SCS-C006775
cyclo-L-tryptophyl-L-proline
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids | Small peptides
Class: Dipeptides | Indole diketopiperazine alkaloids (L-Trp, L-Pro)
Chemical Structure
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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.
Source Information
Aspergillus sydowii
(coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus sydowii
South China Sea
DOI:
10.1177/1934578x1300800313
· Natural Product Communications
Drug-likeness (Lipinski Ro5)
Molecular Weight
283.3 Da
Threshold ≤ 500
ALogP
1.20
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C16H17N3O2
Molecular Weight:
283.3310 Da
SMILES:
O=C1N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N2CCCC12
InChIKey:
RYFZBPVMVYTEKZ-LSLKUGRBSA-N
InChI:
InChI=1S/C16H17N3O2/c20-15-14-6-3-7-19(14)16(21)13(18-15)8-10-9-17-12-5-2-1-4-11(10)12/h1-2,4-5,9,13-14,17H,3,6-8H2,(H,18,20)/t13-,14?/m0/s1
Calculated Properties
ALogP:
1.200 lipophilicity
TPSA:
65.20 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
2
Rotatable Bonds:
2
Ring Count:
4
(2 aromatic)
Chiral Centers:
2
Fsp³:
0.3750 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006775
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Peptide alkaloids
Small peptides
NPClassifier Class:
Dipeptides
Indole diketopiperazine alkaloids (L-Trp, L-Pro)
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 |
|---|---|---|---|---|
| Antifouling | settlement inhibition | Bugula neritina larvae | 9–16 were tested only towards B. neritina larvae because of the sample amount limitation... 6, 9, 13, and 16 towards B. neritina larvae | 10.1177/1934578x1300800313 Natural Product Communications |