SCS-C008251
phakellistatin 16
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/np9008267
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
1037.1 Da
Threshold ≤ 500
ALogP
-4.36
Threshold ≤ 5
H-Bond Donors
14
Threshold ≤ 5
H-Bond Acceptors
14
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C48H68N12O14
Molecular Weight:
1037.1420 Da
SMILES:
CC(C)[C@@H]1NC(=O)[C@H](C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(=O)O)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@@H]2CCCN2C(=O)[C@H](Cc2ccc(O)cc2)NC(=O)[C@H]([C@@H](C)O)NC1=O
InChIKey:
HWZJEQDZVPMMCZ-CRKMPNTNSA-N
InChI:
InChI=1S/C48H68N12O14/c1-24(2)37-45(72)59-38(26(4)62)46(73)56-33(21-28-14-16-29(63)17-15-28)47(74)60-19-9-13-35(60)44(71)55-31(20-27-10-6-5-7-11-27)41(68)54-32(22-36(64)65)42(69)57-34(23-61)43(70)53-30(12-8-18-51-48(49)50)40(67)52-25(3)39(66)58-37/h5-7,10-11,14-17,24-26,30-35,37-38,61-63H,8-9,12-13,18-23H2,1-4H3,(H,52,67)(H,53,70)(H,54,68)(H,55,71)(H,56,73)(H,57,69)(H,58,66)(H,59,72)(H,64,65)(H4,49,50,51)/t25-,26+,30-,31-,32-,33-,34-,35-,37-,38-/m0/s1
Calculated Properties
ALogP:
-4.362 lipophilicity
TPSA:
415.50 Ų polar surface area
H-Bond Donors:
14
H-Bond Acceptors:
14
Rotatable Bonds:
13
Ring Count:
4
(2 aromatic)
Chiral Centers:
10
Fsp³:
0.5208 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008251
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 | P388 cancer cell line | 5.4 μM | 10.1021/np9008267 Journal of Natural Products |
| Antitumor | IC50 | BEL-7402 cancer cell line | 14.3 μM | 10.1021/np9008267 Journal of Natural Products |