SCS-C000659

Phakellisin E

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

Chemical Structure

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Source Information

Phakellia sp. (NA)

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

Yongxing Island

DOI: 10.1016/j.bioorg.2023.106699 · Bioorganic Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

701.3 Da

Threshold ≤ 500

ALogP

-2.84

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:

C33H47N7O10

Molecular Weight:

701.3400 Da

SMILES:

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

InChIKey:

                        XNHPWKCZHUILQK-HSRJJSSESA-N
                        
                    

InChI:

InChI=1S/C33H47N7O10/c1-16-27(44)34-17(2)28(45)36-22(15-20-9-11-21(43)12-10-20)29(46)38-26(19(4)42)33(50)40-14-6-8-24(40)32(49)39-13-5-7-23(39)30(47)37-25(18(3)41)31(48)35-16/h9-12,16-19,22-26,41-43H,5-8,13-15H2,1-4H3,(H,34,44)(H,35,48)(H,36,45)(H,37,47)(H,38,46)/t16-,17-,18+,19+,22-,23-,24-,25-,26-/m0/s1

Calculated Properties

ALogP:

-2.844 lipophilicity

TPSA:

246.81 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (1 aromatic)

Chiral Centers:

Fsp³:

0.6061 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000659

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	—	A2780; PC9; HePG2; Du145	cytotoxic activity	10.1016/j.bioorg.2023.106699 Bioorganic Chemistry

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