SCS-C007895
berninamycin B
Pathway: Amino acids and Peptides
Superclass: Oligopeptides
Class: Cyclic peptides | RiPPs-Thiopeptides
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 sp. SCSIO 11878
(bacterium)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
NA
South China Sea
· 1396 m
· E 118°58.2475′, N 22°2.3689′
DOI:
10.1039/d1ob01759d
· Organic & Biomolecular Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
1130.1 Da
Threshold ≤ 500
ALogP
0.98
Threshold ≤ 5
H-Bond Donors
11
Threshold ≤ 5
H-Bond Acceptors
20
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C51H51N15O14S
Molecular Weight:
1130.1270 Da
SMILES:
C=C(NC(=O)C(=C)NC(=O)c1ccc2c(n1)-c1coc(n1)C(=C)NC(=O)C(=C)NC(=O)c1nc(oc1C)C(=C)NC(=O)[C@H](C(C)C)NC(=O)C(=C)NC(=O)c1nc(oc1C)/C(=C/C)NC(=O)[C@H]([C@@H](C)O)NC(=O)c1csc-2n1)C(N)=O
InChIKey:
VFTYJPKNFPTPRA-KFSKHFNISA-N
InChI:
InChI=1S/C51H51N15O14S/c1-13-29-50-66-36(27(12)80-50)47(77)56-22(7)41(71)63-33(18(2)3)44(74)58-24(9)49-65-35(26(11)79-49)46(76)55-21(6)40(70)57-23(8)48-61-31(16-78-48)37-28(51-62-32(17-81-51)43(73)64-34(25(10)67)45(75)60-29)14-15-30(59-37)42(72)54-20(5)39(69)53-19(4)38(52)68/h13-18,25,33-34,67H,4-9H2,1-3,10-12H3,(H2,52,68)(H,53,69)(H,54,72)(H,55,76)(H,56,77)(H,57,70)(H,58,74)(H,60,75)(H,63,71)(H,64,73)/b29-13-/t25-,33+,34+/m1/s1
Calculated Properties
ALogP:
0.983 lipophilicity
TPSA:
429.09 Ų polar surface area
H-Bond Donors:
11
H-Bond Acceptors:
20
Rotatable Bonds:
7
Ring Count:
6
(5 aromatic)
Chiral Centers:
3
Fsp³:
0.1961 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007895
NPClassifier Pathway:
Amino acids and Peptides
NPClassifier Superclass:
Oligopeptides
NPClassifier Class:
Cyclic peptides
RiPPs-Thiopeptides
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 |
|---|---|---|---|---|
| Antibacterial | MIC | Gram-positive bacteria | 0.2–4.0 μg mL?1 | 10.1039/d1ob01759d Organic & Biomolecular Chemistry |
| Antibacterial | MIC | Gram-negative bacteria | > 64.0 μg mL?1 | 10.1039/d1ob01759d Organic & Biomolecular Chemistry |