SCS-C004928
versicamide A
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids
Class: Indole diketopiperazine alkaloids (L-Trp, L-Pro)
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
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
429.5 Da
Threshold ≤ 500
ALogP
4.03
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C26H27N3O3
Molecular Weight:
429.5200 Da
SMILES:
CC1(C)C=Cc2c(ccc3c4c([nH]c23)C(C)(C)/C=C\N2C(=O)C3=CCCN3C(=O)[C@@H]2C4)O1
InChIKey:
QYOAOUSBEQVWNW-QXFGJRORSA-N
InChI:
InChI=1S/C26H27N3O3/c1-25(2)11-13-29-19(24(31)28-12-5-6-18(28)23(29)30)14-17-15-7-8-20-16(21(15)27-22(17)25)9-10-26(3,4)32-20/h6-11,13,19,27H,5,12,14H2,1-4H3/b13-11-/t19-/m0/s1
Calculated Properties
ALogP:
4.027 lipophilicity
TPSA:
65.64 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
3
Rotatable Bonds:
0
Ring Count:
6
(2 aromatic)
Chiral Centers:
1
Fsp³:
0.3846 fraction sp³ carbon
Database Information
Compound ID:
SCS-C004928
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.