SCS-C008256
phakellistatin 13
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.
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
798.9 Da
Threshold ≤ 500
ALogP
0.43
Threshold ≤ 5
H-Bond Donors
7
Threshold ≤ 5
H-Bond Acceptors
8
Threshold ≤ 10
2 violations (MW, HBD) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C42H54N8O8
Molecular Weight:
798.9420 Da
SMILES:
CC(C)C[C@@H]1NC(=O)[C@H](C(C)O)NC(=O)[C@@H]2CCCN2C(=O)CNC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](Cc2c[nH]c3ccccc23)NC1=O
InChIKey:
GCYCNNNVEBIXIM-SUJHIFHOSA-N
InChI:
InChI=1S/C42H54N8O8/c1-24(2)19-30-38(54)47-32(21-27-22-43-29-14-8-7-13-28(27)29)42(58)50-18-10-16-34(50)39(55)45-31(20-26-11-5-4-6-12-26)37(53)44-23-35(52)49-17-9-15-33(49)40(56)48-36(25(3)51)41(57)46-30/h4-8,11-14,22,24-25,30-34,36,43,51H,9-10,15-21,23H2,1-3H3,(H,44,53)(H,45,55)(H,46,57)(H,47,54)(H,48,56)/t25?,30-,31-,32-,33-,34-,36-/m0/s1
Calculated Properties
ALogP:
0.431 lipophilicity
TPSA:
222.14 Ų polar surface area
H-Bond Donors:
7
H-Bond Acceptors:
8
Rotatable Bonds:
7
Ring Count:
6
(3 aromatic)
Chiral Centers:
7
Fsp³:
0.5000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008256
NPClassifier Pathway:
Amino acids and Peptides
NPClassifier Superclass:
Oligopeptides
NPClassifier Class:
Cyclic peptides
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
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 | — | — | Our previous studies on the chemical constituents of the marine sponge Phakellia fusca collected from the South China Sea led to the isolation of a cytotoxic cyclopeptide, phakellistatin 13 (1). | 10.1021/np9008267 Journal of Natural Products |