SCS-C007437
12β-hydroxyverruculogen TR-2
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
429.5 Da
Threshold ≤ 500
ALogP
0.95
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H27N3O6
Molecular Weight:
429.4730 Da
SMILES:
COc1ccc2c3c([nH]c2c1)[C@H](CC(C)(C)O)N1C(=O)[C@@H]2CCCN2C(=O)[C@@]1(O)[C@H]3O
InChIKey:
PIWNJAZCHHBADQ-FEHLYQECSA-N
InChI:
InChI=1S/C22H27N3O6/c1-21(2,29)10-15-17-16(12-7-6-11(31-3)9-13(12)23-17)18(26)22(30)20(28)24-8-4-5-14(24)19(27)25(15)22/h6-7,9,14-15,18,23,26,29-30H,4-5,8,10H2,1-3H3/t14-,15-,18-,22-/m0/s1
Calculated Properties
ALogP:
0.947 lipophilicity
TPSA:
126.33 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
6
Rotatable Bonds:
3
Ring Count:
5
(2 aromatic)
Chiral Centers:
4
Fsp³:
0.5455 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007437
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.