SCS-C008252

phakellistatin 17

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

916.2 Da

Threshold ≤ 500

ALogP

2.92

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:

C49H73N9O8

Molecular Weight:

916.1780 Da

SMILES:

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

InChIKey:

                        MZDYKBQADUUMIO-KJCFDAGBSA-N
                        
                    

InChI:

InChI=1S/C49H73N9O8/c1-9-29(7)40-48(65)58-23-15-20-38(58)46(63)55-41(30(8)10-2)49(66)57-22-14-19-37(57)45(62)52-35(25-31-26-50-33-17-12-11-16-32(31)33)43(60)53-39(28(5)6)47(64)56-21-13-18-36(56)44(61)51-34(24-27(3)4)42(59)54-40/h11-12,16-17,26-30,34-41,50H,9-10,13-15,18-25H2,1-8H3,(H,51,61)(H,52,62)(H,53,60)(H,54,59)(H,55,63)/t29-,30-,34-,35-,36-,37-,38-,39-,40-,41-/m0/s1

Calculated Properties

ALogP:

2.915 lipophilicity

TPSA:

222.22 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.6735 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008252

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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