SCS-C007434

brefeldindole H

Pathway: Alkaloids | Amino acids and Peptides Superclass: Peptide alkaloids Class: Indole diketopiperazine alkaloids (L-Trp, L-Pro)

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Chemical Structure

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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

Penicillium brefeldianum GXIMD 02511 (NA)

Original source name: Penicillium brefeldianum | Penicillium brefeldianum GXIMD 02511

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species Penicillium brefeldianum

South China Sea

DOI: 10.1021/acs.jnatprod.5c00425 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

425.5 Da

Threshold ≤ 500

ALogP

2.65

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C23H27N3O5

Molecular Weight:

425.4850 Da

SMILES:

COc1ccc2c3c([nH]c2c1)[C@@H]1CC(C)(C)O[C@]2(C(=O)N4CCC[C@H]4C(=O)N12)[C@H]3OC

InChIKey:

                        JRGFJJBTYRDLDB-YZQOHXRLSA-N
                        
                    

InChI:

InChI=1S/C23H27N3O5/c1-22(2)11-16-18-17(13-8-7-12(29-3)10-14(13)24-18)19(30-4)23(31-22)21(28)25-9-5-6-15(25)20(27)26(16)23/h7-8,10,15-16,19,24H,5-6,9,11H2,1-4H3/t15-,16-,19-,23-/m0/s1

Calculated Properties

ALogP:

2.647 lipophilicity

TPSA:

84.10 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.5652 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007434

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

Indole diketopiperazine alkaloids (L-Trp, L-Pro)

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	inhibitory	NF-κB	Compounds 1, 2, 4?9, 11?13, 16, 17, 19, and 21?23 exhibited potent inhibitions on NF-κB activation at 20 μM	10.1021/acs.jnatprod.5c00425 Journal of Natural Products

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