SCS-C007431

brefeldindole A

Pathway: Alkaloids | Terpenoids Superclass: Tryptophan alkaloids Class: Indole-Diterpenoid alkaloids (Penitrems)

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

519.7 Da

Threshold ≤ 500

ALogP

4.79

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C32H41NO5

Molecular Weight:

519.6820 Da

SMILES:

CC(C)(O)CCc1cccc2[nH]c3c(c12)C[C@@H]1CC[C@@]2(O)C4=CC(=O)[C@@H](C(C)(C)O)OC4=CC[C@]2(C)[C@@]31C

InChIKey:

                        BEWLARAMZJFSEK-LGTSKZSNSA-N
                        
                    

InChI:

InChI=1S/C32H41NO5/c1-28(2,35)13-10-18-8-7-9-22-25(18)20-16-19-11-15-32(37)21-17-23(34)27(29(3,4)36)38-24(21)12-14-30(32,5)31(19,6)26(20)33-22/h7-9,12,17,19,27,33,35-37H,10-11,13-16H2,1-6H3/t19-,27-,30+,31+,32+/m0/s1

Calculated Properties

ALogP:

4.785 lipophilicity

TPSA:

102.78 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.5938 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007431

NPClassifier Pathway:

Alkaloids Terpenoids

NPClassifier Superclass:

Tryptophan alkaloids

NPClassifier Class:

Indole-Diterpenoid alkaloids (Penitrems)

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	enzyme inhibition	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