SCS-C007439

prenylcyclotryprostatin B

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

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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

493.6 Da

Threshold ≤ 500

ALogP

3.85

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C28H35N3O5

Molecular Weight:

493.6040 Da

SMILES:

COc1ccc2c3c(n(CC=C(C)C)c2c1)[C@H](C=C(C)C)N1C(=O)[C@@H]2CCCN2C(=O)[C@@]1(O)[C@H]3OC

InChIKey:

                        ZWMOSRAJNUGNFO-RZVQSFSYSA-N
                        
                    

InChI:

InChI=1S/C28H35N3O5/c1-16(2)11-13-29-21-15-18(35-5)9-10-19(21)23-24(29)22(14-17(3)4)31-26(32)20-8-7-12-30(20)27(33)28(31,34)25(23)36-6/h9-11,14-15,20,22,25,34H,7-8,12-13H2,1-6H3/t20-,22-,25-,28-/m0/s1

Calculated Properties

ALogP:

3.846 lipophilicity

TPSA:

84.24 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (2 aromatic)

Chiral Centers:

Fsp³:

0.5000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007439

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

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

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
Bone metabolism / Osteoclast	inhibitory	osteoclast	5, 6, and 16 suppressed RANKL-induced osteoclast differentiation in bone marrow macrophages (BMMs) in a dose-dependent manner without obvious cytotoxicity	10.1021/acs.jnatprod.5c00425 Journal of Natural Products

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