SCS-C007444

brefeldindole G

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

Back to List

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

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

525.6 Da

Threshold ≤ 500

ALogP

1.98

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C27H31N3O8

Molecular Weight:

525.5580 Da

SMILES:

COc1ccc2c3c4n(c2c1)[C@@H](/C=C(\C)CO)OOC(C)(C)C[C@@H]4N1C(=O)[C@@H]2CCCN2C(=O)[C@]1(O)C3=O

InChIKey:

                        PPWUWOSLHBDXRF-QQNSLWBGSA-N
                        
                    

InChI:

InChI=1S/C27H31N3O8/c1-14(13-31)10-20-29-18-11-15(36-4)7-8-16(18)21-22(29)19(12-26(2,3)38-37-20)30-24(33)17-6-5-9-28(17)25(34)27(30,35)23(21)32/h7-8,10-11,17,19-20,31,35H,5-6,9,12-13H2,1-4H3/b14-10+/t17-,19-,20+,27+/m0/s1

Calculated Properties

ALogP:

1.977 lipophilicity

TPSA:

130.77 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.5185 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007444

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

Back to Compounds