SCS-C007450

okaramine I

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

452.5 Da

Threshold ≤ 500

ALogP

3.40

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H24N4O3

Molecular Weight:

452.5140 Da

SMILES:

CC1(C)/C=C\N2C(=O)[C@H]3C[C@@]4(O)c5ccccc5N[C@H]4N3C(=O)/C2=C/c2c1[nH]c1ccccc21

InChIKey:

                        CTRNZLRKISVIAG-LBJKZLEUSA-N
                        
                    

InChI:

InChI=1S/C27H24N4O3/c1-26(2)11-12-30-20(13-16-15-7-3-5-9-18(15)28-22(16)26)24(33)31-21(23(30)32)14-27(34)17-8-4-6-10-19(17)29-25(27)31/h3-13,21,25,28-29,34H,14H2,1-2H3/b12-11-,20-13-/t21-,25+,27-/m1/s1

Calculated Properties

ALogP:

3.396 lipophilicity

TPSA:

88.67 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (3 aromatic)

Chiral Centers:

Fsp³:

0.2593 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007450

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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