SCS-C005888

9α,14-dihydroxy-6β-p-nitrobenzoylcinnamolide

Pathway: Terpenoids Superclass: Sesquiterpenoids Class: Drimane sesquiterpenoids

Chemical Structure

Structure of 9α,14-dihydroxy-6β-p-nitrobenzoylcinnamolide

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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 sp. SCSGAF 0076 (OY10607) (coral-derived fungus)

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

Offshore Hainan Island · 18°11′N, 109°25′E

DOI: 10.1177/1934578x1300800825 · Natural Product Communications

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(CO)CCC[C@@]2(C)[C@H]1[C@H](OC(=O)c1ccc([N+](=O)[O-])cc1)C=C1C(=O)OC[C@@]12O

InChIKey:

                        ISKLVGANHNNXLD-PNBTUHDLSA-N
                        
                    

InChI:

InChI=1S/C22H25NO8/c1-20(11-24)8-3-9-21(2)17(20)16(10-15-19(26)30-12-22(15,21)27)31-18(25)13-4-6-14(7-5-13)23(28)29/h4-7,10,16-17,24,27H,3,8-9,11-12H2,1-2H3/t16-,17+,20-,21+,22-/m1/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-C005888

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
Antiviral	IC50	influenza virus strain H1N1 (A/WSN/33)	7.4 μM	10.1177/1934578x1300800825 Natural Product Communications
Antiviral	IC50	influenza virus strain H3N2 (A/Hong Kong/8/68)	4.3 μM	10.1177/1934578x1300800825 Natural Product Communications

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