SCS-C007339

fuscasin B

Pathway: Amino acids and Peptides Superclass: Oligopeptides Class: Cyclic peptides

Chemical Structure

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Source Information

Phakellia fusca (NA)

Kingdom Metazoa Phylum Porifera Class Demospongiae Order Axinellida Family Axinellidae Genus Phakellia Species Phakellia fusca

South China Sea

DOI: 10.1021/acs.jnatprod.8b01033 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

814.0 Da

Threshold ≤ 500

ALogP

-2.29

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

2 violations (MW, HBD) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C38H59N11O9

Molecular Weight:

813.9580 Da

SMILES:

CC(C)C[C@@H]1NC(=O)[C@H](C)NC(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CCCN2C1=O

InChIKey:

                        LMZMSBCNJSZAMX-YYNHRMGXSA-N
                        
                    

InChI:

InChI=1S/C38H59N11O9/c1-19(2)16-27-37(58)49-15-7-9-28(49)35(56)48-30(20(3)4)36(57)46-26(18-29(39)51)34(55)44-24(8-6-14-42-38(40)41)32(53)45-25(17-22-10-12-23(50)13-11-22)33(54)43-21(5)31(52)47-27/h10-13,19-21,24-28,30,50H,6-9,14-18H2,1-5H3,(H2,39,51)(H,43,54)(H,44,55)(H,45,53)(H,46,57)(H,47,52)(H,48,56)(H4,40,41,42)/t21-,24-,25-,26-,27-,28-,30-/m0/s1

Calculated Properties

ALogP:

-2.291 lipophilicity

TPSA:

320.13 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (1 aromatic)

Chiral Centers:

Fsp³:

0.6053 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007339

NPClassifier Pathway:

Amino acids and Peptides

NPClassifier Superclass:

Oligopeptides

NPClassifier Class:

Cyclic peptides

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
Antitumor	—	MCF-7, HeLa, NCI-H460, PC9, HepG2, SW480 cells	the remaining isolated compounds proved to be inactive at concentrations up to 20 μM	10.1021/acs.jnatprod.8b01033 Journal of Natural Products

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