SCS-C007453
cyclo(L-Trp-L-Trp)
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids | Small peptides
Class: Dipeptides | Indole diketopiperazine alkaloids (L-Trp, L-Trp)
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
Penicillium brefeldianum GXIMD 02511
(NA)
Original source name: Penicillium brefeldianum | Penicillium brefeldianum GXIMD 02511
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium brefeldianum
South China Sea
DOI:
10.1021/acs.jnatprod.5c00425
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
372.4 Da
Threshold ≤ 500
ALogP
2.42
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H20N4O2
Molecular Weight:
372.4280 Da
SMILES:
O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N[C@H]1Cc1c[nH]c2ccccc12
InChIKey:
DNHODRZUCGXYKU-PMACEKPBSA-N
InChI:
InChI=1S/C22H20N4O2/c27-21-19(9-13-11-23-17-7-3-1-5-15(13)17)25-22(28)20(26-21)10-14-12-24-18-8-4-2-6-16(14)18/h1-8,11-12,19-20,23-24H,9-10H2,(H,25,28)(H,26,27)/t19-,20-/m0/s1
Calculated Properties
ALogP:
2.418 lipophilicity
TPSA:
89.78 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
2
Rotatable Bonds:
4
Ring Count:
5
(4 aromatic)
Chiral Centers:
2
Fsp³:
0.1818 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007453
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Peptide alkaloids
Small peptides
NPClassifier Class:
Dipeptides
Indole diketopiperazine alkaloids (L-Trp, L-Trp)
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.