SCS-C007440
spirotryprostatin M
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
513.6 Da
Threshold ≤ 500
ALogP
1.46
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
8
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C27H35N3O7
Molecular Weight:
513.5910 Da
SMILES:
COc1ccc2c(c1)N[C@@]1(C2=O)[C@H](CC(C)(C)O)N2C(=O)[C@@H]3CCCN3C(=O)[C@]2(O)[C@H]1OCC=C(C)C
InChIKey:
LUFNRQGQLDZSAO-CVXVVRTLSA-N
InChI:
InChI=1S/C27H35N3O7/c1-15(2)10-12-37-23-26(21(31)17-9-8-16(36-5)13-18(17)28-26)20(14-25(3,4)34)30-22(32)19-7-6-11-29(19)24(33)27(23,30)35/h8-10,13,19-20,23,28,34-35H,6-7,11-12,14H2,1-5H3/t19-,20-,23-,26+,27+/m0/s1
Calculated Properties
ALogP:
1.459 lipophilicity
TPSA:
128.64 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
8
Rotatable Bonds:
6
Ring Count:
5
(1 aromatic)
Chiral Centers:
5
Fsp³:
0.5926 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007440
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.