SCS-C004470
(+)-variecolortin A
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Peptide alkaloids
Class: Indole diketopiperazine alkaloids (L-Trp, L-Ala)
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
Eurotium sp.
(gorgonian-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Eurotium
Species
NA
South China Sea
DOI:
10.1021/acs.orglett.8b01880
· Organic Letters
Drug-likeness (Lipinski Ro5)
Molecular Weight
651.7 Da
Threshold ≤ 500
ALogP
3.82
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C36H33N3O9
Molecular Weight:
651.6720 Da
SMILES:
C=CC(C)(C)c1[nH]c2ccccc2c1/C=C1\NC(=O)[C@@]23C[C@@H](c4c(c(C)cc(O)c4C(=O)OC)O2)[C@@]2(CC(=O)C=C(OC)C2=O)N3C1=O
InChIKey:
QZPKRXOBZYTEBJ-OXRLJIRASA-N
InChI:
InChI=1S/C36H33N3O9/c1-7-34(3,4)29-20(19-10-8-9-11-22(19)37-29)14-23-31(43)39-35(15-18(40)13-25(46-5)30(35)42)21-16-36(39,33(45)38-23)48-28-17(2)12-24(41)27(26(21)28)32(44)47-6/h7-14,21,37,41H,1,15-16H2,2-6H3,(H,38,45)/b23-14-/t21-,35+,36+/m0/s1
Calculated Properties
ALogP:
3.819 lipophilicity
TPSA:
164.33 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
9
Rotatable Bonds:
5
Ring Count:
7
(3 aromatic)
Chiral Centers:
3
Fsp³:
0.3056 fraction sp³ carbon
Database Information
Compound ID:
SCS-C004470
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Peptide alkaloids
NPClassifier Class:
Indole diketopiperazine alkaloids (L-Trp, L-Ala)
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.