SCS-C004440
versicamide C
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
477.6 Da
Threshold ≤ 500
ALogP
2.85
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C27H31N3O5
Molecular Weight:
477.5610 Da
SMILES:
CO[C@]12C(=O)N3/C=C\C(C)(C)c4[nH]c5c6c(ccc5c4C[C@H]3C(=O)N1CC[C@@H]2O)OC(C)(C)C=C6
InChIKey:
SQAOYGKFCFICRF-STZKJYTGSA-N
InChI:
InChI=1S/C27H31N3O5/c1-25(2)11-13-29-18(23(32)30-12-9-20(31)27(30,34-5)24(29)33)14-17-15-6-7-19-16(21(15)28-22(17)25)8-10-26(3,4)35-19/h6-8,10-11,13,18,20,28,31H,9,12,14H2,1-5H3/b13-11-/t18-,20-,27+/m0/s1
Calculated Properties
ALogP:
2.846 lipophilicity
TPSA:
95.10 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
5
Rotatable Bonds:
1
Ring Count:
6
(2 aromatic)
Chiral Centers:
3
Fsp³:
0.4815 fraction sp³ carbon
Database Information
Compound ID:
SCS-C004440
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.