SCS-C000656

Phakellisin B

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

938.1 Da

Threshold ≤ 500

ALogP

1.45

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:

C50H67N9O9

Molecular Weight:

938.1400 Da

SMILES:

CC(C)C[C@@H]1NC(=O)[C@@H]2CCCN2C(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C(C)C)NC(=O)[C@H](Cc2c[nH]c3ccccc23)NC(=O)[C@@H]2CCCN2C1=O

InChIKey:

                        FEIZCWFQRQZRHZ-CMMQLLMOSA-N
                        
                    

InChI:

InChI=1S/C50H67N9O9/c1-28(2)24-37-48(66)57-21-11-18-38(57)45(63)53-36(26-32-27-51-34-17-10-9-16-33(32)34)44(62)55-41(29(3)4)49(67)58-22-12-19-39(58)46(64)52-35(25-31-14-7-6-8-15-31)43(61)56-42(30(5)60)50(68)59-23-13-20-40(59)47(65)54-37/h6-10,14-17,27-30,35-42,51,60H,11-13,18-26H2,1-5H3,(H,52,64)(H,53,63)(H,54,65)(H,55,62)(H,56,61)/t30-,35+,36+,37+,38+,39+,40+,41+,42+/m1/s1

Calculated Properties

ALogP:

1.447 lipophilicity

TPSA:

242.45 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (3 aromatic)

Chiral Centers:

Fsp³:

0.5600 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000656

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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