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  3. (1R,2E,6E,9S,10E,14R)-9-hydroxy-3,7,11,15,15-pentamethylbicyclo[12.1.0]pentadeca-2,6,10-trien-4-one

SCS-C003192

(1R,2E,6E,9S,10E,14R)-9-hydroxy-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,9S,10E,14R)-9-hydroxy-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  · -20 meters
DOI: 10.1002/chem.202300055  · Chemistry – A European Journal

Drug-likeness (Lipinski Ro5)

Molecular Weight
302.5 Da
Threshold ≤ 500
ALogP
4.60
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C20H30O2
Molecular Weight:
302.4580 Da
SMILES:
C/C1=C\[C@@H](O)C/C(C)=C/CC(=O)/C(C)=C/[C@@H]2[C@@H](CC1)C2(C)C
InChIKey:
OQTLYSXEGAWSHV-SATRCACTSA-N
InChI:
InChI=1S/C20H30O2/c1-13-6-8-17-18(20(17,4)5)12-15(3)19(22)9-7-14(2)11-16(21)10-13/h7,10,12,16-18,21H,6,8-9,11H2,1-5H3/b13-10+,14-7+,15-12+/t16-,17-,18-/m1/s1
Calculated Properties
ALogP:
4.601 lipophilicity
TPSA:
37.30 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
2
Rotatable Bonds:
0
Ring Count:
2 (0 aromatic)
Chiral Centers:
3
Fsp³:
0.6500 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003192
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: CMNPD20371

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged