SCS-C000326

chrysogeamide B

Pathway: Amino acids and Peptides | Polyketides Superclass: Oligopeptides Class: Cyclic peptides | Depsipeptides | Lipopeptides

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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 chrysogenum (fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species Penicillium chrysogenum

South China Sea

DOI: 10.1021/acs.joc.8b02614 · The Journal of Organic Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

623.8 Da

Threshold ≤ 500

ALogP

2.34

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C32H57N5O7

Molecular Weight:

623.8000 Da

SMILES:

CCCCCC[C@H](C)[C@@H]1CC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)O1

InChIKey:

                        OSDSZHQNFBBDRR-MIABJUDESA-N
                        
                    

InChI:

InChI=1S/C32H57N5O7/c1-10-11-12-13-14-21(8)24-16-25(38)33-17-26(39)36-27(19(4)5)31(42)35-23(15-18(2)3)30(41)34-22(9)29(40)37-28(20(6)7)32(43)44-24/h18-24,27-28H,10-17H2,1-9H3,(H,33,38)(H,34,41)(H,35,42)(H,36,39)(H,37,40)/t21-,22-,23+,24-,27-,28-/m0/s1

Calculated Properties

ALogP:

2.342 lipophilicity

TPSA:

171.80 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

1 (0 aromatic)

Chiral Centers:

Fsp³:

0.8125 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000326

NPClassifier Pathway:

Amino acids and Peptides Polyketides

NPClassifier Superclass:

Oligopeptides

NPClassifier Class:

Cyclic peptides Depsipeptides Lipopeptides

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
Angiogenesis modulation	IC50	zebrafish embryo	1.0 μg/mL	10.1021/acs.joc.8b02614 The Journal of Organic Chemistry

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