SCS-C008192
acremonpeptide A
Pathway: Amino acids and Peptides
Superclass: Oligopeptides
Class: Cyclic peptides | Lipopeptides
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
Verruciconidia persicina
(NA)
Original source name: Acremonium persicinum
South China Sea
DOI:
10.1021/acs.jnatprod.9b00545
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
864.0 Da
Threshold ≤ 500
ALogP
-1.76
Threshold ≤ 5
H-Bond Donors
10
Threshold ≤ 5
H-Bond Acceptors
13
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C39H61N9O13
Molecular Weight:
863.9670 Da
SMILES:
CC(=O)N(O)CCC[C@@H]1NC(=O)[C@H](CCCN(O)C(C)=O)NC(=O)[C@H](CCCN(O)C(C)=O)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC1=O
InChIKey:
ZWTDABBYXDAIOL-FSJACQRISA-N
InChI:
InChI=1S/C39H61N9O13/c1-23(2)20-31-37(56)44-32(21-27-12-7-6-8-13-27)38(57)42-29(15-10-18-47(60)25(4)51)35(54)40-28(14-9-17-46(59)24(3)50)34(53)41-30(16-11-19-48(61)26(5)52)36(55)45-33(22-49)39(58)43-31/h6-8,12-13,23,28-33,49,59-61H,9-11,14-22H2,1-5H3,(H,40,54)(H,41,53)(H,42,57)(H,43,58)(H,44,56)(H,45,55)/t28-,29-,30-,31-,32-,33-/m0/s1
Calculated Properties
ALogP:
-1.756 lipophilicity
TPSA:
316.45 Ų polar surface area
H-Bond Donors:
10
H-Bond Acceptors:
13
Rotatable Bonds:
17
Ring Count:
2
(1 aromatic)
Chiral Centers:
6
Fsp³:
0.6154 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008192
NPClassifier Pathway:
Amino acids and Peptides
NPClassifier Superclass:
Oligopeptides
NPClassifier Class:
Cyclic peptides
Lipopeptides
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 |
|---|---|---|---|---|
| Antiviral | EC50 | herpes simplex virus 1 (HSV-1) | 16.0 μM | 10.1021/acs.jnatprod.9b00545 Journal of Natural Products |
| Antiviral | — | HSV-1 UL42 gene | — Structured numeric value is not available in this record; see the primary reference. | 10.1021/acs.jnatprod.9b00545 Journal of Natural Products |
| Antimicrobial | — | Panel of tested bacteria and fungi | 1?5 proved inactive in these assays at concentrations up to 100 μg/mL | 10.1021/acs.jnatprod.9b00545 Journal of Natural Products |