SCS-C007448
asperfumigatin
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
Penicillium brefeldianum GXIMD 02511
(NA)
Original source name: Penicillium brefeldianum | Penicillium brefeldianum GXIMD 02511
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium brefeldianum
South China Sea
DOI:
10.1021/acs.jnatprod.5c00425
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
511.6 Da
Threshold ≤ 500
ALogP
2.03
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
8
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C27H33N3O7
Molecular Weight:
511.5750 Da
SMILES:
COc1ccc2c3c(n(C(=O)C=C(C)C)c2c1)[C@H](CC(C)(C)O)N1C(=O)[C@@H]2CCCN2C(=O)[C@]1(O)[C@H]3O
InChIKey:
ZWTKNACGKAVJKO-USSWKXFGSA-N
InChI:
InChI=1S/C27H33N3O7/c1-14(2)11-20(31)29-18-12-15(37-5)8-9-16(18)21-22(29)19(13-26(3,4)35)30-24(33)17-7-6-10-28(17)25(34)27(30,36)23(21)32/h8-9,11-12,17,19,23,32,35-36H,6-7,10,13H2,1-5H3/t17-,19-,23-,27+/m0/s1
Calculated Properties
ALogP:
2.027 lipophilicity
TPSA:
132.54 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
8
Rotatable Bonds:
4
Ring Count:
5
(2 aromatic)
Chiral Centers:
4
Fsp³:
0.5185 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007448
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.