SCS-C007435
24-hydroxyverruculogen
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
527.6 Da
Threshold ≤ 500
ALogP
1.83
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C27H33N3O8
Molecular Weight:
527.5740 Da
SMILES:
COc1ccc2c3c4n(c2c1)[C@@H](/C=C(\C)CO)OOC(C)(C)C[C@@H]4N1C(=O)[C@@H]2CCCN2C(=O)[C@]1(O)[C@H]3O
InChIKey:
OPUYAZPZORIADD-JKPGSCGLSA-N
InChI:
InChI=1S/C27H33N3O8/c1-14(13-31)10-20-29-18-11-15(36-4)7-8-16(18)21-22(29)19(12-26(2,3)38-37-20)30-24(33)17-6-5-9-28(17)25(34)27(30,35)23(21)32/h7-8,10-11,17,19-20,23,31-32,35H,5-6,9,12-13H2,1-4H3/b14-10+/t17-,19-,20+,23-,27+/m0/s1
Calculated Properties
ALogP:
1.827 lipophilicity
TPSA:
133.93 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
9
Rotatable Bonds:
3
Ring Count:
6
(2 aromatic)
Chiral Centers:
5
Fsp³:
0.5556 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007435
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.