SCS-C007493
4'-N-demethylvicenistatin
Pathway: Amino acids and Peptides | Polyketides
Superclass: Macrolides
Class: Macrolide lactams
Glycoside
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
Streptomyces parvus SCSIO Mla-L010
(NA)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces parvus
South China Sea
DOI:
10.1021/acs.jnatprod.1c01044
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
486.7 Da
Threshold ≤ 500
ALogP
4.72
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C29H46N2O4
Molecular Weight:
486.6970 Da
SMILES:
C/C1=C\C=C\CC[C@H](C)CNC(=O)/C=C/C=C/[C@H](C)[C@@H](O[C@H]2C[C@@H](O)[C@H](N)C(C)O2)C/C=C(\C)C1
InChIKey:
HSUGJXHDBMHSEW-JQZKWANBSA-N
InChI:
InChI=1S/C29H46N2O4/c1-20-11-7-6-8-12-22(3)19-31-27(33)14-10-9-13-23(4)26(16-15-21(2)17-20)35-28-18-25(32)29(30)24(5)34-28/h6-7,9-11,13-15,22-26,28-29,32H,8,12,16-19,30H2,1-5H3,(H,31,33)/b7-6+,13-9+,14-10+,20-11+,21-15+/t22-,23-,24?,25+,26-,28-,29+/m0/s1
Calculated Properties
ALogP:
4.718 lipophilicity
TPSA:
93.81 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
5
Rotatable Bonds:
2
Ring Count:
2
(0 aromatic)
Chiral Centers:
7
Fsp³:
0.6207 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007493
NPClassifier Pathway:
Amino acids and Peptides
Polyketides
NPClassifier Superclass:
Macrolides
NPClassifier Class:
Macrolide lactams
Glycoside:
Yes
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 |
|---|---|---|---|---|
| Antibacterial | MIC | panel of Gram-positive pathogens including MRSA, Bacillus subtilis BS01, Micrococcus luteus ML01, Staphylococcus aureus ATCC29213 | 0.13–0.5 μg/mL | 10.1021/acs.jnatprod.1c01044 Journal of Natural Products |
| Antimycobacterial | MIC | Mycobacterium smegmatis ATCC 607 | 4.0 μg/mL | 10.1021/acs.jnatprod.1c01044 Journal of Natural Products |
| Antibacterial | MIC | Helicobacter pylori G27, Helicobacter pylori 159 | 1.0–2.0 μg/mL | 10.1021/acs.jnatprod.1c01044 Journal of Natural Products |
| Antifungal | MIC | Candida albicans ATCC SC5314, Candida albicans C5, Cryptoccus neoformans ATCC 4906 | 1.0–2.0 μg/mL | 10.1021/acs.jnatprod.1c01044 Journal of Natural Products |
| Antitumor | IC50 | MCF7, HepG2, HeLa, A549, RKO, HL-60 cancer cell lines, L-02 normal hepatic cell line, BEAS2B normal bronchial epithelial cell line | — Structured numeric value is not available in this record; see the primary reference. | 10.1021/acs.jnatprod.1c01044 Journal of Natural Products |