SCS-C007479

fennebricin D

Pathway: Alkaloids Superclass: Tyrosine alkaloids Class: Tetrahydroisoquinoline alkaloids

Chemical Structure

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Download: SDF SMILES

Source Information

Xestospongia sp. (sponge)

Kingdom Metazoa Phylum Porifera Class Demospongiae Order Haplosclerida Family Petrosiidae Genus Xestospongia Species NA

South China Sea · 10 m

DOI: 10.4155/fmc.15.169 · Future Medicinal Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

650.7 Da

Threshold ≤ 500

ALogP

2.13

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

2 violations (MW, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C35H42N2O10

Molecular Weight:

650.7250 Da

SMILES:

C/C=C(/C)C(=O)OC[C@H]1C2=C(C[C@H]3[C@H]4C5=C(C(=O)C(C)=C(OC)C5=O)[C@H](OCC)[C@@H]([C@H](CC(C)=O)N13)N4C)C(=O)C(C)=C(OC)C2=O

InChIKey:

                        OLLBAXAKBWEJLN-PREFKONUSA-N
                        
                    

InChI:

InChI=1S/C35H42N2O10/c1-10-15(3)35(43)47-14-22-23-19(28(39)17(5)32(44-8)30(23)41)13-21-26-24-25(29(40)18(6)33(45-9)31(24)42)34(46-11-2)27(36(26)7)20(37(21)22)12-16(4)38/h10,20-22,26-27,34H,11-14H2,1-9H3/b15-10-/t20-,21-,22-,26-,27+,34-/m0/s1

Calculated Properties

ALogP:

2.125 lipophilicity

TPSA:

145.82 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (0 aromatic)

Chiral Centers:

Fsp³:

0.5429 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007479

NPClassifier Pathway:

Alkaloids

NPClassifier Superclass:

Tyrosine alkaloids

NPClassifier Class:

Tetrahydroisoquinoline alkaloids

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
Anti-inflammatory	IC50	NF-κB signaling pathway	5.7 μM	10.4155/fmc.15.169 Future Medicinal Chemistry
Antitumor	IC50	A549 and HL-60 tumor cell lines	> 100.0 μM	10.4155/fmc.15.169 Future Medicinal Chemistry

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