SCS-C004417
methyl (1S,4R,7S,8aR)-8a-methyl-4-[(2E,4Z)-8-methyldeca-2,4-dienoyl]oxy-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylate
Pathway: Terpenoids
Superclass: Sesquiterpenoids
Chemical Structure
![Structure of methyl (1S,4R,7S,8aR)-8a-methyl-4-[(2E,4Z)-8-methyldeca-2,4-dienoyl]oxy-6-oxo-7-(3-oxoprop-1-en-2-yl)-1,2,3,4,7,8-hexahydronaphthalene-1-carboxylate](/scsmarinenp/static/images/structures/SCS-C004417.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
Xylaria sp.
(gorgonian-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Xylariales
Family
Xylariaceae
Genus
Xylaria
Species
NA
South China Sea
DOI:
10.1039/c3np70117d
· Natural Product Reports
Drug-likeness (Lipinski Ro5)
Molecular Weight
456.6 Da
Threshold ≤ 500
ALogP
4.70
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C27H36O6
Molecular Weight:
456.5790 Da
SMILES:
C=C(C=O)[C@@H]1C[C@@]2(C)C(=CC1=O)[C@H](OC(=O)/C=C/C=C\CCC(C)CC)CC[C@@H]2C(=O)OC
InChIKey:
VGRLZLRYWXXGNZ-QXDQPYDQSA-N
InChI:
InChI=1S/C27H36O6/c1-6-18(2)11-9-7-8-10-12-25(30)33-24-14-13-21(26(31)32-5)27(4)16-20(19(3)17-28)23(29)15-22(24)27/h7-8,10,12,15,17-18,20-21,24H,3,6,9,11,13-14,16H2,1-2,4-5H3/b8-7-,12-10+/t18?,20-,21+,24+,27+/m0/s1
Calculated Properties
ALogP:
4.697 lipophilicity
TPSA:
86.74 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
6
Rotatable Bonds:
10
Ring Count:
2
(0 aromatic)
Chiral Centers:
5
Fsp³:
0.5556 fraction sp³ carbon
Database Information
Compound ID:
SCS-C004417
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesquiterpenoids
NPClassifier Class:
N/A
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.