SCS-C000658

Phakellisin D

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

Chemical Structure

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Download: SDF SMILES

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

803.0 Da

Threshold ≤ 500

ALogP

1.40

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C43H58N6O9

Molecular Weight:

802.9700 Da

SMILES:

CC[C@H](C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H]2CCCN2C(=O)[C@@H]2CCCN2C(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)OC(=O)[C@H](Cc2ccccc2)NC1=O

InChIKey:

                        HUBQUBKWTURLNC-IESXPROYSA-N
                        
                    

InChI:

InChI=1S/C43H58N6O9/c1-5-26(3)35-39(53)45-31(24-29-17-11-8-12-18-29)43(57)58-36(27(4)6-2)40(54)46-32(25-50)41(55)49-22-14-20-34(49)42(56)48-21-13-19-33(48)38(52)44-30(37(51)47-35)23-28-15-9-7-10-16-28/h7-12,15-18,26-27,30-36,50H,5-6,13-14,19-25H2,1-4H3,(H,44,52)(H,45,53)(H,46,54)(H,47,51)/t26-,27-,30-,31-,32-,33-,34-,35-,36-/m0/s1

Calculated Properties

ALogP:

1.403 lipophilicity

TPSA:

203.55 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (2 aromatic)

Chiral Centers:

Fsp³:

0.5581 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000658

NPClassifier Pathway:

Amino acids and Peptides Polyketides

NPClassifier Superclass:

Oligopeptides

NPClassifier Class:

Cyclic peptides Depsipeptides

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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