SCS-C004900
versicamide F
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids
Class: 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 versicolor
(coral-associated fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus versicolor
South China Sea
DOI:
10.1021/jo5010179
· The Journal of Organic Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
493.6 Da
Threshold ≤ 500
ALogP
2.23
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C27H31N3O6
Molecular Weight:
493.5600 Da
SMILES:
CO[C@]12C(=O)N3/C=C\C(C)(C)C4=Nc5c(ccc6c5C=CC(C)(C)O6)[C@@]4(O)C[C@H]3C(=O)N1CC[C@@H]2O
InChIKey:
SHFRGAMTKGGHOB-ZSEIGEJHSA-N
InChI:
InChI=1S/C27H31N3O6/c1-24(2)11-13-29-17(21(32)30-12-9-19(31)27(30,35-5)23(29)33)14-26(34)16-6-7-18-15(20(16)28-22(24)26)8-10-25(3,4)36-18/h6-8,10-11,13,17,19,31,34H,9,12,14H2,1-5H3/b13-11-/t17-,19-,26-,27+/m0/s1
Calculated Properties
ALogP:
2.235 lipophilicity
TPSA:
111.90 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
7
Rotatable Bonds:
1
Ring Count:
6
(1 aromatic)
Chiral Centers:
4
Fsp³:
0.5185 fraction sp³ carbon
Database Information
Compound ID:
SCS-C004900
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Peptide alkaloids
NPClassifier Class:
Indole diketopiperazine alkaloids (L-Trp, L-Pro)
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.