SCS-C007338
fuscasin A
Pathway: Amino acids and Peptides
Superclass: Oligopeptides
Class: Cyclic peptides
Chemical Structure
Loading 3D structure...
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/acs.jnatprod.8b01033
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
733.9 Da
Threshold ≤ 500
ALogP
0.25
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
8
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C38H51N7O8
Molecular Weight:
733.8670 Da
SMILES:
CC[C@@H]1NC(=O)[C@H](Cc2ccccc2)N2C(=O)C[C@H](NC(=O)[C@@H]3CCCN3C(=O)[C@@H]3CCCN3C(=O)[C@@H]3CCCN3C(=O)[C@H](CC(C)C)NC1=O)C2=O
InChIKey:
BYSYDEDWVHDEKK-FLMSMKGQSA-N
InChI:
InChI=1S/C38H51N7O8/c1-4-24-32(47)40-25(19-22(2)3)35(50)43-17-9-14-28(43)38(53)44-18-10-15-29(44)37(52)42-16-8-13-27(42)33(48)41-26-21-31(46)45(36(26)51)30(34(49)39-24)20-23-11-6-5-7-12-23/h5-7,11-12,22,24-30H,4,8-10,13-21H2,1-3H3,(H,39,49)(H,40,47)(H,41,48)/t24-,25-,26-,27-,28-,29-,30-/m0/s1
Calculated Properties
ALogP:
0.254 lipophilicity
TPSA:
185.61 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
8
Rotatable Bonds:
5
Ring Count:
6
(1 aromatic)
Chiral Centers:
7
Fsp³:
0.6316 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007338
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 | IC50 | HepG2 cells | 4.6 μM | 10.1021/acs.jnatprod.8b01033 Journal of Natural Products |
| Antitumor | — | MCF-7; HeLa; NCI-H460; PC9; SW480 cells | whereas it did not show apparent inhibitory effects against the other five human cancer cell lines, MCF-7, HeLa, NCI-H460, PC9, and SW480 | 10.1021/acs.jnatprod.8b01033 Journal of Natural Products |
| Antitumor | — | nonmalignant cells | Encouragingly, 1 exhibited no cytotoxicity against nonmalignant cells even with a concentration up to 100 μM | 10.1021/acs.jnatprod.8b01033 Journal of Natural Products |