SCS-C008208

9-deoxyinsulicolide A

Pathway: Terpenoids Superclass: Sesquiterpenoids Class: Drimane sesquiterpenoids

Chemical Structure

Loading 3D structure...

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

Aspergillus ochraceus (fungus)

Original source name: Aspergillus ochraceus (isolated from marine alga Coelarthrum sp.)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus ochraceus

South China Sea

DOI: 10.1021/acs.jnatprod.7b00698 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

415.4 Da

Threshold ≤ 500

ALogP

3.04

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H25NO7

Molecular Weight:

415.4420 Da

SMILES:

C[C@]1(CO)CCC[C@@]2(C)[C@H]3COC(=O)C3=C[C@H](OC(=O)c3ccc([N+](=O)[O-])cc3)[C@@H]12

InChIKey:

                        HETGKXPYEMRZHE-BDCMKUQMSA-N
                        
                    

InChI:

InChI=1S/C22H25NO7/c1-21(12-24)8-3-9-22(2)16-11-29-20(26)15(16)10-17(18(21)22)30-19(25)13-4-6-14(7-5-13)23(27)28/h4-7,10,16-18,24H,3,8-9,11-12H2,1-2H3/t16-,17-,18-,21+,22-/m0/s1

Calculated Properties

ALogP:

3.038 lipophilicity

TPSA:

115.97 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (1 aromatic)

Chiral Centers:

Fsp³:

0.5455 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008208

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Sesquiterpenoids

NPClassifier Class:

Drimane sesquiterpenoids

Glycoside:

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
Antitumor	IC50	ACHN, OS-RC-2, 786-O renal carcinoma cells	> 100.0 μM	10.1021/acs.jnatprod.7b00698 Journal of Natural Products

Back to Compounds