SCS-C007436

verruculogen

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

511.6 Da

Threshold ≤ 500

ALogP

2.86

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C27H33N3O7

Molecular Weight:

511.5750 Da

SMILES:

COc1ccc2c3c4n(c2c1)[C@@H](C=C(C)C)OOC(C)(C)C[C@@H]4N1C(=O)[C@@H]2CCCN2C(=O)[C@]1(O)[C@H]3O

InChIKey:

                        LRXYHMMJJCTUMY-GWXUGYLUSA-N
                        
                    

InChI:

InChI=1S/C27H33N3O7/c1-14(2)11-20-29-18-12-15(35-5)8-9-16(18)21-22(29)19(13-26(3,4)37-36-20)30-24(32)17-7-6-10-28(17)25(33)27(30,34)23(21)31/h8-9,11-12,17,19-20,23,31,34H,6-7,10,13H2,1-5H3/t17-,19-,20+,23-,27+/m0/s1

Calculated Properties

ALogP:

2.855 lipophilicity

TPSA:

113.70 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.5556 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007436

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 activity	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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