SCS-C004747
(3aS,5R,5aR,8S,8aS)-8-acetyl-5-hydroxy-3a-methoxy-1,5-dimethyl-4,5a,6,7,8,8a-hexahydrocyclopenta[e][1]benzofuran-2-one
Pathway: Terpenoids
Superclass: Sesquiterpenoids
Class: Oplopane sesquiterpenoids
Glycoside
Chemical Structure
![Structure of (3aS,5R,5aR,8S,8aS)-8-acetyl-5-hydroxy-3a-methoxy-1,5-dimethyl-4,5a,6,7,8,8a-hexahydrocyclopenta[e][1]benzofuran-2-one](/scsmarinenp/static/images/structures/SCS-C004747.png)
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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.
Source Information
Echinogorgia pseudosassapo
(NA)
Kingdom
Metazoa
Phylum
Cnidaria
Class
Anthozoa
Order
Malacalcyonacea
Family
Plexauridae
Genus
Echinogorgia
Species
Echinogorgia pseudosassapo
South China Sea
DOI:
10.1021/ol200234r
· Organic Letters
Drug-likeness (Lipinski Ro5)
Molecular Weight
294.3 Da
Threshold ≤ 500
ALogP
1.59
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C16H22O5
Molecular Weight:
294.3470 Da
SMILES:
CO[C@]12C[C@@](C)(O)[C@@H]3CC[C@H](C(C)=O)[C@H]3C1=C(C)C(=O)O2
InChIKey:
NUXHYFPLSZEUAG-BQJFBPGXSA-N
InChI:
InChI=1S/C16H22O5/c1-8-13-12-10(9(2)17)5-6-11(12)15(3,19)7-16(13,20-4)21-14(8)18/h10-12,19H,5-7H2,1-4H3/t10-,11-,12-,15-,16+/m1/s1
Calculated Properties
ALogP:
1.589 lipophilicity
TPSA:
72.83 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
5
Rotatable Bonds:
2
Ring Count:
3
(0 aromatic)
Chiral Centers:
5
Fsp³:
0.7500 fraction sp³ carbon
Database Information
Compound ID:
SCS-C004747
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesquiterpenoids
NPClassifier Class:
Oplopane sesquiterpenoids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.