SCS-C007443

brefeldindole D

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

553.7 Da

Threshold ≤ 500

ALogP

2.95

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

2 violations (MW, HBD) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C32H43NO7

Molecular Weight:

553.6960 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)O[C@@]4(O)C[C@H](O)[C@]2(C)[C@@]31C

InChIKey:

                        LYJYQRYNQLQVLR-QOWARFQESA-N
                        
                    

InChI:

InChI=1S/C32H43NO7/c1-27(2,36)12-10-17-8-7-9-20-24(17)19-14-18-11-13-31(38)22-15-21(34)26(28(3,4)37)40-32(22,39)16-23(35)30(31,6)29(18,5)25(19)33-20/h7-9,15,18,23,26,33,35-39H,10-14,16H2,1-6H3/t18-,23-,26-,29+,30+,31+,32-/m0/s1

Calculated Properties

ALogP:

2.951 lipophilicity

TPSA:

143.24 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.6562 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007443

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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