SCS-C008258

phakellistatin 18

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

Chemical Structure

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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.

Download: SDF SMILES

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/np9008267 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

828.0 Da

Threshold ≤ 500

ALogP

2.20

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (MW) — borderline drug-like

Chemical Properties

Molecular Formula:

C45H61N7O8

Molecular Weight:

828.0240 Da

SMILES:

CCC(C)[C@@H]1NC(=O)[C@@H]2CCCN2C(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C(C)CC)NC(=O)[C@@H]2CCCN2C(=O)[C@@H](Cc2ccccc2)NC1=O

InChIKey:

                        PPBMKOPYMFQWPM-QEHJJXGLSA-N
                        
                    

InChI:

InChI=1S/C45H61N7O8/c1-5-27(3)37-42(57)47-33(25-29-13-8-7-9-14-29)44(59)51-23-11-17-36(51)41(56)49-38(28(4)6-2)45(60)52-24-12-15-34(52)39(54)46-32(26-30-18-20-31(53)21-19-30)43(58)50-22-10-16-35(50)40(55)48-37/h7-9,13-14,18-21,27-28,32-38,53H,5-6,10-12,15-17,22-26H2,1-4H3,(H,46,54)(H,47,57)(H,48,55)(H,49,56)/t27?,28?,32-,33+,34-,35-,36-,37-,38-/m0/s1

Calculated Properties

ALogP:

2.195 lipophilicity

TPSA:

197.56 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.5778 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008258

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	—	BEL-7402 cancer cell lines	Phakellistatins 17 (4) and 18 (5) showed no cytotoxicity against the cancer cell lines P388 and BEL-7402 in this assay.	10.1021/np9008267 Journal of Natural Products

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