SCS-C005673
(1R,3R,5R,6S,10R)-5-ethenyl-3,9,10-trihydroxy-6-methoxy-5,11,11-trimethyl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadec-2(7)-en-8-one
Pathway: Terpenoids
Superclass: Diterpenoids
Class: Pimarane and Isopimarane diterpenoids
Glycoside
Chemical Structure
![Structure of (1R,3R,5R,6S,10R)-5-ethenyl-3,9,10-trihydroxy-6-methoxy-5,11,11-trimethyl-16-oxatetracyclo[7.5.2.01,10.02,7]hexadec-2(7)-en-8-one](/scsmarinenp/static/images/structures/SCS-C005673.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
Epicoccum sp.
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Dothideomycetes
Order
Pleosporales
Family
Didymellaceae
Genus
Epicoccum
Species
NA
Guangzhou
DOI:
10.1039/c6np00124f
· Natural Product Reports
Drug-likeness (Lipinski Ro5)
Molecular Weight
378.5 Da
Threshold ≤ 500
ALogP
1.48
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C21H30O6
Molecular Weight:
378.4650 Da
SMILES:
C=C[C@@]1(C)C[C@@H](O)C2=C(C(=O)[C@@]3(O)OC[C@@]24CCCC(C)(C)[C@@]43O)[C@H]1OC
InChIKey:
VCNLMXIMSMCNMZ-DFILUXEFSA-N
InChI:
InChI=1S/C21H30O6/c1-6-18(4)10-12(22)14-13(16(18)26-5)15(23)20(24)21(25)17(2,3)8-7-9-19(14,21)11-27-20/h6,12,16,22,24-25H,1,7-11H2,2-5H3/t12-,16-,18+,19+,20-,21-/m1/s1
Calculated Properties
ALogP:
1.484 lipophilicity
TPSA:
96.22 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
6
Rotatable Bonds:
2
Ring Count:
4
(0 aromatic)
Chiral Centers:
6
Fsp³:
0.7619 fraction sp³ carbon
Database Information
Compound ID:
SCS-C005673
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Diterpenoids
NPClassifier Class:
Pimarane and Isopimarane diterpenoids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.