SCS-C007441

brefeldindole B

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

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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

551.7 Da

Threshold ≤ 500

ALogP

4.63

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C33H45NO6

Molecular Weight:

551.7240 Da

SMILES:

CO[C@]12CC[C@@]3(C)[C@@](O)(CC[C@H]4Cc5c([nH]c6cccc(CCC(C)(C)O)c56)[C@@]43C)C1=CC(=O)[C@@H](C(C)(C)O)O2

InChIKey:

                        QMZFUJYLUIZNPK-ANPMQXHUSA-N
                        
                    

InChI:

InChI=1S/C33H45NO6/c1-28(2,36)13-11-19-9-8-10-22-25(19)21-17-20-12-14-32(38)24-18-23(35)27(29(3,4)37)40-33(24,39-7)16-15-30(32,5)31(20,6)26(21)34-22/h8-10,18,20,27,34,36-38H,11-17H2,1-7H3/t20-,27-,30+,31+,32+,33-/m0/s1

Calculated Properties

ALogP:

4.634 lipophilicity

TPSA:

112.01 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.6667 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007441

NPClassifier Pathway:

Alkaloids Terpenoids

NPClassifier Superclass:

Tryptophan alkaloids

NPClassifier Class:

Indole-Diterpenoid alkaloids (Penitrems)

Glycoside:

Yes

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

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