SCS-C004560
versicamide B
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
461.6 Da
Threshold ≤ 500
ALogP
4.09
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C27H31N3O4
Molecular Weight:
461.5620 Da
SMILES:
COC1CC(C)(C)Oc2ccc3c4c([nH]c3c21)C(C)(C)/C=C\N1C(=O)C2=CCCN2C(=O)[C@@H]1C4
InChIKey:
PPVBHFZUHWABJT-DTCAWYJKSA-N
InChI:
InChI=1S/C27H31N3O4/c1-26(2)10-12-30-18(25(32)29-11-6-7-17(29)24(30)31)13-16-15-8-9-19-21(22(15)28-23(16)26)20(33-5)14-27(3,4)34-19/h7-10,12,18,20,28H,6,11,13-14H2,1-5H3/b12-10-/t18-,20?/m0/s1
Calculated Properties
ALogP:
4.091 lipophilicity
TPSA:
74.87 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
4
Rotatable Bonds:
1
Ring Count:
6
(2 aromatic)
Chiral Centers:
2
Fsp³:
0.4815 fraction sp³ carbon
Database Information
Compound ID:
SCS-C004560
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.