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  3. (5S,5aS,8aS)-5-hydroxy-1,5-dimethyl-8-methylidene-6,7,8a,9-tetrahydro-5aH-azuleno[6,5-b]furan-2-one

SCS-C000135

(5S,5aS,8aS)-5-hydroxy-1,5-dimethyl-8-methylidene-6,7,8a,9-tetrahydro-5aH-azuleno[6,5-b]furan-2-one

Pathway: Terpenoids Superclass: Sesquiterpenoids Class: Cadinane sesquiterpenoids | Guaiane sesquiterpenoids
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Chemical Structure

Structure of (5S,5aS,8aS)-5-hydroxy-1,5-dimethyl-8-methylidene-6,7,8a,9-tetrahydro-5aH-azuleno[6,5-b]furan-2-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

Echinogorgia flora (gorgonian coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Plexauridae Genus Echinogorgia Species Echinogorgia flora
Weizhou Island
DOI: 10.1039/d1ra08631f  · RSC Advances

Drug-likeness (Lipinski Ro5)

Molecular Weight
246.3 Da
Threshold ≤ 500
ALogP
2.48
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C15H18O3
Molecular Weight:
246.3060 Da
SMILES:
C=C1CC[C@H]2[C@@H]1CC1=C(C)C(=O)OC1=C[C@@]2(C)O
InChIKey:
JMOYGQYPTBDGQO-IFUGULHKSA-N
InChI:
InChI=1S/C15H18O3/c1-8-4-5-12-10(8)6-11-9(2)14(16)18-13(11)7-15(12,3)17/h7,10,12,17H,1,4-6H2,2-3H3/t10-,12+,15-/m1/s1
Calculated Properties
ALogP:
2.481 lipophilicity
TPSA:
46.53 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
0
Ring Count:
3 (0 aromatic)
Chiral Centers:
3
Fsp³:
0.5333 fraction sp³ carbon

Database Information

Compound ID:
SCS-C000135
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesquiterpenoids
NPClassifier Class:
Cadinane sesquiterpenoids Guaiane sesquiterpenoids
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
Neuroprotective / Neuromodulatory — Macrophage infiltration around neuromasts in zebrafish — Structured numeric value is not available in this record; see the primary reference. 10.1039/d1ra08631f RSC Advances
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Structure enlarged