS-C004777

[(1S,5aS,5bR,7aS,11aS,11bR,13aS,13bS)-5b,8,8,11a,13a-pentamethyl-13-oxo-3,5,5a,6,7,7a,9,10,11,11b,12,13b-dodecahydro-1H-phenanthro[1,2-g][2]benzofuran-1-yl] acetate

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

Structure of [(1S,5aS,5bR,7aS,11aS,11bR,13aS,13bS)-5b,8,8,11a,13a-pentamethyl-13-oxo-3,5,5a,6,7,7a,9,10,11,11b,12,13b-dodecahydro-1H-phenanthro[1,2-g][2]benzofuran-1-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

Glossodoris rufomarginata (NA)
Kingdom Metazoa Phylum Mollusca Class Gastropoda Order Nudibranchia Family Chromodorididae Genus Glossodoris Species Glossodoris rufomarginata
South China Sea
DOI: 10.1021/np040002n  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
428.6 Da
Threshold ≤ 500
ALogP
5.70
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C27H40O4
Molecular Weight:
428.6130 Da
SMILES:
CC(=O)O[C@@H]1OCC2=CC[C@H]3[C@]4(C)CC[C@H]5C(C)(C)CCC[C@]5(C)[C@H]4CC(=O)[C@]3(C)[C@H]21
InChIKey:
KFTWUORYIYZBGS-PTOVQJCFSA-N
InChI:
InChI=1S/C27H40O4/c1-16(28)31-23-22-17(15-30-23)8-9-19-26(5)13-10-18-24(2,3)11-7-12-25(18,4)20(26)14-21(29)27(19,22)6/h8,18-20,22-23H,7,9-15H2,1-6H3/t18-,19-,20+,22+,23-,25-,26-,27+/m0/s1
Calculated Properties
ALogP:
5.696 lipophilicity
TPSA:
52.60 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
4
Rotatable Bonds:
1
Ring Count:
5 (0 aromatic)
Chiral Centers:
8
Fsp³:
0.8519 fraction sp³ carbon

Database Information

Compound ID:
SCS-C004777
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 CMNPD: CMNPD14573

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged