SCS-C007447

25-hydroxyfumitremorgin B

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

Back to List

Chemical Structure

Loading 3D structure...

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

495.6 Da

Threshold ≤ 500

ALogP

2.16

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C27H33N3O6

Molecular Weight:

495.5760 Da

SMILES:

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

InChIKey:

                        FIICBVXELZPDTN-JKNJHFESSA-N
                        
                    

InChI:

InChI=1S/C27H33N3O6/c1-15(2)12-21-23-22(18-8-7-17(36-4)13-20(18)28(23)11-9-16(3)14-31)24(32)27(35)26(34)29-10-5-6-19(29)25(33)30(21)27/h7-9,12-13,19,21,24,31-32,35H,5-6,10-11,14H2,1-4H3/b16-9-/t19-,21-,24-,27+/m0/s1

Calculated Properties

ALogP:

2.165 lipophilicity

TPSA:

115.47 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (2 aromatic)

Chiral Centers:

Fsp³:

0.4815 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007447

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

Back to Compounds