SCS-C008183
2,3-epoxyphomapyrrolidone C
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Tetramate alkaloids
Class: Pyrrocidine tetramate alkaloids
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
Microascus sp.
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Microascales
Family
Microascaceae
Genus
Microascus
Species
Microascus sp.
Offshore Hainan Island
· 18°11'N, 109°25'E
DOI:
10.1021/acs.jnatprod.3c00984
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
559.7 Da
Threshold ≤ 500
ALogP
3.82
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C34H41NO6
Molecular Weight:
559.7030 Da
SMILES:
CC1=C2[C@@H](C)[C@@]3(C)O[C@H]3[C@]2(C)[C@@H]2[C@@H]3Oc4ccc(cc4)C[C@]4(O)NC(=O)[C@]5(OC54)C(=O)[C@@H]2[C@@H]1[C@@H]1C[C@H](C)C[C@H](C)[C@H]13
InChIKey:
CRTXXKLOLSOMMT-QPDCRFPCSA-N
InChI:
InChI=1S/C34H41NO6/c1-14-11-15(2)21-20(12-14)22-16(3)24-17(4)32(6)28(40-32)31(24,5)25-23(22)27(36)34-29(41-34)33(38,35-30(34)37)13-18-7-9-19(10-8-18)39-26(21)25/h7-10,14-15,17,20-23,25-26,28-29,38H,11-13H2,1-6H3,(H,35,37)/t14-,15+,17-,20-,21-,22+,23-,25+,26-,28+,29?,31+,32-,33-,34+/m1/s1
Calculated Properties
ALogP:
3.819 lipophilicity
TPSA:
100.69 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
6
Rotatable Bonds:
0
Ring Count:
10
(1 aromatic)
Chiral Centers:
15
Fsp³:
0.7059 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008183
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Tetramate alkaloids
NPClassifier Class:
Pyrrocidine tetramate alkaloids
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 |
|---|---|---|---|---|
| Enzyme inhibition | IC50 | PTP1B | 42.0 μM | 10.1021/acs.jnatprod.3c00984 Journal of Natural Products |
| Enzyme inhibition | IC50 | PTPSig | 38.0 μM | 10.1021/acs.jnatprod.3c00984 Journal of Natural Products |
| Antitumor | IC50 | H1975 and HepG2 cell lines | > 33.0 μM | 10.1021/acs.jnatprod.3c00984 Journal of Natural Products |