SCS-C007449

spirobrefeldin A

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

445.5 Da

Threshold ≤ 500

ALogP

-0.53

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H27N3O7

Molecular Weight:

445.4720 Da

SMILES:

COc1ccc2c(c1)N[C@@]1(C2=O)[C@H](CC(C)(C)O)N2C(=O)[C@@H]3CCCN3C(=O)[C@]2(O)[C@H]1O

InChIKey:

                        HMPBQKDSUXQAJG-KCDHAKLCSA-N
                        
                    

InChI:

InChI=1S/C22H27N3O7/c1-20(2,30)10-15-21(16(26)12-7-6-11(32-3)9-13(12)23-21)18(28)22(31)19(29)24-8-4-5-14(24)17(27)25(15)22/h6-7,9,14-15,18,23,28,30-31H,4-5,8,10H2,1-3H3/t14-,15-,18-,21+,22+/m0/s1

Calculated Properties

ALogP:

-0.532 lipophilicity

TPSA:

139.64 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (1 aromatic)

Chiral Centers:

Fsp³:

0.5909 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007449

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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