SCS-C007340

fuscasin C

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

761.9 Da

Threshold ≤ 500

ALogP

0.00

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:

C39H51N7O9

Molecular Weight:

761.8770 Da

SMILES:

CC(C)C[C@@H]1NC(=O)[C@H](C)NC(=O)[C@@H]2CCCN2C(=O)CNC(=O)C(Cc2ccc(O)cc2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](Cc2ccc(O)cc2)NC1=O

InChIKey:

                        RNNFJYLCTAGGMS-CIMYTASASA-N
                        
                    

InChI:

InChI=1S/C39H51N7O9/c1-22(2)18-28-36(52)44-30(20-25-10-14-27(48)15-11-25)39(55)46-17-5-7-32(46)38(54)43-29(19-24-8-12-26(47)13-9-24)35(51)40-21-33(49)45-16-4-6-31(45)37(53)41-23(3)34(50)42-28/h8-15,22-23,28-32,47-48H,4-7,16-21H2,1-3H3,(H,40,51)(H,41,53)(H,42,50)(H,43,54)(H,44,52)/t23-,28-,29?,30-,31-,32-/m0/s1

Calculated Properties

ALogP:

0.000 lipophilicity

TPSA:

226.58 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (2 aromatic)

Chiral Centers:

Fsp³:

0.5128 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007340

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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