SCS-C007445

6,7-dehydropaxilline O

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

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

433.5 Da

Threshold ≤ 500

ALogP

4.08

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H31NO4

Molecular Weight:

433.5480 Da

SMILES:

CC(C)(O)[C@H]1OC2=CC[C@@]3(C)[C@@](O)(CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O

InChIKey:

                        CVGQHEQXHTWRKO-MIEPDMAISA-N
                        
                    

InChI:

InChI=1S/C27H31NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,10,14-15,23,28,30-31H,9,11-13H2,1-4H3/t15-,23-,25+,26+,27+/m0/s1

Calculated Properties

ALogP:

4.082 lipophilicity

TPSA:

82.55 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.5185 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007445

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	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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