SCS-C000248
stephacidin B
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
Aspergillus ochraceus
(fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus ochraceus
South China Sea
DOI:
10.1039/c9ra03640g
· RSC Advances
Drug-likeness (Lipinski Ro5)
Molecular Weight
891.0 Da
Threshold ≤ 500
ALogP
5.79
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C52H54N6O8
Molecular Weight:
891.0000 Da
SMILES:
CC1(C)C=Cc2c(ccc3c2[N+]([O-])=C2C(C)(C)[C@@H]4CC56CCCN5C(=O)[C@]4(NC6=O)[C@H]4N5C(=O)[C@@]67CCCN6C(=O)[C@@]56[C@H](c5c(n(O)c8c9c(ccc58)OC(C)(C)C=C9)C(C)(C)[C@@H]6C7)[C@]234)O1
InChIKey:
ZKJYVORSURCOMD-WYLTXJKKSA-N
InChI:
InChI=1S/C52H54N6O8/c1-44(2)19-15-25-29(65-44)13-11-27-33-36-50-28-12-14-30-26(16-20-45(3,4)66-30)35(28)58(64)38(50)47(7,8)31-23-48-17-9-21-54(48)42(61)51(31,53-40(48)59)39(50)56-41(60)49-18-10-22-55(49)43(62)52(36,56)32(24-49)46(5,6)37(33)57(63)34(25)27/h11-16,19-20,31-32,36,39,63H,9-10,17-18,21-24H2,1-8H3,(H,53,59)/t31-,32-,36+,39-,48?,49-,50-,51+,52+/m0/s1
Calculated Properties
ALogP:
5.790 lipophilicity
TPSA:
159.72 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
9
Rotatable Bonds:
0
Ring Count:
17
(3 aromatic)
Chiral Centers:
9
Fsp³:
0.5577 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000248
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
Activity values are displayed only when a quantitative or clearly reported result is available.
Tested organisms, cell lines and molecular targets are shown under Target / model.
| Activity | Assay | Target / model | Result | Reference |
|---|---|---|---|---|
| Antitumor | inhibition_percent | tumor cell lines | > 95.0 % | 10.1039/c9ra03640g RSC Advances |