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  3. (1R,2E,6E,10E,14R)-3,7,11,15,15-pentamethylbicyclo[12.1.0]pentadeca-2,6,10-trien-4-one

SCS-C003031

(1R,2E,6E,10E,14R)-3,7,11,15,15-pentamethylbicyclo[12.1.0]pentadeca-2,6,10-trien-4-one

Pathway: Terpenoids Superclass: Diterpenoids Class: Casbane diterpenoids
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Chemical Structure

Structure of (1R,2E,6E,10E,14R)-3,7,11,15,15-pentamethylbicyclo[12.1.0]pentadeca-2,6,10-trien-4-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

Sinularia depressa (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species Sinularia depressa
Hainan Island
DOI: 10.1021/np900484k  · Journal of Natural Products
Sinularia nanolobata (soft coral)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Sinulariidae Genus Sinularia Species Sinularia nanolobata
South China Sea
DOI: 10.1021/acs.orglett.1c02772  · Organic Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight
286.5 Da
Threshold ≤ 500
ALogP
5.63
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
1
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:
C20H30O
Molecular Weight:
286.4590 Da
SMILES:
C/C1=C\CC(=O)/C(C)=C/[C@@H]2[C@@H](CC/C(C)=C/CC1)C2(C)C
InChIKey:
UJRRNBNNVPPTBX-DTXVRSRVSA-N
InChI:
InChI=1S/C20H30O/c1-14-7-6-8-15(2)10-12-19(21)16(3)13-18-17(11-9-14)20(18,4)5/h7,10,13,17-18H,6,8-9,11-12H2,1-5H3/b14-7+,15-10+,16-13+/t17-,18-/m1/s1
Calculated Properties
ALogP:
5.631 lipophilicity
TPSA:
17.07 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
1
Rotatable Bonds:
0
Ring Count:
2 (0 aromatic)
Chiral Centers:
2
Fsp³:
0.6500 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003031
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Casbane diterpenoids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD20369

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
Anti-inflammatory NO production inhibition NO production compounds 1, 2a, 3, 3a, 4, 5, 7, and 8 at 20 μM displayed inhibitory activity on NO production against LPS-induced inflammation-related BV-2 microglial cells 10.1021/acs.orglett.1c02772 Organic Letters
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Structure enlarged