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SCS-C008196

acremonpeptide B

Pathway: Amino acids and Peptides Superclass: Oligopeptides Class: Cyclic peptides | Lipopeptides
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Chemical Structure

Structure of acremonpeptide B
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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

Acremonium persicinum (NA)
Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Hypocreales Family Bionectriaceae Genus Verruciconidia Species Verruciconidia persicina
South China Sea
DOI: 10.1021/acs.jnatprod.9b00545  · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight
848.0 Da
Threshold ≤ 500
ALogP
-0.73
Threshold ≤ 5
H-Bond Donors
9
Threshold ≤ 5
H-Bond Acceptors
12
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:
C39H61N9O12
Molecular Weight:
847.9680 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](C)NC1=O
InChIKey:
OYHIMWDFLNYBRE-QOEOITBWSA-N
InChI:
InChI=1S/C39H61N9O12/c1-23(2)21-32-38(56)45-33(22-28-13-8-7-9-14-28)39(57)43-31(17-12-20-48(60)27(6)51)37(55)42-30(16-11-19-47(59)26(5)50)36(54)41-29(15-10-18-46(58)25(4)49)35(53)40-24(3)34(52)44-32/h7-9,13-14,23-24,29-33,58-60H,10-12,15-22H2,1-6H3,(H,40,53)(H,41,54)(H,42,55)(H,43,57)(H,44,52)(H,45,56)/t24-,29-,30-,31-,32-,33-/m0/s1
Calculated Properties
ALogP:
-0.729 lipophilicity
TPSA:
296.22 Ų polar surface area
H-Bond Donors:
9
H-Bond Acceptors:
12
Rotatable Bonds:
16
Ring Count:
2 (1 aromatic)
Chiral Centers:
6
Fsp³:
0.6154 fraction sp³ carbon

Database Information

Compound ID:
SCS-C008196
NPClassifier Pathway:
Amino acids and Peptides
NPClassifier Superclass:
Oligopeptides
NPClassifier Class:
Cyclic peptides Lipopeptides
Glycoside:
No
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
Antiviral EC50 herpes simplex virus 1 (HSV-1) 8.7 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
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Structure enlarged