SCS-C008207

6β,9α-dihydroxy-14-p-nitrobenzoyl-cinnamolide

Pathway: Terpenoids Superclass: Sesquiterpenoids Class: Drimane sesquiterpenoids

Chemical Structure

Structure of 6β,9α-dihydroxy-14-p-nitrobenzoyl-cinnamolide

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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

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

431.4 Da

Threshold ≤ 500

ALogP

2.15

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H25NO8

Molecular Weight:

431.4410 Da

SMILES:

C[C@]1(COC(=O)c2ccc([N+](=O)[O-])cc2)CCC[C@@]2(C)[C@H]1[C@@H](O)C=C1C(=O)OC[C@@]12O

InChIKey:

                        SXOSXJVAEAFKDC-RGBOINFLSA-N
                        
                    

InChI:

InChI=1S/C22H25NO8/c1-20(11-30-18(25)13-4-6-14(7-5-13)23(28)29)8-3-9-21(2)17(20)16(24)10-15-19(26)31-12-22(15,21)27/h4-7,10,16-17,24,27H,3,8-9,11-12H2,1-2H3/t16-,17-,20+,21-,22+/m0/s1

Calculated Properties

ALogP:

2.153 lipophilicity

TPSA:

136.20 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-C008207

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	786-O renal carcinoma cells	4.3 μM	10.1021/acs.jnatprod.7b00698 Journal of Natural Products
Antitumor	IC50	OS-RC-2 renal carcinoma cells	8.2 μM	10.1021/acs.jnatprod.7b00698 Journal of Natural Products
Antitumor	IC50	ACHN renal carcinoma cells	11.0 μM	10.1021/acs.jnatprod.7b00698 Journal of Natural Products

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