SCS-C007451

okaramine T

Pathway: Alkaloids | Amino acids and Peptides Superclass: Peptide alkaloids Class: Indole diketopiperazine alkaloids (L-Trp, L-Trp)

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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

456.5 Da

Threshold ≤ 500

ALogP

2.91

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H28N4O3

Molecular Weight:

456.5460 Da

SMILES:

C=CC(C)(C)c1[nH]c2ccccc2c1C[C@@H]1NC(=O)[C@H]2C[C@@]3(O)c4ccccc4N[C@H]3N2C1=O

InChIKey:

                        VGGSHMCMMWNUQL-BEPULHBCSA-N
                        
                    

InChI:

InChI=1S/C27H28N4O3/c1-4-26(2,3)22-16(15-9-5-7-11-18(15)28-22)13-20-24(33)31-21(23(32)29-20)14-27(34)17-10-6-8-12-19(17)30-25(27)31/h4-12,20-21,25,28,30,34H,1,13-14H2,2-3H3,(H,29,32)/t20-,21+,25-,27+/m0/s1

Calculated Properties

ALogP:

2.913 lipophilicity

TPSA:

97.46 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (3 aromatic)

Chiral Centers:

Fsp³:

0.3333 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007451

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

Indole diketopiperazine alkaloids (L-Trp, L-Trp)

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 activity	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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